In this episode of the B2B Go-To-Market Leaders Podcast, Vijay Damojipurapu sits down with Gamiel Gran, Partner at Mayfield, to explore how decades of GTM experience—from IBM and Oracle to BEA Software and now venture capital—have shaped his philosophy on customer-centric growth and founder leadership.

Gamiel shares timeless lessons from building sales teams, scaling enterprise software in the early internet era, and coaching today’s AI-first founders through the next great technology shift. His message is simple but profound: it’s not about you—it’s about them.

They dive into:

• How curiosity and empathy separate great salespeople from quota chasers.
  
• Lessons from IBM’s legendary consultative sales training and Oracle’s “win at all costs” culture.
  
• The importance of founder clarity—why every word you say shapes how your team sells.
  
• How defining who not to sell to creates stronger product-market fit.
  
• The discipline of persona mapping: knowing your buyer so well you could do their job.
  
• Why AI isn’t just another wave—but a complete redesign of the IT and GTM stack.
  
• How agentic workflows will change selling, buying, and business process itself.
  
• Why founders must balance open-mindedness with focus—clarity is leadership.
  
• And the advice Gamiel gives every entrepreneur: Be your own North Star.
  

From fax-era product-led growth to AI-native go-to-market design, this conversation is a masterclass in how technology, empathy, and leadership evolve together.

Connect with Gamiel Gran on LinkedIn

Connect with Vijay Damojipurapu on LinkedIn

Listen To The Episode:

GTM In The AI Era: 30 Years of Lessons with Mayfield’s Gamiel Gran

I’ll again start off with my signature question, which is how do you view and define go-to-market?

So I love it when you ask this question. And honestly, I look at it first as a holistic strategy that kind of unites together product, marketing, sales, and of course, customer success. In a way that ensures we eventually our solutions, our products that we build reaches the right audience and is able to generate value and business outcomes to our clients.

Now, I said strategy. I think also execution is a very big part of that as well. You got to have both. So strategy and execution. And coming from customer success, I have to add the customer’s success angle of this topic.

I would also say there’s kind of four points. I look at it from my perspective. One, as customer success, we need to understand the messaging. Are customers here throughout the marketing funnel, during sales? What are the expectations from the products that they purchase from us? The second and probably one of the most important points is aligning the onboarding as well. What happens after the sales, that’s on us. And that has to be executed the best way possible.

It’s so easy to miss that critical point. We have to deliver value fast. And to do that, you need to understand their expectations. What are they coming to get from your product? In order to deliver the best onboarding experience and obviously to get live and get value from the product as soon as you can. The third point is building the collaboration. So I said the kind of the four main teams that are involved, but you have to build a very good collaboration. It never stops. And companies that succeed have this good collaboration. We don’t work in silos.

And the fourth point is crafting this journey. Customer success also, we don’t operate in a vacuum. So we need to understand the entire journey.How does the company land the customer in? How do we build the onboarding, the adoption? How do we build the expansion, the upselling motion together with sales? And obviously the renewal. So it’s a never ending journey. We still need marketing throughout this cycle.

We need sales, account management. We have to think about this process as well. So that’s my kind of summary of GTM and this is how I look at it.

Yeah, love it. In fact, I’m so glad that we now have a customer success angle and lens to this, which was missing from the show until now. So that’s bad on me, but I’m going to fix it going forward.

The reason why I say I love to have a customer success angle, which you articulated so well, I believe in your points, two, three, and four, especially, right? The first one, pretty much everyone on the show talk about customer problem and building a product that solves the customer problems. I get it. Everyone gets it.

I think that’s a prerequisite. But what’s not been emphasized so far on this show are the points number two, three, and four. Points two around onboarding.

So successful onboarding is critical. That’s one for sure. The next is a collaboration.

I mean, when you said collaboration, I was thinking external, which is customer success and the customers, but you also emphasized collaboration internally, especially with sales and product and not so much on marketing, but I understand where you’re coming from. And the fourth angle is thinking about the success of the customer, but at the same time, how you as a team, all of you can increase and should increase the adoption, which will translate to upsell, renewal, and so on.

That’s the base. And then when I said collaboration, internal collaboration, that’s where sometimes company miss. So obviously our job is to collaborate with customer. That’s the essence of customer success.

But again, you have to build this partnership within the company as well. Good leaders, they don’t forget. This is what needs to be done as well.

It’s not everything is on us. Not everything is customer success, churn and renewal problems and expansion. That’s a company goal. We are blue that kind of stick everything together.

And something that I’ve started noticing and I’ve been getting validation when I speak to other go-to-market leaders and even from an exit is to the detriment of the company’s growth and even to the detriment of customer being valued. I see a lot of emphasis within the B2B go-to-market motion.

I mean, a lot of emphasis is being placed on new logo acquisition, not so much on your existing customer base. Your thoughts on that, Alon?

You’re so right. I have to say, I see this shifting and I see more and more understanding this.

It used to be the situation a few years ago. I do see it shifts and change. There’s a big realization that your existing revenue can generate much more.

And I see more teams of account management and more collaboration between customer success and sales. But I think that’s probably the biggest drivers for revenue as well. Again, it also depends on the size of the company and its status.
Obviously for startups, you have to drive for new revenue to come in as well. But generating revenue from your existing customer base, by the way, in my view, it’s not just for the revenue sake. If your customers are not growing, there’s a good chance they won’t renew.

So successful customers, they use your product, they need more and more features, more licenses. You want to see, you have to build this growth as well. I do see this shift.

I think it’s there. The understanding is already happening. Where there’s always a struggle or a dilemma is who’s driving the upsell or the expansion motion.

Is it the customer success managers? Is it on the account executives? Do you have to build an account management team? So that’s a question, by the way. And by the way, I don’t think there’s a silver bullet to this question as well. It depends on the state of your company, how big the company is, where you are in your journey, how complex your product.

Wait, if your product is very technical, you want your CSMs to be technical as well. And at the end of the day, I see customer success, or at least the customer success managers role as a consultant, someone who brings value to the table. And to do that, you have to understand the product well enough and be able to advise.

And if you’re able to build this balance between consulting and pushing for the expansion eventually, then you’re succeeding. It’s something breaking those two apart, build a good partnership between a CSM or AM or account executives, then it works really well.

Now that’s a great point you mentioned, Alon, which is for a customer to be successful, the CS team has to act as trusted advisors. And that starts with having a good knowledge around the product and helping them get onboarded successfully and improve the adoption internally. I know we can go down this rabbit hole more.

I just add, I think definitely the CSMs are in the best position to identify potential. They know their customers best, they’re able to advise, they know to find those opportunities, whether if they’re eventually doing the commercial negotiation, that’s a different topic. But they have to have this mindset of looking for growth. They have to.

Excellent. All right. I’m sure we’ll get into a lot of those topics and sub points in the conversation ahead. Let’s take a step back, going bigger picture and expanding the time horizon. So why don’t you walk our listeners through your career journey? I mean, what have you been doing? How you got into the field of customer success and what led you to what you’re doing today?

Great. So I have to say, I always liked working with people and I always loved technology. So I can say my career journey kind of took a surprising twist throughout my career. But I did evolve a lot.

So I studied industrial engineering and a master degree in business. And for me, industrial engineering was perfect. It’s a kind of a broad degree that kind of gives you a little bit of everything, which is always something that I liked.

I like to spread out. And then I started with implementing SAP, the SAP ERP, if you’re familiar with customers. That gave me the background of working with customers, implementing software.

I think that was a really good first step in my career. From that, I did the big project management at Amdocs, which really gives you, it was probably a very good school for me, working in an enterprise organization, managing huge projects, many man-month. This is how we used to measure those projects.

And this is really the tool set to move forward. Then I did kind of a twist. I felt I needed to increase my technological knowledge.

I’m a very big believer that you need to build a very good technical foundation. Even if you move and you change your career later on, I think the foundation needs to be technical, at least for me, that’s something which is… I like understanding the technology. I did a few good years in ClickView.

Now it’s called Click, but I learned behind how to model data sets and build dashboards, which I have to say, it’s probably the best I did in my career. Data is something that people always need to understand how to work with data, how to present, how to tell a story with data. That’s something that you always need.

So even as an executive today, I always find myself telling a story using data, building those presentations to our management. So I’m really happy I took that decision back in the days. After that, I moved to Sisense.

It used to be a startup competing with Tableau and Click as well. I started off as a BI consultant. And back in those days, the whole customer success motion started to really grow.

And I was offered with the opportunity to actually move from the technical team to the account management team, as you were building and transitioning it to customer success with all customer success practices. And this is where I knew I need to do this shift. So I already gained enough technical background.

And I said, this is it. Now I’m going to jump into the business side of things. The advantage that I have, being the one that worked with the tool and really understands how it works.

And let me just pause, interrupt you over there, right? So when you were at Sisense, and this was about 10 years ago or so, and you’re right, I mean, you correctly pointed out, this was when this whole customer success movement started gaining traction. Thanks to Nick Meta, Gainsight, other products specifically geared towards the customer success professionals. I think that was a big inflection point, if you will.

So from your time at Sisense and even prior, if you can walk us through how customer success was there formally or informally, and then how it became more formal after that.

Yeah. So I have to say, first of all, it’s a never ending journey.

I can’t say there’s one point it was A, and then we shifted to B. But back then when I started and joined the account management team, it was an account management team. Very reactive, very focused on taking a question from a customer when they want to expand, sending the quote, trying to find those opportunities, and less focused about being proactive and customer journey, making sure that we build the right partnership and really showcasing value and driving the partnership and product implementation forward. And actually joining that team and being there as we build everything from scratch.

So we built what today is pretty common, but back then it didn’t exist. We’ve designed the entire customer journey what happens after kickoff? Who should be there? What should we present? How do we align on the strategy? What do you ask? Who are the people that we need to talk to? Who’s the decision maker? W ho is the champion? How do you map those contacts in your CRM? Of course, by the way, if someone is curious. And then how onboarding should look like? Who is doing the onboarding? Where are we charging for that? Are we giving that for free? How many hours should we… When are we starting to charge for that? How do we end the onboarding? What are the onboarding goals? And then later on, as customers finish the onboarding, how many times do we engage with a customer throughout the year? We divided the customers into tiers as it’s a practice.

It’s a common practice today to segment your customer base. How do you find accounts with potential? How do you do the QBRs? When are you engaging for the renewal calls? And then we obviously expanded as the company grew and we built professional services packages and additional services and workshop. The bigger your customer gets, the thicker the services and the processes around us get, the more complex projects that you get.

Customer success, by the way, it’s definitely not just customer success managers. And I have to stress that. Customer success, I see it as an organization.

It’s customer success managers, it’s support, it’s professional services, it’s the engineers that are working with you. So, and it takes a different flavor in each organization. And it’s on us as leaders to craft this balance between the different team, not necessarily you need all of them in every company.

So it depends. And that’s the beauty of it. So there are playbooks and there are processes, but taking that and building that to a specific organization, that’s the art.

Yeah, yeah. That’s a great point, especially the last one that you mentioned, Alon, which is customizing. I mean, the playbooks, there are different sub-functions, even within a customer success, which you correctly said, right? Professional services, TAM support and so on, and engineers and CSMs.

But then how do you customize it to a specific point in time for the product maturity is one thing. The company maturity, the competition, which is the external angle, and also the market opportunity. It’s all of these things combined.

And that’s how I also map this whole go-to-market. So for me, go-to-market is never static. It’s ongoing, it’s iterative.

You need to keep updating it and customizing. And I’m hearing the same thing applies for customer success function as well.

Yeah, so definitely you start and that’s definitely tied to the status of the company. As a small startup, you start getting these customers, you’re doing everything manual. The bigger you get, you’re building the processes, you’re building the automations. Once you’re starting to get the enterprise accounts, this is also where, that’s a big leap forward as well.

Enterprise accounts, that’s a different motion. You need to have a team, you need to have the processes around it. You need to have the data as well.

But if you have one, it’s different than you have 10s of those types of customers.

And when you say enterprise account, how do you define enterprise account? Because even that definition varies.

You’re right, by the way.

So one, obviously I would look on the size of organization that you work with. So everything above the 1,000, 2,000 employees, usually those companies has different needs, different expectation, different processes, by the way, things longer. You have security restrictions, compliance that you need to be aware of as well.

They have their timelines, their rollouts. It’s harder to do things faster sometimes. And they also pay a bigger bill.

So their demands are bigger and they have bigger expectation, which is pretty understandable. And you have to accommodate that. It’s not just one man show from our side, usually.

You have to build a team in order to successfully roll out a solution. You need to have project managers. Sometimes those companies, they have expectation for a certain level of service as well.

You have to be ready for that a lot.

Yeah, fairness. I know I interrupted you.

Let’s go back to the original track, which is your journey. And you’re talking about your time at Sisense. And then what happens since Sisense and the transition?

At Sisense, I led the department of customer success team. I, by the way, also fulfilled one of my dreams, which was to try and be a product manager for over years. It was always a kind of dream of mine. And I have to say, I liked it a lot.

I learned a lot about sprints and how to design and how to plan ahead your year, your quarter so much. But for me, it’s customer success. At the end of the day, I realized that I love creating impact.

I think customer success is one of those unique roles that you can create impact almost every single day. Because you’re in the heart of the business, you’re this glue between customers and product and R&D and sales and the feedback that you can give. You can influence the product a lot if you build a great partnership with product, right? You can influence a lot.

And the impact that you can do on your customers daily, that’s priceless. So that’s I learned a lot. But then I came back to customer success.

I worked at two more startups. Since then, I scaled the customer success team. I built them from scratch.

I joined the check in almost the last three years. Also building the international customer success team and pre-sales team. The international team.

And in the last year, I’ve been VP customer success at Atera with a very unique opportunity, at least for me, a career-wise. Atera, it’s an interesting story because the company actually shifts from a PLG motion to an SLG motion. So what drew me to Atera is actually rebuilding the customers.

So when I joined, I already had a big team here, but it’s all geared towards PLG. And taking such a team and redesigning it to cater mid-size enterprise accounts, that’s building from scratch. And I’m a builder eventually.

And I really enjoy what I do. And this is probably the most exciting challenge I am doing this day. So that’s a lot of fun.

Yeah, I mean, that transition from PLG to laying sales in addition to PLG. I mean, assuming you guys kept PLG, but you’re laying, adding sales on top. That’s a pretty complex journey in itself, right? In fact, I remember at my time at the co-site a couple of years ago, where I was an interim product led growth leader over there.

So we were in that transition from inside sales, pure inside sales to PLG, and then PLG and laying over sales. That transition is complex.

And you kept them in parallel?

Yeah, that was the intent, at least at the PLG and doing sales over.

But of course it takes time, right? I mean, even getting a new go-to-market motion like PLG takes a year at least, because it involves rewiring the internal functional teams that data product team and so on. It involves the growth team that has to come in place. And then there’s a key element, which I kept emphasizing as my time over there, which is for PLG, when you’re in the product led growth motion, before your account or your users actually decide to become a customer, decide to open the wallets and pay, there should be a layer which is not sales, but very customer success-like.

So that’s a key emphasis that I made over there. So your thoughts on how you’re dealing with that in your current role, or how did you handle those challenges?

 So it’s definitely a challenge besides changing how people think and operate within the customer success. We, by the way, we’ve built two organizations, one for the PLG motion and one for the SLG one.

But I think there is a very, actually, I think we’re lucky to have these two motion. I’m a very big believer that the product should also excel, the product itself. And value and ease of use should be part of the product.

There’s a limit to what a CSM or customer success can do. It’s another service you can give to thousands of customers. And being in a company that has those two motions, it should be a synergy.

So the capabilities and the tools that we build for PLG, we can use that in SLG. Obviously, it has to come with a strategy and how do we apply those communications and product tutorials and all the materials that we create for PLGs. Even SLG and even enterprise accounts, they have end users.

And reaching out to those end users, that’s something a CSM would never have time to do. And that’s, I think, would be the breakthrough. It’s also, if we’re talking about how AI eventually is affecting departments, I see it also affects customer success and especially the PLG and communication with also with the SLG users.

So I see it kind of being brought together as we evolve as a company, not just us. I think in the future, it’s all best practices. How do you scale methods with high-touch accounts as well?

Yeah, I don’t know.

We’ll get more into the nuances. We kept that at a very high level. So let’s actually get into more of the tactical stuff also.

And let’s do that in the context of a go-to-market success story and a go-to-market pivot story. I’ll let you choose what you want to lead with, Alon. But if you can share one of each, that’d be good.

So let’s talk about a success story. Let’s start. So I think I would kind of share a recent example that I had, actually.

And for us, it’s very tied to onboarding or if I need to even to be more accurate, it’s something that we call re-onboarding. So as we grew from PLG, we did do onboarding, but not as, let’s say, the best way possible. So as I joined, we also redesigned how onboarding should look like.

We mapped the critical features, critical steps, and what makes a successful onboarding and what are those sticky features, what are our best and strongest features that eventually bring the most value to customers. We map that and we basically define how onboarding should look like.

Yeah, so what is onboarding like before? You started this initiative like from a metrics point of view, and why you as a leader and a leadership team decided to go down this path?

So it was more like a training. Onboarding was a product overview, confined for three months. You go through the product training and you’re done. We basically redefined that.

We changed. We have now onboarding goals. We have success criteria as we have targets.

And we align that with customers as well from day one. Nice. And we track this checklist and you can’t finish onboarding before you finish the goals that we’ve set.

But as part of this process as well, we actually realized that we have so many customers that supposedly finished the onboarding.

Onboarding. But they’re not successful yet.

Yeah, exactly. And we actually started this initiative. We call it re-onboarding and we call it a Delta Force and started re-onboarding.

Approaching them proactively, offering to do health checks and re-evaluation of the implementation to kind of catch up and see if there’s any projects that we missed. And that created a really big impact. And today it’s actually a service that we do as part of the journey.

So the post onboarding and for customers that are with us for a while, we’re doing this health check and helping our customers to kind of revamp their implementation and see if there’s additional value, additional features that we released during this time that we can help them out. So that’s a big success story for us.

So what were the metrics? Like how were you measuring impact both internally for you guys as well as for the customers themselves?

So actually that’s an easy one. It’s renewal rates. And we see the impact and we actually improved our renewal rates dramatically over the past year.

Got it. And how long was this initiative or the program? How long did it take to even corral the team, identify what needs to be done? How will you measure change the beta customers? And yeah, walk us through that process as well.

So evaluating, or at least defining onboarding took us, I would say around a month.

Okay.

And then launching it wasn’t that slow. We just, we took our best person back then.

The most technical one, he started running those re-onboarding, and now it’s a team of four people. So I would say executing that too pretty fast. But since then we took, let’s say around four months to increase this team that is doing these onboarding, re-onboarding.

Got it. And you guys have like a target or quota of X number of customers onboarded per month or per quarter?

Yeah. So we actually have a number of open slots of onboardings that we can and want to handle.

And we’re prioritizing that. So our CSM directors and team leads, they know how many accounts they can add each quarter in each month. And we need to prioritize them with the hope that eventually this number is also decreases because while we’re doing these projects, the new onboarding is also running in parallel.

So that should stabilize. By the way, you also asked me about metrics. So renewal rates are great, but that’s the end results.

Another metric that we’re building is also adoption scoring. And that’s a tricky one. The way we do it today is we actually look on a few parameters of key features in the product and try to assess how well the customers are using the product.

It’s not easy. It varies between size of the organization, the type of customer, the industry. We have quite a broad scope of customers’ sizes and shapes and industries.

So we do it subjectively. But we also, we’re actually using, we’re doing a few POCs with AI tools eventually to try and build this score in a better way. But that’s kind of the holy grail I’m hoping to get to in the coming months.

Nice. Yeah. And then, so you said adoption, which is key.

You guys started measuring that. Your team started measuring that. And after that, obviously translated to the trading indicator, the KPI, which is renewals.

So your renewals went up by what? X percentage? Like, can you give like just a percentage?

Double D. I can’t say exactly, but yeah.

And over what? A period of six months or 12 months?

Within, let’s say two quarters. Yeah. Six months.

Very cool. Well, that’s great.

I mean, that’s definitely the key, right? How I see it, Alon is, I mean, from an external perspective, all these are like table stakes. To your credit, when you came on board and you noticed that onboarding was defined as training, but that really didn’t translate into customers really being successful. Yeah.

I mean, we all know how training goes. I mean, sure, everyone is excited that you signed up for training. And especially if it’s like one, two, three, four, five days of training, by the end of day one or even day two, you’re tired, you’re exhausted.

People are going to trainings and imagine people, your customers, the users actually taking the learnings and looking to apply. That’s a huge gap.

Yeah.

And it’s also different between the customer to customer. And by the way, I don’t, training as a, as itself can be easily replaced with in-product tutorials or documentation or academies. Although I’m not the biggest fan of documentation and KBs.

I think people less and less are eager or excited to see those. I actually think it’s also needs to move as much as possible to be within the product. But trying to take the essence of the onboarding is, it’s more about consultancy.

Understanding what the customer is trying to achieve and help them implement that in the product. We have a goal, each onboarding, depending on the size of the account and the product that were purchased to reach an X amount of successful use cases. So, and that’s different than training, just going over the product, but that doesn’t mean anything if nothing is being used or implemented in the right way.

So great story. Congratulations to you and the team on that. So going to the second, which is like a go-to-market failure, but I wouldn’t really call it a failure.

It’s more like a pivot story. So if you can share that, let’s go with that as well, Alon.

I think it’s more of a pivot that took me a while, also within Atera to change the perception of customer success within the company, which wasn’t easy, by the way.

Being born in the PLG motion, the way the customer success organization was being looked at as the call makers or email vendors. And every time there was an initiative, there’s a webinar that we’re doing or an event or we need case studies. Let’s have the CSM startup project start picking up the phones and sending out emails.

They’ve been used as a call center, if I need to illustrate how that works.

And I can imagine all those requests coming mainly from marketing team, especially for case studies.

Yes, always. And it still happens from time to time when there’s an initiative or a change we need to implement. And then let’s have the CSMs to reach out all the customers and ask them X.

And within the SLG motion or the high touch motion, we can’t do it.

When a CSM approaches a customer, it has to be very accurate. It can be automated emails. It can be generated.

We can’t approach them every week with a different method to our marketing campaign. This is not why we’re here for. It’s abusing our name, our reputation and the connection that we’re trying to build.

With a customer, we have to use this carefully. And there’s other ways and methods to reach out customers. So that’s a pivot we needed to change.

It took a while, but happily we succeeded to do that as well. 

So how did you, so actually let’s double click. That’s a very important transition that you made there.

First is what was it within you that didn’t sit well? There is that personal pain or angst or anger that you would have felt for sure. That’s one thing. Second is, how did you bring about that change and how did it influence the other teams?

So first, being a CSM in the past, you know how painful it is to get a customer to reply.

They have thousands, not thousands, they have tens of vendors. Everybody’s trying to get their attentions and they have BDRs. You have to position yourself as the expert.

For someone, myself, I barely have time to read emails. If my contact, a vendor that I’m using, will send me an email every week about something, I would stop opening his emails. Because I know it’s automatic.

I know it’s generated. And again, I’m separating between PLG and high-touch accounts. So it was very clear for me, for someone who’s managing customer success, it’s easy.

For other people in an organization, it’s not necessarily something they even think about. You’re coming from marketing or sales and you’re thinking about a pipeline. Even within sales, you have the BDRs that generate the leads.

You look at things as a pipeline. And for high-touch customer success, it’s different. It’s the last thing you think about it about customer success to be a pipeline.

And I needed to do some convincing. So it wasn’t just about why not. It’s also presenting alternatives.

And there are alternatives you can do. We can send those emails for marketing into in-product campaigns as well. And we shifted that.

And we’re trying to keep those CSMs for the things that matter and also to do planning ahead of time. So we know if there’s an important initiative, we would start pushing the efforts within the QPRs, within the meetings that we have, and not sending an email a few days before. And that’s a shift we needed to make.

Got it. Okay. So obviously you had to have some tough conversations with the marketing counterpart, marketing leadership, and possibly even sales leadership and product leadership, I would assume.

Yeah. Again, I don’t see it’s tough. At the end of the day, it’s our job.

It’s about building a case. It’s convincing. So when you present the data, when you present a plan, then it should work.

Again, it makes sense. Everyone. Of course, while we are reaching the goals and we’re getting the customers to where we want them.

Yeah. So going back to the storyline, so that’s the pivot that you had to change the culture and the perception of customer success within the company. And how did you really measure? I don’t know if there’s a way to measure or was it just anecdotal where people started approaching you and your team from a different angle? 

It’s anecdotal, but it’s actually a KPI that I used to measure in my past companies.

I haven’t introduced it here, which I might do in the future. But CSMs usually they have their targets as well. And those targets usually are broken into several KPIs.

This is a KPI. I like to call it advocacy. And usually advocacy is kind of, it could be a mixture of a few initiatives. How many case studies are you able to bring? References for sales appear in an event your company in doing it, et cetera.

And actually, I really like this KPI because I think a CSM that was A, able to drive adoption and make their customers successful and B, also build a good relationship that he’s able to ask the customer for this favor. And you succeeded in both. So he should be good in generating those advocacy tasks as well.

I’m so glad that you brought up advocacy because one of the things that I look at and which are real clear indicators of a good and happy customer base is advocacy. We can talk about onboarding. We can talk about adoption.

We can talk about renewals and then NRR at the end of the day, all of these bubbling to NRR. But then how many advocates are there within your customer base who are willing to vouch for you and your team and your product? That’s a real important KPI.

I totally agree.

By the way, that’s something a company should manage. If you really want to build a good pipeline, you need to manage that. You need to make sure that you don’t abuse your customers as well and also make it work for them.

There’s advocacy programs that you can build and it’s definitely something a company should see how she’s focused on it and build this process. 

So for me, throughout my conversations across different spectrums of people that include founders as well as the go-to-market practitioners. So I also am very closely engaged with founders, like early stage founders and even founders who are at 5 million, 10 million.

So one thing that I noticed, Alon, is founders, they know the value of advocacy. That’s crucial, especially in the early stages of company building. You need to have reference and advocacy.

That’s a clear growth engine. But somewhere along the line, as the company grows from 1 million to 5 million, 10, 50 and so on, that essence gets diluted.

 And that’s understandable because you transition from keeping those handful of advocators that have been with you from day one, in your design partners, it was easy for you to build a very strong relationships because you’re the CEO, you’re the founder.

It was easy to ask for a favor. And by the way, those people as early adopters, they probably, they like it also. So I would always have, if I love the product I’m using, I would love to assist, especially if I was so early in the stage and I helped shaping it.

And I believe product. But as you grow, they don’t have this close relationship. The customer management is transitioned to the customer success team and you have to manage it.

It’s all about scaling. And I talked before about execution. This is exactly it.

This is execution. You’re chopping a grade. You need to mark your candidates, your advocators in your CRM.

I need to make sure that you don’t abuse them. You need to make sure that you’re working to create those advocates. And it has to worthwhile also for the CSMs.

Because it’s asking a favor from a customer. So your CSMs also have to being compensated or it has to be part of their targets or some sort of an initiative or incentive for them to build that. So you have to keep that in mind as well.

Absolutely. Great point. So throughout your customer success journey, I mean, you started off from a SAP implementation role and then you moved into TAM and then eventually customer success.

You moved to product management briefly, but again, back to customer success. So in this entire journey of yours, Alon, what almost broke you down or broke you in this journey? 

Well, I’m a person that it’s hard for me to be broken, I have to say. I think the toughest for me in back in my career, or just a few stages back, was when I was in a small startup that didn’t grow.

So I actually joined a small startup right before they were supposed to raise their first big round and joined to build the team. And I came with such big plans and we need the head of support and we need the team of, sorry, onboarding manager, and we need the CSM, et cetera. But the funding didn’t came.

And it’s hard because you’re coming for a specific role and it doesn’t happen. And I’m not a person that gives up so easily, but eventually after almost a year, you realize that this is not what you’re assigned for. So you have to take the right decision what is best for you as well.

So I think it was just one of the hardest decision I had to take. But I think at the end of the day, it’s a decision everyone has to take in their career as well and do what’s right. 

What are the learnings or insights that came to you from that journey?

Wow, a lot.

There’s the way I choose the next, at least my companies that I work for. I think I learned a lot from that. The size of the organization, the funding that they have, how I look about the product and how they generate revenue, by the way.

Is it from services? Is it a reoccurring error from licenses? So there’s a lot of metrics that I know how to look on today, which I didn’t know 10 years ago. 

I know we’re coming up against the time over here. So last couple of questions for you, Alon.

Sure. 

One is like, what is really maybe a trend or something within the customer success space that’s really caught your attention that you’re really curious about and you want to go down that path? 

It’s an easy one. And I have to say, yeah.

And I know everyone is obsessed about that. And I really try to look at it, not as the hype motion, yeah, AI is going to replace everyone in the next. I’m not really a believer, especially, you know what, not in customer success and definitely not in the high touch motion of customer success.

But for me, honestly, I think I’m grateful that I’m in this position, that I can really do something new. So putting aside that I’m also rebuilding this team now at Eterra, if you’re now a leader of customer success, it’s a rare opportunity to do something that nobody has done before.

And even in, I have to say, in customer success, it’s even harder. There are certain departments within the go-to market motion that there’s already best practices and there’s an abundant of tools that are already being used. In customer success, it’s just starting.

And you don’t have these playbooks yet. And you don’t have the products yet that I envisioned. And reshaping and thinking how customer success is going to be transformed in the next few years, that’s a huge opportunity.

And I’m grateful also that my company understand that. And I’m giving the mandate to design and operate in order to achieve this transformation. Obviously, we have our goals as well.

You want to be efficient and you want to scale in an efficient way. But I truly believe this is the point where customer success is about to transform and have their next big shift. If customer success was born with the SaaS motion, this is the next job.

And I talked before a little bit about communicating better with end users. I have to say, this is where I think we were able to make a dramatic change. Because we, in high touch still, you don’t have time to reach end users.

And AI could help us understand data better, building customer success plans better, and creating plans. I see it in a way that it will be a hybrid between high touch and scale and allowing high touch CSM being able to execute their strategies and reach eventually in a personalized way to the end users as well and driving adoption. And we all know how adoption is important.

And adoption obviously leads to growth and retention and et cetera. 

Yeah, fantastic.Great point.

I mean, I love the fact how you actually double clicked on what really mean by AI and customer success. And there’s so many nuances in there. So yeah, I look forward to hearing more from your team and from you downstream in how you’re bringing and incorporating AI in customer success.

So final question for you, Helen, is if you were to turn back the clock and you could go to day one of your go-to-market journey, what advice would you give to your younger self? 

Be patient. I’m a very eager and competitive person. And when you started, at least when I started the career, you’re always thinking, okay, what’s next? How am I going to develop myself? How am I going to get to the next bigger role? And it’s really a journey.

I think every role that I did, I learned. And to be good at what you do, I don’t believe in jumping from a junior role to a very senior role. The mileage that I did, I learned so much.

The complex projects that I had, the scenarios. Dealing with all of that is what brought me to what I am today. So, but back then, you know, you’re not sure.

Will I able to make the next jumps? When will I’ll do it? So it’s being patient and just tell myself you’re on the right path. Maybe buy some stock options of VBR or Bitcoin back then, but that’s a whole different story. Yeah.

Very good. Yeah. That’s a great point to end on.

Be patient. And yeah, growth and success will eventually come in your journey. So thank you so much for your time, Alon.

I enjoyed the conversation, especially the fact that you are the first customer success leader in the podcast. I personally learned so much and I’m sure the listeners who are especially focusing on customer success would enjoy and value this conversation as well. So thank you for that.

Thank you, Vijay. It’s a great honor to be here. I’m a big fan and thank you so much.

In this episode of the B2B Go-To-Market Leaders Podcast, Vijay Damojipurapu sits down with Alon Ahronberg, VP of Customer Success at Atera, to explore how customer success drives sustainable revenue and long-term retention in modern B2B companies.

From his early career in engineering and BI consulting to leading customer success at global SaaS startups, Alon shares lessons from scaling teams, building onboarding frameworks, and transforming a PLG motion into a hybrid sales-led growth (SLG) strategy.

Together, they unpack:

• How to define go-to-market holistically across product, sales, marketing, and customer success.
• The critical role of onboarding and re-onboarding in improving renewal rates and product adoption.
• Why internal collaboration between CSMs, marketing, and sales determines customer lifetime value.
• The cultural shift needed to elevate customer success from “call center” to strategic growth partner.
• How AI will reshape customer success, bridging high-touch strategy with scalable automation.

Whether you’re a founder, go-to-market leader, or customer success professional, this episode offers a masterclass on aligning post-sale execution with growth.

Connect with Alon Ahronberg on LinkedIn

Connect with Vijay Damojipurapu on LinkedIn

Listen To The Episode:

The Hybrid GTM Playbook: Turning Customer Success into a Growth Engine

I’ll again start off with my signature question, which is how do you view and define go-to-market?

So I love it when you ask this question. And honestly, I look at it first as a holistic strategy that kind of unites together product, marketing, sales, and of course, customer success. In a way that ensures we eventually our solutions, our products that we build reaches the right audience and is able to generate value and business outcomes to our clients.

Now, I said strategy. I think also execution is a very big part of that as well. You got to have both. So strategy and execution. And coming from customer success, I have to add the customer’s success angle of this topic.

I would also say there’s kind of four points. I look at it from my perspective. One, as customer success, we need to understand the messaging. Are customers here throughout the marketing funnel, during sales? What are the expectations from the products that they purchase from us? The second and probably one of the most important points is aligning the onboarding as well. What happens after the sales, that’s on us. And that has to be executed the best way possible.

It’s so easy to miss that critical point. We have to deliver value fast. And to do that, you need to understand their expectations. What are they coming to get from your product? In order to deliver the best onboarding experience and obviously to get live and get value from the product as soon as you can. The third point is building the collaboration. So I said the kind of the four main teams that are involved, but you have to build a very good collaboration. It never stops. And companies that succeed have this good collaboration. We don’t work in silos.

And the fourth point is crafting this journey. Customer success also, we don’t operate in a vacuum. So we need to understand the entire journey.How does the company land the customer in? How do we build the onboarding, the adoption? How do we build the expansion, the upselling motion together with sales? And obviously the renewal. So it’s a never ending journey. We still need marketing throughout this cycle.

We need sales, account management. We have to think about this process as well. So that’s my kind of summary of GTM and this is how I look at it.

Yeah, love it. In fact, I’m so glad that we now have a customer success angle and lens to this, which was missing from the show until now. So that’s bad on me, but I’m going to fix it going forward.

The reason why I say I love to have a customer success angle, which you articulated so well, I believe in your points, two, three, and four, especially, right? The first one, pretty much everyone on the show talk about customer problem and building a product that solves the customer problems. I get it. Everyone gets it.

I think that’s a prerequisite. But what’s not been emphasized so far on this show are the points number two, three, and four. Points two around onboarding.

So successful onboarding is critical. That’s one for sure. The next is a collaboration.

I mean, when you said collaboration, I was thinking external, which is customer success and the customers, but you also emphasized collaboration internally, especially with sales and product and not so much on marketing, but I understand where you’re coming from. And the fourth angle is thinking about the success of the customer, but at the same time, how you as a team, all of you can increase and should increase the adoption, which will translate to upsell, renewal, and so on.

That’s the base. And then when I said collaboration, internal collaboration, that’s where sometimes company miss. So obviously our job is to collaborate with customer. That’s the essence of customer success.

But again, you have to build this partnership within the company as well. Good leaders, they don’t forget. This is what needs to be done as well.

It’s not everything is on us. Not everything is customer success, churn and renewal problems and expansion. That’s a company goal. We are blue that kind of stick everything together.

And something that I’ve started noticing and I’ve been getting validation when I speak to other go-to-market leaders and even from an exit is to the detriment of the company’s growth and even to the detriment of customer being valued. I see a lot of emphasis within the B2B go-to-market motion.

I mean, a lot of emphasis is being placed on new logo acquisition, not so much on your existing customer base. Your thoughts on that, Alon?

You’re so right. I have to say, I see this shifting and I see more and more understanding this.

It used to be the situation a few years ago. I do see it shifts and change. There’s a big realization that your existing revenue can generate much more.

And I see more teams of account management and more collaboration between customer success and sales. But I think that’s probably the biggest drivers for revenue as well. Again, it also depends on the size of the company and its status.

Obviously for startups, you have to drive for new revenue to come in as well. But generating revenue from your existing customer base, by the way, in my view, it’s not just for the revenue sake. If your customers are not growing, there’s a good chance they won’t renew.

So successful customers, they use your product, they need more and more features, more licenses. You want to see, you have to build this growth as well. I do see this shift.

I think it’s there. The understanding is already happening. Where there’s always a struggle or a dilemma is who’s driving the upsell or the expansion motion.

Is it the customer success managers? Is it on the account executives? Do you have to build an account management team? So that’s a question, by the way. And by the way, I don’t think there’s a silver bullet to this question as well. It depends on the state of your company, how big the company is, where you are in your journey, how complex your product.

Wait, if your product is very technical, you want your CSMs to be technical as well. And at the end of the day, I see customer success, or at least the customer success managers role as a consultant, someone who brings value to the table. And to do that, you have to understand the product well enough and be able to advise.

And if you’re able to build this balance between consulting and pushing for the expansion eventually, then you’re succeeding. It’s something breaking those two apart, build a good partnership between a CSM or AM or account executives, then it works really well.

Now that’s a great point you mentioned, Alon, which is for a customer to be successful, the CS team has to act as trusted advisors. And that starts with having a good knowledge around the product and helping them get onboarded successfully and improve the adoption internally. I know we can go down this rabbit hole more.

I just add, I think definitely the CSMs are in the best position to identify potential. They know their customers best, they’re able to advise, they know to find those opportunities, whether if they’re eventually doing the commercial negotiation, that’s a different topic. But they have to have this mindset of looking for growth. They have to.

Excellent. All right. I’m sure we’ll get into a lot of those topics and sub points in the conversation ahead. Let’s take a step back, going bigger picture and expanding the time horizon. So why don’t you walk our listeners through your career journey? I mean, what have you been doing? How you got into the field of customer success and what led you to what you’re doing today?

 Great. So I have to say, I always liked working with people and I always loved technology. So I can say my career journey kind of took a surprising twist throughout my career. But I did evolve a lot.

So I studied industrial engineering and a master degree in business. And for me, industrial engineering was perfect. It’s a kind of a broad degree that kind of gives you a little bit of everything, which is always something that I liked.

I like to spread out. And then I started with implementing SAP, the SAP ERP, if you’re familiar with customers. That gave me the background of working with customers, implementing software.

I think that was a really good first step in my career. From that, I did the big project management at Amdocs, which really gives you, it was probably a very good school for me, working in an enterprise organization, managing huge projects, many man-month. This is how we used to measure those projects.

And this is really the tool set to move forward. Then I did kind of a twist. I felt I needed to increase my technological knowledge.

I’m a very big believer that you need to build a very good technical foundation. Even if you move and you change your career later on, I think the foundation needs to be technical, at least for me, that’s something which is… I like understanding the technology. I did a few good years in ClickView.

Now it’s called Click, but I learned behind how to model data sets and build dashboards, which I have to say, it’s probably the best I did in my career. Data is something that people always need to understand how to work with data, how to present, how to tell a story with data. That’s something that you always need.

So even as an executive today, I always find myself telling a story using data, building those presentations to our management. So I’m really happy I took that decision back in the days. After that, I moved to Sisense.

It used to be a startup competing with Tableau and Click as well. I started off as a BI consultant. And back in those days, the whole customer success motion started to really grow.

And I was offered with the opportunity to actually move from the technical team to the account management team, as you were building and transitioning it to customer success with all customer success practices. And this is where I knew I need to do this shift. So I already gained enough technical background.

And I said, this is it. Now I’m going to jump into the business side of things. The advantage that I have, being the one that worked with the tool and really understands how it works.

And let me just pause, interrupt you over there, right? So when you were at Sisense, and this was about 10 years ago or so, and you’re right, I mean, you correctly pointed out, this was when this whole customer success movement started gaining traction. Thanks to Nick Meta, Gainsight, other products specifically geared towards the customer success professionals. I think that was a big inflection point, if you will.

So from your time at Sisense and even prior, if you can walk us through how customer success was there formally or informally, and then how it became more formal after that.

Yeah. So I have to say, first of all, it’s a never ending journey.

I can’t say there’s one point it was A, and then we shifted to B. But back then when I started and joined the account management team, it was an account management team. Very reactive, very focused on taking a question from a customer when they want to expand, sending the quote, trying to find those opportunities, and less focused about being proactive and customer journey, making sure that we build the right partnership and really showcasing value and driving the partnership and product implementation forward. And actually joining that team and being there as we build everything from scratch.

So we built what today is pretty common, but back then it didn’t exist. We’ve designed the entire customer journey what happens after kickoff? Who should be there? What should we present? How do we align on the strategy? What do you ask? Who are the people that we need to talk to? Who’s the decision maker? W ho is the champion? How do you map those contacts in your CRM? Of course, by the way, if someone is curious. And then how onboarding should look like? Who is doing the onboarding? Where are we charging for that? Are we giving that for free? How many hours should we… When are we starting to charge for that? How do we end the onboarding? What are the onboarding goals? And then later on, as customers finish the onboarding, how many times do we engage with a customer throughout the year? We divided the customers into tiers as it’s a practice.

It’s a common practice today to segment your customer base. How do you find accounts with potential? How do you do the QBRs? When are you engaging for the renewal calls? And then we obviously expanded as the company grew and we built professional services packages and additional services and workshop. The bigger your customer gets, the thicker the services and the processes around us get, the more complex projects that you get.

Customer success, by the way, it’s definitely not just customer success managers. And I have to stress that. Customer success, I see it as an organization.

It’s customer success managers, it’s support, it’s professional services, it’s the engineers that are working with you. So, and it takes a different flavor in each organization. And it’s on us as leaders to craft this balance between the different team, not necessarily you need all of them in every company.

So it depends. And that’s the beauty of it. So there are playbooks and there are processes, but taking that and building that to a specific organization, that’s the art.

Yeah, yeah. That’s a great point, especially the last one that you mentioned, Alon, which is customizing. I mean, the playbooks, there are different sub-functions, even within a customer success, which you correctly said, right? Professional services, TAM support and so on, and engineers and CSMs.

But then how do you customize it to a specific point in time for the product maturity is one thing. The company maturity, the competition, which is the external angle, and also the market opportunity. It’s all of these things combined.

And that’s how I also map this whole go-to-market. So for me, go-to-market is never static. It’s ongoing, it’s iterative.

You need to keep updating it and customizing. And I’m hearing the same thing applies for customer success function as well.

Yeah, so definitely you start and that’s definitely tied to the status of the company. As a small startup, you start getting these customers, you’re doing everything manual. The bigger you get, you’re building the processes, you’re building the automations. Once you’re starting to get the enterprise accounts, this is also where, that’s a big leap forward as well.

Enterprise accounts, that’s a different motion. You need to have a team, you need to have the processes around it. You need to have the data as well.

But if you have one, it’s different than you have 10s of those types of customers.

And when you say enterprise account, how do you define enterprise account? Because even that definition varies.

You’re right, by the way.

So one, obviously I would look on the size of organization that you work with. So everything above the 1,000, 2,000 employees, usually those companies has different needs, different expectation, different processes, by the way, things longer. You have security restrictions, compliance that you need to be aware of as well.

They have their timelines, their rollouts. It’s harder to do things faster sometimes. And they also pay a bigger bill.

So their demands are bigger and they have bigger expectation, which is pretty understandable. And you have to accommodate that. It’s not just one man show from our side, usually.

You have to build a team in order to successfully roll out a solution. You need to have project managers. Sometimes those companies, they have expectation for a certain level of service as well.

You have to be ready for that a lot.

Yeah, fairness. I know I interrupted you.

Let’s go back to the original track, which is your journey. And you’re talking about your time at Sisense. And then what happens since Sisense and the transition?

At Sisense, I led the department of customer success team. I, by the way, also fulfilled one of my dreams, which was to try and be a product manager for over years. It was always a kind of dream of mine. And I have to say, I liked it a lot.

I learned a lot about sprints and how to design and how to plan ahead your year, your quarter so much. But for me, it’s customer success. At the end of the day, I realized that I love creating impact.

I think customer success is one of those unique roles that you can create impact almost every single day. Because you’re in the heart of the business, you’re this glue between customers and product and R&D and sales and the feedback that you can give. You can influence the product a lot if you build a great partnership with product, right? You can influence a lot.

And the impact that you can do on your customers daily, that’s priceless. So that’s I learned a lot. But then I came back to customer success.

I worked at two more startups. Since then, I scaled the customer success team. I built them from scratch.

I joined the check in almost the last three years. Also building the international customer success team and pre-sales team. The international team.

And in the last year, I’ve been VP customer success at Atera with a very unique opportunity, at least for me, a career-wise. Atera, it’s an interesting story because the company actually shifts from a PLG motion to an SLG motion. So what drew me to Atera is actually rebuilding the customers.

So when I joined, I already had a big team here, but it’s all geared towards PLG. And taking such a team and redesigning it to cater mid-size enterprise accounts, that’s building from scratch. And I’m a builder eventually.

And I really enjoy what I do. And this is probably the most exciting challenge I am doing this day. So that’s a lot of fun.

Yeah, I mean, that transition from PLG to laying sales in addition to PLG. I mean, assuming you guys kept PLG, but you’re laying, adding sales on top. That’s a pretty complex journey in itself, right? In fact, I remember at my time at the co-site a couple of years ago, where I was an interim product led growth leader over there.

So we were in that transition from inside sales, pure inside sales to PLG, and then PLG and laying over sales. That transition is complex.

And you kept them in parallel?

Yeah, that was the intent, at least at the PLG and doing sales over.

But of course it takes time, right? I mean, even getting a new go-to-market motion like PLG takes a year at least, because it involves rewiring the internal functional teams that data product team and so on. It involves the growth team that has to come in place. And then there’s a key element, which I kept emphasizing as my time over there, which is for PLG, when you’re in the product led growth motion, before your account or your users actually decide to become a customer, decide to open the wallets and pay, there should be a layer which is not sales, but very customer success-like.

So that’s a key emphasis that I made over there. So your thoughts on how you’re dealing with that in your current role, or how did you handle those challenges?

 So it’s definitely a challenge besides changing how people think and operate within the customer success. We, by the way, we’ve built two organizations, one for the PLG motion and one for the SLG one.

But I think there is a very, actually, I think we’re lucky to have these two motion. I’m a very big believer that the product should also excel, the product itself. And value and ease of use should be part of the product.

There’s a limit to what a CSM or customer success can do. It’s another service you can give to thousands of customers. And being in a company that has those two motions, it should be a synergy.

So the capabilities and the tools that we build for PLG, we can use that in SLG. Obviously, it has to come with a strategy and how do we apply those communications and product tutorials and all the materials that we create for PLGs. Even SLG and even enterprise accounts, they have end users.

And reaching out to those end users, that’s something a CSM would never have time to do. And that’s, I think, would be the breakthrough. It’s also, if we’re talking about how AI eventually is affecting departments, I see it also affects customer success and especially the PLG and communication with also with the SLG users.

So I see it kind of being brought together as we evolve as a company, not just us. I think in the future, it’s all best practices. How do you scale methods with high-touch accounts as well?

Yeah, I don’t know.

We’ll get more into the nuances. We kept that at a very high level. So let’s actually get into more of the tactical stuff also.

And let’s do that in the context of a go-to-market success story and a go-to-market pivot story. I’ll let you choose what you want to lead with, Alon. But if you can share one of each, that’d be good.

So let’s talk about a success story. Let’s start. So I think I would kind of share a recent example that I had, actually.

And for us, it’s very tied to onboarding or if I need to even to be more accurate, it’s something that we call re-onboarding. So as we grew from PLG, we did do onboarding, but not as, let’s say, the best way possible. So as I joined, we also redesigned how onboarding should look like.

We mapped the critical features, critical steps, and what makes a successful onboarding and what are those sticky features, what are our best and strongest features that eventually bring the most value to customers. We map that and we basically define how onboarding should look like.

Yeah, so what is onboarding like before? You started this initiative like from a metrics point of view, and why you as a leader and a leadership team decided to go down this path?

So it was more like a training. Onboarding was a product overview, confined for three months. You go through the product training and you’re done. We basically redefined that.

We changed. We have now onboarding goals. We have success criteria as we have targets.

And we align that with customers as well from day one. Nice. And we track this checklist and you can’t finish onboarding before you finish the goals that we’ve set.

But as part of this process as well, we actually realized that we have so many customers that supposedly finished the onboarding.

Onboarding. But they’re not successful yet.

Yeah, exactly. And we actually started this initiative. We call it re-onboarding and we call it a Delta Force and started re-onboarding.

Approaching them proactively, offering to do health checks and re-evaluation of the implementation to kind of catch up and see if there’s any projects that we missed. And that created a really big impact. And today it’s actually a service that we do as part of the journey.

So the post onboarding and for customers that are with us for a while, we’re doing this health check and helping our customers to kind of revamp their implementation and see if there’s additional value, additional features that we released during this time that we can help them out. So that’s a big success story for us.

So what were the metrics? Like how were you measuring impact both internally for you guys as well as for the customers themselves?

So actually that’s an easy one. It’s renewal rates. And we see the impact and we actually improved our renewal rates dramatically over the past year.

Got it. And how long was this initiative or the program? How long did it take to even corral the team, identify what needs to be done? How will you measure change the beta customers? And yeah, walk us through that process as well.

So evaluating, or at least defining onboarding took us, I would say around a month.

Okay.

And then launching it wasn’t that slow. We just, we took our best person back then.

The most technical one, he started running those re-onboarding, and now it’s a team of four people. So I would say executing that too pretty fast. But since then we took, let’s say around four months to increase this team that is doing these onboarding, re-onboarding.

Got it. And you guys have like a target or quota of X number of customers onboarded per month or per quarter?

Yeah. So we actually have a number of open slots of onboardings that we can and want to handle.

And we’re prioritizing that. So our CSM directors and team leads, they know how many accounts they can add each quarter in each month. And we need to prioritize them with the hope that eventually this number is also decreases because while we’re doing these projects, the new onboarding is also running in parallel.

So that should stabilize. By the way, you also asked me about metrics. So renewal rates are great, but that’s the end results.

Another metric that we’re building is also adoption scoring. And that’s a tricky one. The way we do it today is we actually look on a few parameters of key features in the product and try to assess how well the customers are using the product.

It’s not easy. It varies between size of the organization, the type of customer, the industry. We have quite a broad scope of customers’ sizes and shapes and industries.

So we do it subjectively. But we also, we’re actually using, we’re doing a few POCs with AI tools eventually to try and build this score in a better way. But that’s kind of the holy grail I’m hoping to get to in the coming months.

Nice. Yeah. And then, so you said adoption, which is key.

You guys started measuring that. Your team started measuring that. And after that, obviously translated to the trading indicator, the KPI, which is renewals.

So your renewals went up by what? X percentage? Like, can you give like just a percentage?

Double D. I can’t say exactly, but yeah.

And over what? A period of six months or 12 months?

Within, let’s say two quarters. Yeah. Six months.

Very cool. Well, that’s great.

I mean, that’s definitely the key, right? How I see it, Alon is, I mean, from an external perspective, all these are like table stakes. To your credit, when you came on board and you noticed that onboarding was defined as training, but that really didn’t translate into customers really being successful. Yeah.

I mean, we all know how training goes. I mean, sure, everyone is excited that you signed up for training. And especially if it’s like one, two, three, four, five days of training, by the end of day one or even day two, you’re tired, you’re exhausted.

People are going to trainings and imagine people, your customers, the users actually taking the learnings and looking to apply. That’s a huge gap.

Yeah.

And it’s also different between the customer to customer. And by the way, I don’t, training as a, as itself can be easily replaced with in-product tutorials or documentation or academies. Although I’m not the biggest fan of documentation and KBs.

I think people less and less are eager or excited to see those. I actually think it’s also needs to move as much as possible to be within the product. But trying to take the essence of the onboarding is, it’s more about consultancy.

Understanding what the customer is trying to achieve and help them implement that in the product. We have a goal, each onboarding, depending on the size of the account and the product that were purchased to reach an X amount of successful use cases. So, and that’s different than training, just going over the product, but that doesn’t mean anything if nothing is being used or implemented in the right way.

So great story. Congratulations to you and the team on that. So going to the second, which is like a go-to-market failure, but I wouldn’t really call it a failure.

It’s more like a pivot story. So if you can share that, let’s go with that as well, Alon.

I think it’s more of a pivot that took me a while, also within Atera to change the perception of customer success within the company, which wasn’t easy, by the way.

Being born in the PLG motion, the way the customer success organization was being looked at as the call makers or email vendors. And every time there was an initiative, there’s a webinar that we’re doing or an event or we need case studies. Let’s have the CSM startup project start picking up the phones and sending out emails.

They’ve been used as a call center, if I need to illustrate how that works.

And I can imagine all those requests coming mainly from marketing team, especially for case studies.

Yes, always. And it still happens from time to time when there’s an initiative or a change we need to implement. And then let’s have the CSMs to reach out all the customers and ask them X.

And within the SLG motion or the high touch motion, we can’t do it.

When a CSM approaches a customer, it has to be very accurate. It can be automated emails. It can be generated.

We can’t approach them every week with a different method to our marketing campaign. This is not why we’re here for. It’s abusing our name, our reputation and the connection that we’re trying to build.

With a customer, we have to use this carefully. And there’s other ways and methods to reach out customers. So that’s a pivot we needed to change.

It took a while, but happily we succeeded to do that as well. 

So how did you, so actually let’s double click. That’s a very important transition that you made there.

First is what was it within you that didn’t sit well? There is that personal pain or angst or anger that you would have felt for sure. That’s one thing. Second is, how did you bring about that change and how did it influence the other teams?

So first, being a CSM in the past, you know how painful it is to get a customer to reply.

They have thousands, not thousands, they have tens of vendors. Everybody’s trying to get their attentions and they have BDRs. You have to position yourself as the expert.

For someone, myself, I barely have time to read emails. If my contact, a vendor that I’m using, will send me an email every week about something, I would stop opening his emails. Because I know it’s automatic.

I know it’s generated. And again, I’m separating between PLG and high-touch accounts. So it was very clear for me, for someone who’s managing customer success, it’s easy.

For other people in an organization, it’s not necessarily something they even think about. You’re coming from marketing or sales and you’re thinking about a pipeline. Even within sales, you have the BDRs that generate the leads.

You look at things as a pipeline. And for high-touch customer success, it’s different. It’s the last thing you think about it about customer success to be a pipeline.

And I needed to do some convincing. So it wasn’t just about why not. It’s also presenting alternatives.

And there are alternatives you can do. We can send those emails for marketing into in-product campaigns as well. And we shifted that.

And we’re trying to keep those CSMs for the things that matter and also to do planning ahead of time. So we know if there’s an important initiative, we would start pushing the efforts within the QPRs, within the meetings that we have, and not sending an email a few days before. And that’s a shift we needed to make.

Got it. Okay. So obviously you had to have some tough conversations with the marketing counterpart, marketing leadership, and possibly even sales leadership and product leadership, I would assume.

Yeah. Again, I don’t see it’s tough. At the end of the day, it’s our job.

It’s about building a case. It’s convincing. So when you present the data, when you present a plan, then it should work.

Again, it makes sense. Everyone. Of course, while we are reaching the goals and we’re getting the customers to where we want them.

Yeah. So going back to the storyline, so that’s the pivot that you had to change the culture and the perception of customer success within the company. And how did you really measure? I don’t know if there’s a way to measure or was it just anecdotal where people started approaching you and your team from a different angle? 

It’s anecdotal, but it’s actually a KPI that I used to measure in my past companies.

I haven’t introduced it here, which I might do in the future. But CSMs usually they have their targets as well. And those targets usually are broken into several KPIs.

This is a KPI. I like to call it advocacy. And usually advocacy is kind of, it could be a mixture of a few initiatives. How many case studies are you able to bring? References for sales appear in an event your company in doing it, et cetera.

And actually, I really like this KPI because I think a CSM that was A, able to drive adoption and make their customers successful and B, also build a good relationship that he’s able to ask the customer for this favor. And you succeeded in both. So he should be good in generating those advocacy tasks as well.

I’m so glad that you brought up advocacy because one of the things that I look at and which are real clear indicators of a good and happy customer base is advocacy. We can talk about onboarding. We can talk about adoption.

We can talk about renewals and then NRR at the end of the day, all of these bubbling to NRR. But then how many advocates are there within your customer base who are willing to vouch for you and your team and your product? That’s a real important KPI.

I totally agree.

By the way, that’s something a company should manage. If you really want to build a good pipeline, you need to manage that. You need to make sure that you don’t abuse your customers as well and also make it work for them.

There’s advocacy programs that you can build and it’s definitely something a company should see how she’s focused on it and build this process. 

So for me, throughout my conversations across different spectrums of people that include founders as well as the go-to-market practitioners. So I also am very closely engaged with founders, like early stage founders and even founders who are at 5 million, 10 million.

So one thing that I noticed, Alon, is founders, they know the value of advocacy. That’s crucial, especially in the early stages of company building. You need to have reference and advocacy.

That’s a clear growth engine. But somewhere along the line, as the company grows from 1 million to 5 million, 10, 50 and so on, that essence gets diluted.

 And that’s understandable because you transition from keeping those handful of advocators that have been with you from day one, in your design partners, it was easy for you to build a very strong relationships because you’re the CEO, you’re the founder.

It was easy to ask for a favor. And by the way, those people as early adopters, they probably, they like it also. So I would always have, if I love the product I’m using, I would love to assist, especially if I was so early in the stage and I helped shaping it.

And I believe product. But as you grow, they don’t have this close relationship. The customer management is transitioned to the customer success team and you have to manage it.

It’s all about scaling. And I talked before about execution. This is exactly it.

This is execution. You’re chopping a grade. You need to mark your candidates, your advocators in your CRM.

I need to make sure that you don’t abuse them. You need to make sure that you’re working to create those advocates. And it has to worthwhile also for the CSMs.

Because it’s asking a favor from a customer. So your CSMs also have to being compensated or it has to be part of their targets or some sort of an initiative or incentive for them to build that. So you have to keep that in mind as well.

Absolutely. Great point. So throughout your customer success journey, I mean, you started off from a SAP implementation role and then you moved into TAM and then eventually customer success.

You moved to product management briefly, but again, back to customer success. So in this entire journey of yours, Alon, what almost broke you down or broke you in this journey? 

Well, I’m a person that it’s hard for me to be broken, I have to say. I think the toughest for me in back in my career, or just a few stages back, was when I was in a small startup that didn’t grow.

So I actually joined a small startup right before they were supposed to raise their first big round and joined to build the team. And I came with such big plans and we need the head of support and we need the team of, sorry, onboarding manager, and we need the CSM, et cetera. But the funding didn’t came.

And it’s hard because you’re coming for a specific role and it doesn’t happen. And I’m not a person that gives up so easily, but eventually after almost a year, you realize that this is not what you’re assigned for. So you have to take the right decision what is best for you as well.

So I think it was just one of the hardest decision I had to take. But I think at the end of the day, it’s a decision everyone has to take in their career as well and do what’s right. 

What are the learnings or insights that came to you from that journey?

Wow, a lot.

There’s the way I choose the next, at least my companies that I work for. I think I learned a lot from that. The size of the organization, the funding that they have, how I look about the product and how they generate revenue, by the way.

Is it from services? Is it a reoccurring error from licenses? So there’s a lot of metrics that I know how to look on today, which I didn’t know 10 years ago. 

I know we’re coming up against the time over here. So last couple of questions for you, Alon.

Sure. 

One is like, what is really maybe a trend or something within the customer success space that’s really caught your attention that you’re really curious about and you want to go down that path? 

It’s an easy one. And I have to say, yeah.

And I know everyone is obsessed about that. And I really try to look at it, not as the hype motion, yeah, AI is going to replace everyone in the next. I’m not really a believer, especially, you know what, not in customer success and definitely not in the high touch motion of customer success.

But for me, honestly, I think I’m grateful that I’m in this position, that I can really do something new. So putting aside that I’m also rebuilding this team now at Eterra, if you’re now a leader of customer success, it’s a rare opportunity to do something that nobody has done before.

And even in, I have to say, in customer success, it’s even harder. There are certain departments within the go-to market motion that there’s already best practices and there’s an abundant of tools that are already being used. In customer success, it’s just starting.

And you don’t have these playbooks yet. And you don’t have the products yet that I envisioned. And reshaping and thinking how customer success is going to be transformed in the next few years, that’s a huge opportunity.

And I’m grateful also that my company understand that. And I’m giving the mandate to design and operate in order to achieve this transformation. Obviously, we have our goals as well.

You want to be efficient and you want to scale in an efficient way. But I truly believe this is the point where customer success is about to transform and have their next big shift. If customer success was born with the SaaS motion, this is the next job.

And I talked before a little bit about communicating better with end users. I have to say, this is where I think we were able to make a dramatic change. Because we, in high touch still, you don’t have time to reach end users.

And AI could help us understand data better, building customer success plans better, and creating plans. I see it in a way that it will be a hybrid between high touch and scale and allowing high touch CSM being able to execute their strategies and reach eventually in a personalized way to the end users as well and driving adoption. And we all know how adoption is important.

And adoption obviously leads to growth and retention and et cetera. 

Yeah, fantastic.Great point.

I mean, I love the fact how you actually double clicked on what really mean by AI and customer success. And there’s so many nuances in there. So yeah, I look forward to hearing more from your team and from you downstream in how you’re bringing and incorporating AI in customer success.

So final question for you, Helen, is if you were to turn back the clock and you could go to day one of your go-to-market journey, what advice would you give to your younger self? 

Be patient. I’m a very eager and competitive person. And when you started, at least when I started the career, you’re always thinking, okay, what’s next? How am I going to develop myself? How am I going to get to the next bigger role? And it’s really a journey.

I think every role that I did, I learned. And to be good at what you do, I don’t believe in jumping from a junior role to a very senior role. The mileage that I did, I learned so much.

The complex projects that I had, the scenarios. Dealing with all of that is what brought me to what I am today. So, but back then, you know, you’re not sure.

Will I able to make the next jumps? When will I’ll do it? So it’s being patient and just tell myself you’re on the right path. Maybe buy some stock options of VBR or Bitcoin back then, but that’s a whole different story. Yeah.

Very good. Yeah. That’s a great point to end on.

Be patient. And yeah, growth and success will eventually come in your journey. So thank you so much for your time, Alon.

I enjoyed the conversation, especially the fact that you are the first customer success leader in the podcast. I personally learned so much and I’m sure the listeners who are especially focusing on customer success would enjoy and value this conversation as well. So thank you for that.

Thank you, Vijay. It’s a great honor to be here. I’m a big fan and thank you so much.

In this episode of the B2B Go-To-Market Leaders Podcast, Vijay Damojipurapu sits down with Cy Khormaee, co-founder of AegisAI, to explore his journey from computer science research and early Microsoft days to entrepreneurship, Google, and eventually building AegisAI. Cy shares insights into curiosity-driven sales, the challenges of scaling security solutions, lessons from pivots like reCAPTCHA, and how entrepreneurs can stay ahead of technological and market shifts while remaining grounded in customer problems.

They dive into:

• How curiosity and problem-solving shaped Cy’s GTM approach from Microsoft through startups.
• Lessons from Contastic and Google that informed AegisAI’s AI-native solutions.
• Why focusing on real customer pain is the foundation of entrepreneurship.

The role of referrals, trust, and customer success in scaling GTM motions.
Practical advice for young professionals entering sales and go-to-market career.

Connect with Cy Khormaee on LinkedIn

Connect with Vijay Damojipurapu on LinkedIn

Listen To The Episode:

Curiosity-Driven GTM: 3x Founder Cy Khormaee on Building AegisAI

So first and foremost, always the question that I start off with, I mean, there’s a question I always start off with for the podcast, and the listeners love it, which is how do you view and define go-to-market?

Yeah, I mean, for me, it’s all about getting the right product to the right person. You think in a perfect world, everyone has everything they ever need, but look, it’s a messy marketplace, like new things are happening all the time, needs change. It’s actually really hard, both from the buyer’s side and the seller’s side, to make that great connection.

And I think the art of go-to-market is efficiently bridging that connection. So you almost imagine the platonic ideal of go-to-market is imagine every single person that could benefit from your product instantly had it in their hands with no transaction cost. And when I think about the effort of go-to-market and go-to-market professionals, it’s to go from a state of the world that is total chaos and no one has what they need towards that platonic ideal.

Yeah, no, that’s a great explanation. I think this is the first time I’m hearing, putting it more succinctly and magically, if you will, which is, hey, a certain set of people have a specific problem, you have something that will solve the problem, connect the two, as simple as that. I mean, it’s very simple to say it, but it’s super, super hard to execute against it.

I think that’s well said. That’s exactly right. It’s simple, but it’s incredibly hard.

And for what it’s worth, that perspective, I don’t think it’s changed my entire career to go-to-market. So it’s always trying to solve that problem and every different variant, every different problem that every different set of stakeholders, but it boils down to those two things. Yeah, fantastic.

All right, let’s take a step back, big picture. And if you can walk our listeners through your career journey and what led you to what you’re doing today, we’ll get into startup after that.

Yeah, I’ll try and get my life’s journey in two or three minutes.

And it’s a bit of an interesting journey, particularly for a go-to-market audience, because I started my life as a computer science graduate. So, actually, I was doing natural language processing research. I was thinking about doing a PhD.

These are not typically things you see, I’m sure, for the average go-to-market leader. And so those led me to take my first job at Microsoft. I built a lot of early ETL solutions.

The first version of Microsoft Ad Center was all kinds of built in my team. And then I got my first taste of go-to-market. Actually, there was a great leader named Philip Desautels, whom I ended up working for.

And I remember I flew out to Boston to meet with him. And he was telling me, Hey, I’ve got this great team. We’re helping universities adopt developer technologies.

You should come and be a go-to-market person here. I’m like, oh, sounds cool. I don’t know anything else other than that.

I remember he had a gold Rolex that on the back of which was said, Thanks from Bill Gates, signed. They’re like, Wow, that’s impactful. I don’t really understand what this is, but I like it.

So let’s go. So I picked up my life, flew out across the country, and took a role I’d never done before. And yeah, I was just off the races.

Also, I think I was one of the youngest reps in the field. So I think I started at Microsoft when I was 19 years old. I think at this point I was 20 or 21.

So, just barely able to take a customer to a bar at this point. Wow. We’re getting out there and selling.

And it turns out I loved it. I love the aspect of really helping customers. It really fit the natural curiosity.

I had to really understand what they were trying to do. And then the freedom to run your own business. I was running a mid-Atlantic territory for Microsoft.

And there was just a lot of latitude in doing what you thought was best to meet your customers’ needs and finding ways to help them. I remember one of the best relationships we built was with Georgetown. It really started with me helping a professor get a codec working before her class.

I think all the banks were super useful. What else can you do? So again, it’s all in service of finding that solution for the customer. So after that, I spent a decade as an entrepreneur.

I built a company called cmls.com in the commercial real estate space, built a company using AI and NLP to automate sales outbound, which is becoming a very hot theme now. But we were one of the earliest companies to do this back in 2013. And we were funded by Lightspeed Ventures in that case.

We sold that to Sugar CRM. So we became part of their Sugar Intelligence Suite. And all of that led me to Google.

I just made that one note on just being an entrepreneur, I feel like it’s all about go to market. For me, when I look at the problems, technically, we can usually figure out the technical problem. They’re hard.

You need brilliant engineering to get that done, but they’re usually there. The real binary thing about entrepreneurship I found is identifying the customer pain and making sure you’re very clear on that. And they’re going to try all kinds of things to solve it on building products, on creating solutions, on delivery mechanisms, on marketing, on sales.

All that’s going to change a lot, but that core customer pain is not going to change. If I think about our current business, by the way, like email security, people are getting phishing and spam for the whole 50 years email’s been around. That hasn’t changed.

So it’s a mission that’s very clear for us. So all of that really is what eventually brought me to Google, where I got to work with our current team. And at that point, I ran browsing and reCAPTCHA.

And really, my mandate there was to take these incredible pillars of the security community, things that have really protected most of the internet. When I say most, I think browsing today protects around 5 billion devices, which is the vast majority of the internet. And reCAPTCHA protects more than 7 million websites, which again is maybe the majority of the internet.

So these incredible platforms are being them to market as enterprise solutions. So, really empowering them to grow from being these incredible free platforms to pillars of Google’s GCP business. And so we got to see a chance to build go-to-market enterprise motion and security for the first time with this team, all while getting to work with some of the biggest ecosystem players, all the way from India Railways, all the way to Spotify.

So we worked forever and across the board. And really, again, just coming back to that process of helping connect this great need. In that case, it was defense against phishing, defense against credential stuffing, with the customers that needed it at scale.

And then all of that was really the accumulation that led to me founding AegisAI with Ryan. So we worked together. Ryan was my engineering partner at Google.

Bhadra was our head of product, was one of the product managers at Google. And so we all worked together at Google for five or six years. I think between the three of us, we’ve probably been around at Google for 30 years working on this problem.

They all worked on the space in this area for Google with me. And so we said, Hey, we saw this rise in AI-powered attacks coming. It’s really getting more sophisticated.

It’s really getting more complex. There must be a different solution here. And so we got inspired to go build the agent-based solution, something that was LLM native, founded this, and turned out it worked really well.

It was an incredible journey, and it was really something that worked better than we ever could have expected. A quick story on the actual founding was after Google, Ryan, and I had continued to surf. Folks can see maybe in the background, I got my surfboard.

So we were surfing in Aracera and Portugal together and reading AI papers as geeks do when they’re on vacation. And we just had this intense realization that we had to build something now. This was the moment when agentic and reasoning technology was really taking off.

The threat was more real than ever because adversaries were using that, and we needed to put the right defense in the hands of the defenders. So that trip, we flew back to New York, and we just got to work building and iterating. And then the rest, as they say, is history.

Wow, man. You packed an amazing, what, 10, 15, 20 years of your life into what, 23 minutes, A-plus job for you on that. But there’s so much to unpack. And I’m sure even if you spend the entire 60 minutes just on that, I’m sure I’m doing a lot of injustice in terms of uncovering so many things. So let’s spend maybe a few minutes. So, going back to your time at Microsoft, you moved to your first go-to-market role. And that’s when you discovered the whole thing, that first of all, you were curious, that really bubbled up. And then something else was trying to understand the problem of a customer. So expand on that. I mean, I’m thinking more from the listeners who are either young in their go-to-market journey, or they’re trying to get better at that. That’s super critical. So expand on that, if you can.

Yeah, it’s a great question and a great lens. Let me kind of think through that a little bit there. So, just to understand the problem, what we’re solving was a very nuanced problem in that team at Microsoft.

So we were part of what was called the Developer Evangelism Organization. And the very specific problem that we’re solving was that companies, in fact, Microsoft, and other companies wanted to implement more Microsoft technology. That was a fairly universal thing.

And their problem was, there weren’t enough people trained on that technology to successfully meet that demand. We actually got into the business of training. So we do things like writing curriculum for universities, getting more students trained on .NET, helping people understand the great tools they had back in the day, like SQL Server and integration services.

So again, just on the problem, whatever the problem is, you just have to understand it. And then the solutions can be very different. So in this case, we’re actually largely creating, promoting, and helping train for these developer tools for companies to implement more Microsoft technology.

It’s a very odd problem if you think about it. One, when you hear about it, it’s fascinating. Of course, that role evolved from being that into selling more of these classic developer technologies.

But the problem itself is very interesting. I think that’s one. And then two is on what young people can learn.

And actually, I just had this realization because I was talking to a young person just a couple of days ago who’s interested in entering the sales industry. And traditionally, you enter by cold calling. It’s very frustrating to get into sales.

And that’s kind of how you do it. But I think today, it’s very different. It can be led by technology.

There are all these new tools out there, you know, like Clay, all the new stuff coming from HubSpot. It’s very different and automated. And I think there’s a new era there.

And so it does harken back to even my start at Microsoft, where there were a couple of things we were doing that are very different. I did that was very different. So I think when I started again, I was 20.

I was the youngest rep on that team by a decade at least, and probably the average age by 15 years. I think one of my colleagues responded saying he had a t-shirt that was older than me, which was true. He actually wore the t-shirt at some point, which is super funny.

You know, I was using tools. At that point, I was one of the first people on the team to successfully use mail merge to do mass mail, which is mass mailings back in, you know, the 2010 era. That wasn’t a thing that you really saw, especially with corporate executives.

Imagine being the only person doing that. Incredibly powerful, automated list building through, at that point, they were called Upwork. So, contracting platforms.

And then we also did Facebook advertising. So we were acquiring Facebook users for a nickel a piece. And we didn’t even know that, but we knew I was getting an email.

I’m getting the right to contact this person for a nickel. That’s a screaming deal. And so the way I distill those learnings that are obviously not relevant today, because the world has shifted to today, is that marketing and go-to-market is an intensely competitive zero-sum game.

Like your message needs to beat out everyone else’s. And the way to do that is by leveraging new tactics, new techniques, new technologies, and new marketplaces. You must be looking towards the future and using what is new, or you’re going to be drowned out.

And so if you’re a young person or a person early career, thinking about entering the space, I highly encourage you to master, not the old tools. Don’t worry about Salesforce as much. Don’t worry about as many of the things that everyone else in the org will know.

Worry about the things that they don’t know. Like what I love when I talk to sales folks who I’m going to work with is, teach me something new. Teach me a tactic, teach me a tool, teach me a way to use Clay that I’ve never seen before.

And in fact, one of the reps we’re just going to hire soon, that’s one of the ways he really impressed me, is that he is more up-to-date on the recent tools to scale, go-to-market in a customized way using AI. And I’m like, great. I want you on my team because not only do I think you know something more than me now, but you’re kind of proven as a curious individual who’s thoughtful about both how to sell, as well as how technology works, who’s going to keep me ahead of the game in the future.

And so anyway, I think it’s a phenomenal time to enter, become a seller as a young person. I think this is a golden era where you get to go in there and experiment and innovate and create new things with AI instead of, you know, dialing for dollars, which, you know, I can recall doing plenty of that in my early career. Yeah.

No, again, I think you hit on so many important points over there, Cy, which is curiosity. If you keep that thread burning, if you keep having curiosity fire burning, you’ll find ways. You’ll find ways to, first of all, figure out how to identify the problems, how to identify the right set of problems, and innovative ways to solve them.

I think that’s a common thread across. It doesn’t matter what role, what industry, or how many years of experience. Yeah.

Also, add it really, if you extend that from the problem to the customer, and you start to really understand the customer as a whole, you use it to build the relationship. Like, the biggest compliment I can get from a customer is like, Oh, I feel like you really understand me. And you can follow these customers in different roles because they know you understand them, you understand their business, and what they’re trying to do overall.

So you can add value to them in many different ways, well beyond maybe whatever specific solution you’re selling today. And there’s going to be instances where you get to work with the same people, sell to the same people over, you know, my career is almost 25 years. So decades of time selling and selling to the same person because you’ve built that trust and that understanding.

And that extends all the way to their business and the person, not just the current problem they’re serving today. So you can actually extend that even further to these big relationships that will really help you build your career over time. Yeah.

Very cool. And then we are still only in the Microsoft part of your journey. So if you go to the first company that you founded, which is CIMLS, is that how you… It’s CIMLS.com. CIMLS.com. Yeah.

That’s a real multiple listing service. Still up and running today. The idea was it is a multiple service for people to post, buy, and sell commercial real estate.

So the folks don’t know, you know, there’s a regulated market in residential MLS, and the MLS, every company we work with works for that, right? But it’s less regulated on the commercial side. There is no similar MLS that’s run by, you know, the organization realtors. And so it was left at that point up to companies to go build those. And so we kind of built that over time and really got to see at that point, the power of data at scale, what it looked like to really go-to-market from a small company standpoint, because you’re really out there, you know, with Microsoft, it’s a bit of an unfair advantage. You never knock on a door and you’re like, hey, I’m from Microsoft.

Well, mostly people want to talk to you. Most people understand who you are. And there’s almost always an existing relationship. It’s the easiest way to sell. You got the power of the brand behind you. That’s impressive. And by like the biggest brand, one of the most, you know, this is during the Balmer era, like most well-recognized sales teams, well-oiled machine, these people have it on lock and still do to this day. So it was a great place to get trained, but it wasn’t the hardest challenge you could face. I think the hardest challenge is, hey, I’m coming from this new brand. You’ve never heard of me before.

Yeah. Brand. Yeah.

And you may not have even heard of the category before, because this is the point, there wasn’t a category for these commercial, industrial multiple listing services. And so to go out there and educate the market in commercial brokers about how this worked, we had to enable them to start to transact on this platform, really understand how to use the internet, right? This is all a very early era where most of these professionals were, you know, very high-end. They had a small set of relationships with these brokers and buyers and people doing development in the space, how the industry worked, you know, you’re selling, you know, 20 to a hundred million dollar properties. It’s a pretty handy hand deal. But as it turns out, even at that rate, creating a liquid market with the internet and with online postings is very powerful because then people can get to know each other. There’s more exposure for every deal. It’s very much a win-win for everyone to create a more efficient marketplace that didn’t exist. And, you know, that really was a mixture of that good go-to-market as well as unlocking the power of AI and data. I remember one of the first things we did we put a lot of the city of Portland listings online ,and, you know, they have this data that’s publicly available, free to use as part of the public record.

Yeah. I remember paying $300 for a DVD at the city office. Putting that into our database and then making it searchable, indexable, and making it accessible.

So if you think about that problem, you know, every broker, every buyer would have to go to the city office. Yeah. Get the DVD, load up. Yep. Yeah. Go search a CSV file, which is not what your typical broker wants to do on their Saturday morning. Put it online on easy websites. So on their phone, they can go in there while they’re on the job site and search it and see what’s up and get educated and then reach out to that buyer. And so again, it’s back to that simple thing of giving the people what they want, making people’s lives easier, and leveraging the right technology to do so. So my bigger question is, so here you are at Microsoft doing developer evangelism. Yeah. And then you switch industries, switch domain,s and go into CIMLS. I mean, what is it that actually took you there? Why?

Yeah. No, it’s a great question. So, actually, this is a company that started with my dad…

Yeah. No, it’s a great question. So, actually, this is a company that started with my dad.

And so my family had been in the commercial real estate space for a while and saw this problem firsthand, where we’re relative newcomers to the real estate market in Portland. And we recognize how deep the real estate relationships go. I mean, one of the good examples, one of the families that has a lot of real estate in Portland is the NATO family, and they have a highway named after them in Portland. And so you’re like, okay, that’s kind of how deep these run. If you want to be a newcomer or you’re like an immigrant family, as we were coming in and starting to kind of play in the real estate game, you actually want a more liquid marketplace. 

And so we saw the problem firsthand. I understood a lot about data and technology and how to kind of put all this stuff together. And so we said, hey, there’s a really big opportunity here. It’s the right place. And then maybe lastly, I had a really strong drive to own my own business. I think Microsoft was great, and it gave me a wonderful taste of what it was like to run your own business. And I was like, I like the freedom. I like eating what I kill. I like kind of surviving on my own metal and merit. I really love the harshest form of meritocracy. So going from an engineering role is pretty cushy. And you go to commission sales, you’re a little more in that ballpark. And then you go to be an entrepreneur, and you’re all the way there. You kind of joke, you’re like, your death is your default. If you do not succeed, your company will fail. That is the current state. So you must succeed. You must earn that right to exist in the marketplace. By default, you don’t have it.

Yeah. Cool. And then it looks like you had an exit, and then you went to Lightspeed Ventures.

So EI slash fellow, is that right?

Yep. That’s right. And so the quick history there was I had a great exit, got to work with folks at Sugar. We were able to commercialize that. So I think a lot of the stuff you still have in the Sugar Intelligence Suite is still stuff we built and sold them at Contastic. So very happy. There’s value there that carries forward to this date. Somewhere along the way, I went to business school, so did my MBA at Harvard. And I still had an intense desire to build.

And so, prototyping things all the time. And in this case, I had been inspired by my time as a seller. So I’d seen the power of technology firsthand in sales. And I said, hey, there should be, in this case, a mobile CRM. It’s crazy to me that you’re writing notes on your phone or not writing notes at all. And then going back and inputting them into your CRM. And so this is a bad solution. There should be an easier way to do note-taking on the fly, to look up customer data on the fly. So I’m going to meet Vijay. Let me look at his LinkedIn profile. Let me look at what’s happening in the past. And this was in 2013, 2012, I was working on this.

I took this to Chris Sheppey at Lightspeed as part of the… He was one of the leads of the Fellows Program. And I was like, hey, let’s develop this. Let’s kind of build here. And so he was kind enough to take me in and work on developing that solution in-house that eventually became Contastic. We’ll talk a little bit about pivots and a couple of things we learned there. One is that people really don’t want to take notes on a mobile phone. It’s a thing that every sales manager wishes their team did, and they wish they took more notes. But the sales rep actually wants to do it.

And so quickly we pivoted from that into really living in the inbox and really fitting with a seller’s workflow. Because if you think about most sellers, most professionals, what’s the first thing they do in the morning is they go in there and they check their email. Great. Let’s actually put it there.

And so the way our technology worked was behind the scenes every night, we’d look at all of your Salesforce interactions, everything on LinkedIn, the news about your customers, what we thought your pipeline looked like. We use AI, by the way, to do all of this. This is, again, an early version of AI using NLTK and the Stanford Parser, and very early iterations would then become LLMs.

And in the morning, you’d come in and you’d see a bunch of little blue emails that kind of looked like emails. We input them via a Chrome extension. It’s like, oh, you haven’t talked to Vijay in a couple of days. Here’s an article about his business. Why don’t you reach out? You clicked on that, and it would pre-populate an email. It said, Hey Vijay, it’s been a while, man. How’s it going? I just saw this article. I was thinking of you. Let’s grab a coffee or something.

So we basically have the system pre-populate all that email. So as a seller, you just went in the morning. You didn’t have to do the pipeline review or think about what to do; all that mental mechanics to figure out what happened with all the account details. You just click that box. You do a quick spot check on the email and make sure we didn’t miss something that happened in text or off-platform, or something that maybe is more relevant. And then you could go.

And the beauty of that is that by shrinking the amount of time and energy it took to send these emails and do this follow-up, we could essentially enable every rep to carry a pipeline bucket that was 10 times bigger than they could before. And as we all know, one of the great secrets to sales is that if I’m in touch with more people, but maybe we’ll have more activity, more deals are probably going to shake out of that sooner rather than later. And it’s fairly linear.

And that’s a really powerful lesson. By the way, I learned at Google too, where by doing this mechanically, I was able to carry a pipeline that was 10 times bigger than anyone else. I was really able to be a top-performing rep because of that mechanized approach. And so building software for that was something I was really inspired to do with Contastic and at Lightspeed.

Yeah, no, fantastic. And thanks again, jogging me back to the memory of Contastic because that’s where you and I met, and our paths crossed at SugarCRM. So I was the product marketing counterpart for SugarCRM Hint. That was the branded name we gave for Contastic back then. And it’s still surviving. So I think we should both take credit for what we built is forever, we’re going to live on forever.

Yeah, I mean, I’ll take a very small credit, but kudos to you and your team. I mean, definitely, you guys did something.

So my brain, as you’re sharing all your stories, Cy, it switches to something else. So for me, I met go-to-market leaders, founders who are really strong in one area, I mean, on the business side mostly. But what I’m sensing is you have that, of course, curiosity, you have the knack of understanding the buyer and the problems, but there is also a part of you that’s very tech-oriented and geeky. Yeah. So expand on that. I mean, how did you figure that out? How did you build it? What do you do? How do you balance the two?

Yeah. It’s an interesting question. I mean, I kind of joke, it goes back to my family. So my mom was one of the very early sales reps for Merck. So she can tell crazy stories about her CRM. She was mailing in forms, and she was driving through the ash cloud of Mount St. Helens when it erupted. So she’s a very well-tuned seller.

And then my dad is an engineer. He was one of the very early engineers who developed the inkjet technology for Hewlett-Packard and is still an electrical engineering professor today. So I think it really started at the beginning, where I was just incredibly lucky to get, of course, the genetics, but also the training from these two very different people who really helped develop both sides of my brain.

And then in university, I just always had a deep fascination for technology. That’s why I studied computer science initially. And then that sales side really came out as I was running that business for Microsoft. And I found what was really powerful is exactly what you pointed out, Vijay, that combination of a technology-aware seller is really powerful.

So I was kind of a kid with my co-founder, who’s deeply technical, spent a decade working on detection technology at Google. He had a CS major before that. I understand just enough of what the really smart people are saying to explain it to the rest of the world. And that’s always where I sat as a product manager, as a seller.

That’s a continual theme for me in the roles where I know enough to have a really good conversation with incredibly smart people about what they’re doing, and then help them package and communicate it to everybody else. I think that’s been my very special ICP or special intersection of talents in the world.

Yeah, very cool. And something that really caught my attention, going back to the time when you were talking about you and your current co-founder surfing in, is it Portugal or Spain?

I think Portugal.

Oh, it’s Portugal. Yeah. You mentioned something that really caught my eye, and where there’s also selfish interests or wants for me in going down this path is that I want to teach my kids that specific aspect. You mentioned you actually sat down and read research papers. That gave you that moment, or an aha that there’s a business problem out there. So expand on that. What is the thought process like, and how did it go about doing that?

Yeah, it’s a great question. My daughter’s a little bit young; she’s three, so we’re not there yet. It’s a question I’m sure the rest of the audience is wondering too: how do we build natural curiosity into people? And I’m going to harken back to my parents. So both of my parents, my mom later in her career became a teacher, and my dad, of course, is a professor.

So I had the great gift of not only their diverse skillsets, but also their deep steeped of pedagogy. They thought a lot about this, and they thought they were very deliberate about how they kind of helped us explore our world. And they really did well, the biggest thing they did was they took a very light hand. They really let us follow our interests and they’d encourage and support them. And if there was a challenge with their support, they kind of know just to go figure it out.

But they really framed the world as like, look, it’s a big world out there. There are a lot of things you can think about. There are a lot of problems. What’s interesting to you? And when you’re diving in, we’ll support you, but you’ve got to go figure out the answer. You’re very capable. Go figure it out.

And so that’s always, I think, been the start of my curiosity. And then, as I think about why we’re reading these research papers, it was because of that curiosity. That curiosity leads you in different directions, where we see trends. And it was pretty obvious at that time that AI was a trend. I mean, look, it wasn’t pretty easy.

We’d seen the early versions of TensorFlow and the transformers of Google, because we were there in 2017 when it was invented. So we started to see that we’re like, hey, this is really significant. And then in 2022, 2023, we saw the GPT land and saw the impact of that. And then it’s kind of patently obvious.

And then you’re like, okay, this is going to be a trend that’s bigger than the internet. This is going to be a trend that’s going to transform life larger and faster than anything we’ve ever seen in our lives. Yeah. Let’s understand everything about this, and let’s understand what the frontier is, and let’s understand how this applies at a technical and at a business level.

Because I believe strongly, and I know we know this, but I teach the AI course to MBAs at UCL as well. How do we think about crafting businesses in a different way? And so that’s really what informed us to read these papers is to look out ahead of the curve and think about what was coming.

What’s interesting about computer science papers and research papers is that they often significantly outdo the coverage of what technology can do. If you think about that as an example from neural networks, I kid about this with a good friend of mine, who I went to computer science school with, who’s in the AI space now as well. It’s been theorized since well before 2000 that unsupervised learning and neural networks could get us here. There have been papers written, proofs, and all of these things were done in the literature in 2000.

That’s true, yeah. Only came to fruition today. So I want to really look into the future. I want to do something by looking at research and looking at what the smartest people are thinking about as the theoretical foundations that might exist in the future.

The difference is, I think, the pace of technology is moving without hyperbole, like 10 to 100 times faster. So what took about 20 years for the last generation will take two years. When I look over the horizon, for me, the horizon is six to 18 months, technology, which has never been the case before. So that’s what really got us inspired.

And then maybe to close it that way, thinking about what I can do for my daughter to really encourage this, is just to encourage her to solve more of her own problems. And so whenever she has a problem, I think her first instinct is like, cry for help from dad. That’s the first instinct: get me to do it. And I got to resist, like I love her, I want to help her, I want her to have a happy life.

But I think the best way I can do that is actually by not helping her with all the small things. So she can develop the capability, the curiosity, and self-reliance to solve the big things later when I’m not there. And so when I think about my role as a father or my role as just anyone trying to educate or train, it’s giving people enough rope, enough safety, enough capability to solve their own problems as fast as possible and grow as fast as possible. So that when it’s not in my control to protect them or help them, they can solve it on their own.

Now, this is great. I mean, I love the way you actually tied in. It goes back to how your parents brought you up; that’s key. The whole go explore, be curious, and it’s up to you, we’ll support you, it’s up to you, go figure out your path. That’s a curiosity and with a support level behind it. And there is also the element of what you’re seeing firsthand at large companies like Google from a technology point of view and a technology trends point of view. So that translated to you and your co-founders saying, hey, there’s something happening in the AI world, and both of you are grounded in research papers, are the harbingers of what’s to come. So go back to that world. And so, how do you go about figuring out which research papers and on what topics? That’s key.

I mean, it’s a great question. I mean, there are a couple of ways that it’s not elegant. Like, look, you start by just Googling around and getting a grounding on the space. And what you’re really trying to do there is build a reference floor.

So when you think about, you know, PhD students, they actually write papers, they do a basic research review of like, what is the state of the art in the space? What’s ground level? And so reading like, read the transformer paper, read all kinds of basics in the space. And then inevitably, as a curious, smart person, you have a bunch of questions that occur.

You can look around at those. And then once you do that review, a couple of things will pop out of it. You’ll get a basis in terms of what the different areas are, what’s soft, what’s hard, what’s promising, and what’s not. And then two is who are the interesting people in the space? And then you dig in, you look at more and more of what they’re doing, what they’re looking into, and you can start to follow folks and kind of dig in there.

What’s really interesting with AI, though, is I think it’s one of the spaces that’s really broken the most research paradigms, where it’s really like a new category that got invented. And so innovation is coming from everywhere.

An example I could give is, we deploy customized versions of open-source models at AegisAI. That’s kind of a lot of what our core technology is. And you’d suspect, like, oh, it’s all going to be from the two or three big companies. But it’s really not, right?

We started, of course, by using the model from Facebook, LLaMA. And then we moved to the Microsoft Phi model. And then we looked at some other models from other companies in like e-commerce space and things you’d never suspect. And then now we look back, we’re using a lot of stuff from Google’s Gemma. Really, every two, three weeks, it’s a new adventure. Every two, three weeks, it’s a new set of technologies.

And it’s really not bound by just the big companies and big institutions. I think it’s such a giant gift that, like, hey, this idea of an LLM and a neural network works, and it got dumped on the world. There are so many different ways that we can dissect and understand this technology. It’s almost like a giant alien mothership with all this new technology landed in New York City. And everyone there can go on the ship and look and poke and prod and figure out what to do with it. Just all kinds of innovations coming out all at once, which is incredibly exciting.

It does make this research a challenge, but I just think kind if you continually follow the thread and you’ll get to some interesting conclusions. Maybe the last thing I’ll add there is just take those and then immediately implement them. So, I think there are a lot of things in theory that are like sound good or are fully understood in your head.

I’ll tell you what, when you deploy something in production and you look at the quantified results, then you really know what the nature of the thing is. And so, taking that from that initial curiosity, where you’re looking across all the papers to reading and understanding the content of the papers and what’s going on and what technical implications this has, and then taking those implications and then deploying them live into production, that journey is really where you get to truly understand every aspect of the technology in a way I find deeply gratifying.

And of course, at the end of the day, you get to solve that customer problem, which is the whole point in the first place.

Yeah. Wow. I mean, clearly, again, I go back to the whole thesis behind how top-tier VCs invest in startup ideas. And just listening to that last few minutes of how you are talking about how you uncover the problems, the rapid pace of the technology changes, and connecting it to the customer problem. I think that’s the magic connecting the dots. It’s not easy. It’s only a very rare few people on earth who have that combination.

Yeah. Well, I don’t know if it’s that rare, but I think that is the combination to look for where you’ve got the right problem. I think one of the mistakes people make, by the way, is they go the opposite way. They find a really cool technology, and then they try and point it at a market that either doesn’t exist or is too small.

You can never know because the problem isn’t real. Going back to our first conversation, where you really need to start is a big and real market. And for us, email security is a big and real market. Look, it’s $5 billion spent now, it’s going to 10 billion. Every person who uses email can tell you a story about how they saw phishing, spam, or malware. It’s universal. It’s a clear problem.

Now, it’s very hard to solve. We have to work hard to solve it, but there’s no doubt that the problem exists. And then to your point, the second part of the VCs’ love is seeing a technical breakthrough that has evidence. And what we showed them was, hey, we are deploying this model on top of existing, in this case, email workspaces of customers of large companies. And we’re finding a lot of bad stuff they’re missing. It’s proof that the technical innovation solves the problem.

When you put two things together, you’re right, you get real magic. But I’ll emphasize for any founders or entrepreneurs or aspiring entrepreneurs out there, focus on a problem, focus on a big real need first, because that’s the immutable thing that will not change. If you don’t have that, you’re not going to magically find one.

Start there and then innovate, and then find different ways to solve that problem. There are a thousand different ways to skin a cat. And so you can really figure out what that is, but the fundamental problem won’t change. So you’ve got to start there.

Yeah. So coming back to the focus, the central theme of this podcast, yes, it’s about customer, problem, product, and tying all of those things together. Let’s go back. I mean, if you can jog back in your memory and pick and share a go-to-market success story and a go-to-market pivot story. I’ll let you choose which one you want to start with first.

Yeah, I know. I mean, let me think about that a little. There are a lot of good ones.

I know, a lot of… I can clearly see that. Yeah, totally. Think in your head. There’s a lot. Oh, there’s a lot.

Let me start with the pivot story, because I think it’s a really… I think that’s the more interesting one, because success is fine, but we all like to choose… You learn the most from the pivots.

I think where reCAPTCHA started is maybe one of the most interesting ones. So I’m sure we all know reCAPTCHA is the little thing you have to click on before you get into the website you really wanted to. Is it a stop sign? Is it not? Is it a crosswalk? Is it not? The existential question we all wonder about.

And where reCAPTCHA really started at Google, when I got there was a way to do machine learning training. That really was kind of the purpose. It was leveraging a little bit of anti-spam to get there. But we’d reached a very interesting crossroads for that specific technology, that image technology we were clicking on.

One was that it wasn’t working very well anymore, because there were real adversaries that had real humans working to solve them manually, who are going to be better than you or me at solving them, because it’s literally their profession. The second was that the machine learning data coming back from it was less and less valuable, because Google started to build its own custom labeling systems on its own.

So both sides of the business were being squeezed, and they had to kind of figure out what else we could do. And at this point, they were reporting through the maps or the geo-organization at Google, and I was part of the security organization. I’m like, hey, maybe we can amp up this thing that has a massive footprint. It’s got a lot of the right makings to kind of stop spam on the internet. But we just need to find a new way to apply it.

And in talking to that team, they’d started to build a new system they call V3, that instead of solving the images, they solve it by looking at the behavioral patterns on the site and using that to stop the attack. Now, the benefit of that is it’s an incredible user experience, because there is no user interaction, and it keeps you safe.

In fact, on this call today, the Zoom call is protected by reCAPTCHA, and we never solved anything because it’s observing all the interactions and being sure Zoom bombing isn’t happening. That’s just an example today of how it works.

And so again, I take no credit for the innovation. Very smart people had built that before me and were kind of figuring out how to bring it to market. I said, Hey, well, the way for us to bring it to market is to pivot this tool from machine learning and just spam into this new space that was happening called credential stuffing.

So many passwords have been leaked on the internet over time. It was very easy for adversaries to guess the right password and hack into your bank account or email, whatever else they wanted to get into. And so what companies needed was a layer of protection that detected not just who was logging in, like who was holding the key, but also where they were coming from, like what’s the nature?

So I kind of joke, it’s just like you hear someone kind of jiggling the keys at your door. That’s not enough. I want to actually look through the peephole and see who it is. I need both of those.

Allowed companies to do that. And so we pivoted this kind of anti-spam ML training technology into this anti-fraud world, this credential stuffing world, and really built a $100 billion-plus business out of this in a very short order. And we did so all with pivoting this business, again, like pointing this technology at an existing problem or a new problem that was really urgent.

And so that was kind of one of the pivot stories. Let me take a pause there and see if that story made sense. There’s a lot of technical jargon in there. I have to unpack whatever’s helpful.

Yeah. So a couple of things over there. I’m thinking from the wider audience spectrum point of view. I mean, I get the technical aspect and the problem it solves, but what’s not clear from a listener’s point of view is the business aspect. How is Google monetizing this technology? Got it.

So it’s very simple. So every time now that you see an interaction that you want to get a score on from a CAPTCHA, every time, for example, there’s a login event, the customer will, in this case, Zoom, will pay us a tenth of a cent or something in that range to score it and tell them what we think. You do that millions and millions of times, billions and billions of times across the internet. And so you have that model.

What’s interesting about the go-to-market for this, by the way, is that a lot of it was driven through product-led growth. So a lot of this was adopted just by engineers inside large companies. One of the great stories was Pinterest. A great team, an innovative team there was looking at adopting the solution.

They adopted it, and they were using it at scale in Pinterest, which is a giant business. And then their team calls like, hey, so we got to get our execs together and we got to do a real deal because we can’t be paying lists on this. We’re going to production. I’m like, great. That happens to be the best sales call you could ever have.

And so that was kind of a unique thing that was part of this business. And so it was very powerful. And then of course, we got to partner with some spectacular go-to-sellers from a former ex-company, Chronicle, that became our sales team led by Aaron Pan and John Turner. And we were able to really scale out with them.

So we had this very powerful motion of our product team, our engineering team, and the sales team, all very closely aligned, all working together on all aspects of the product, everything from go-to-market to kind of this sales motion. Because the sales could actually come from the website, even for very large customers. They could come from our sales team. They could come from relations we had on the product team.

We really all worked together. And I think one of the great learnings from that was how such a close partnership between those three functions — and honestly, sometimes can have less than steady relationships — that incredibly tight partnership and bond that by the way exists to this day can really supercharge your business.

Fantastic. And your role was playing the lead product manager for that. Is that right?

Product director across all these businesses.

Fantastic. So question here. I mean, clearly, yes. When everything works fine, it’s amazing. But there are so many days in between where things are falling apart. Yeah. What almost broke you down in this journey?

Yeah. I mean, there are so many. I mean, I’ll tell you the start, right, where we were working with this business. And initially, like, no one believed there could be an enterprise business built out of this.

So I remember standing in a room saying to our GM and like Everett and all the other execs, like, hey, I’ve got a thousand customers I can sell to. Like, this needs to be a real business. We need sellers. We need support. And there was a year or so we couldn’t get a lot of interest.

And so, you know, the way I solve it, by the way, I think about my inclination seller as well. How do you solve a sales problem? Yeah. I rolled my sleeves, put on those shoes, and went to sell some stuff.

But you were the first salesperson for this.

I was the first salesperson. So we sold, I probably personally sold a million, $2 million of it. I think PayPal was our very first customer, by the way. So it was a crazy deal. We did a seven-year deal with PayPal for this. Yeah.

And yeah, I was driving with, of course, in partnership with a rep in the account, and we’re getting it done. And that was a way for us to build the initiative and interest in getting a full sales team. Because then I went, took this over to Aaron, who was going to be our future head of product or head — sorry — head of sales.

I was like, hey, I’ve already sold a couple of million dollars of this stuff. You’re really smart. Like we could do this. We can scale this. He immediately got it. It was like, hey, let’s roll this technology, enter the opportunity.

But I’ll tell you, you know, if you’re a PM or you’re in an organization or trying to get them to start a new product line of sales, the best gift, the best proof is to go to a sales team and say, hey, so I sold like a million dollars on my own and I’m not very good at sales. Like, you guys are good at sales. What do you think you could do with this? And then immediately, you’ll see the color signs go off in their eyes.

Exactly. So how did you go about doing that million or $2 million in sales? Like, break that down for us, if you can.

Yeah. I mean, it’s nothing different than any other seller, right? You go out there and say, Look, here’s the problem. I believe the problem is credential stuffing. I believe people with really important accounts are going to be the most worried about it.

Let me go out and see which GCP accounts that I can reach have this problem, and let me sell to them. So I cold-called my way in either through the reps or directly to the account across all the accounts. I started giving the initial presentations, kind of gauging interest, ducking and weaving with the initial product flow, and trying to fit the problem statement they had.

And it was it. So again, there’s very little magic in that process. It was simply like going back to the roots of hard notes, getting out there and making sure you reach the customer, you understand their problem, and then you understand if there’s a fit between the problem and your problem.

Fantastic. So let’s come, I know we are coming up against time over here, 10 more minutes, but let’s cover the major chunk about AegisAI now. So your journey at Google brought you in touch with your current co-founding team. And so explain to us, I mean, you did touch upon that, but explain to us, like what is the foundation problem that you’re solving, and how are you thinking about it from a go-to-market perspective?

Yeah, of course. So again, the problem goes back to keeping your email clean. Like, I think everyone listening probably does not — if they look at their inbox right now, they probably almost certainly have spam. They may have some phishing. That is not good. I do not want to see that. They don’t want to see that, right? So that is a problem that’s 50 years old, as old as email.

So that is what we want to fix. And more specifically for CISOs, who is who we really sell to, we want to give them the guarantee that there is not going to be malicious content in their users’ inboxes attacking their infrastructures. By the way, the number one way all the attacks start is through an email attack.

And then second is we’re not going to block their legitimate email. So they’re not going to call us from the CEO asking where my email is. So those are the two key customer promises.

And then how do we go to market is an interesting question. The CISO space and security as a whole is a very interesting markets because it’s constantly in motion, right? So there are always new attacks coming out. There are always new surface areas, like AI in this case, where the CISO needs to constantly think about and manage the surface area and the attacks on it.

And so there’s this continual game of new solutions coming out all the time. And so CISOs are bombarded by new vendors, but they also need to interact with the new vendors to solve the new threats. And so it’s a very dynamic marketplace, but one that is very noisy.

So one of the best ways we’re able to break through this, back to that original thing we talked about around curiosity and building those relationships. We’ve done that over decades with these customers. So we’ve got a lot of trust for very technical, smart CISOs who are at the top of their game. We’re like, yes, this team is a legitimate team. What they say is real, and they wouldn’t tell me this otherwise, and they’ll protect my data to keep me safe. And so I want to take a bet on them.

So that’s really how we start the nexus. It’s kind of built that trust, that first set of customers, that reputation, and the initial set of installs to test us out. From that, we built evidence, found that we’re detecting in many cases, 20% more malware than other tools. And we’re doing so at 90% less error rate than other tools we see. So then you get evidence, and you get customers who can speak to that evidence.

And then start rolling it out through all the typical channels. We started this call chatting about our launch events we had. We had great customers come in from Salesforce to, and we had the FBI local office show up. It was amazing to get to know those folks. We’ll do threat reports. So again, to add value, we want to add value in any way we can to our customers. So keeping them abreast of what’s happening is very important.

And then the last but not least is just referrals. The best way I earn future business in a space that’s very trust-based is to win hard for my existing customers. I want them to be deliriously happy with the value they’re getting, with the solution we’re offering, with the support they get. And then tell the people in the space, because guess what? No other CISO is going to care what I have to say as a sales guy. They’re going to listen to their peers.

And so my job as a sales guy is to make what those peers say as positive as possible, which means 90% of my energy I put into serving those customers, making sure they have an amazing experience, making sure I do everything possible to make them successful, not just in my product pilot, but across their entire business. That’s what I view my job as. And they’re going to do the job of helping promote us and share within their community, because they want to share something that works well with their peers.

Yeah, fantastic. 

Especially on the last point, right? The reason why I want to have really been done on that is I’m actually helping some of the large companies and businesses around expansion and referral. Referral and expansion is the lowest CAC possible to increase your NRR, period. But for you as a startup and a founder in early stage, it’s quote, unquote, easy, because your skin is heavily in the game, you’ll invest in and you will want your best customers to actually bet on you and refer you. But as you scale, let’s say, AegisAI three or even five years down, you’ll have salespeople, you’ll have sellers, you’ll have customer success teams. They may not have that same fire or commitment as you, founders have. So how are you going to solve that problem?

It’s a great question. And look, you’re kind of getting to like, things just dilute over time. I think one important thing is like, I intentionally like to have a relatively small team. So we hire relatively low numbers of relatively very high-talent people. So we tend to hire the top 1%, like quite literally out of Google’s talent bar. Like that’s kind of what we’re hiring.

And so that helps to kind of fight the dilution. The second thing is you want to maintain continual visibility. So something I learned a lot by working with Microsoft, you think about Bill Gates would look at people’s code.

Yes.

I did sales calls with Steve Ballmer when I was there, and I was a very junior rep. I think there were 13 layers between me and Steve. And Steve was still there on the ground, selling stuff, working with customers every day.

So I think you can never, ever lose that touch, both to see what sales is doing and see what people are doing with their customers, as well as to hear from your customers directly and participate directly with them. And that kind of brings me to the last point is you never lose that.

Maybe who you focus on changes. And I love thinking about Mark Benioff in this. Mark is an incredible customer-facing leader who spends a ridiculous amount of his time in front of customers. That should never change for a CEO.

My job will always be chief customer officer. My job will always be to serve the customer, help them out. If anything is going wrong, I give people my cell phone number. I want them to call me. I want to help them.

And I never want to lose touch with that. I always view that as my number one job to see that and then communicate it within my organization. And so I think that’s how you really are able to maintain that over the long run.

But you’re right. It gets harder over time, but I would say the importance of it never changes. If anything, it increases. So it’s something over time. I’m glad you’re working on it; you’re building more systematic tools to help with this because it is a major gap in the marketplace. I see a lot of companies struggle with this mightily.

Yeah. And I think it’s one of the most underserved opportunities in the space. Totally spot on. I’ll reach out to you after this podcast, but you’re so spot on. Where I see a huge problem when it comes to go-to-market is a lot of dollars being invested in new logo acquisition, but a lot of money is being wasted and not tapped into in your existing customer base. Yeah.

I’ll add on one other thing that I’ve seen. It’s been a struggle, even as a customer of many new vendors, is I have problems that they’re not solving for me, that they should be solving. And I see them investing in go-to-market, and look, they’re two different departments, which is where this really, the problem really starts.

I’m sure technology helps. The support and the sellers don’t talk to each other. And so there are different buckets and different seemingly independent functions, but they’re really not.

If you have an unhappy customer, that’s going to torpedo 10 of your deals. You’ve got to make sure you find that customer and you fix that problem. At the same time, if you’ve got a deliriously happy customer, they’re going to bring their six buddies to your next dinner. They’re going to be like, hey, you got to talk to these guys at AegisAI. They solved my problem. I don’t have to worry anymore. Life is great.

There’s no better promotion. There’s no better detraction than that. And I don’t think you can survive if you let that go. And so companies really need to stay on top.

But maybe the last thing they need to think about is that it’s not an immediate cycle. If you make a customer unhappy, that doesn’t really hurt you until a year or two down the road. Then it really hurts you. So you really want to look ahead and really proactively keep an eye out for that before you see it in the revenue numbers.

Because by the time you see it, by the time that first rep says, Hey, we had a negative reference call from one of our prospects, you are a year or two behind the ball. What I’d love to see is more sensitivity, more tooling to keep an eye on what is happening, so you can get in front of that as the customer is facing that. And so, by the way, they also feel like you’re on top of it. You’re helping that customer in real time versus two years later, you’re kind of finally following up and you’re already kind of behind the eight ball there.

Fantastic. Yeah, I wish we could spend more time, but maybe take two next year or something, Cy. But before I leave you, one final question on a very light note, which is if you were to turn back the clock and go back to day one of your go-to-market journey, what advice would you give to your younger self?

Oh, that’s an amazing question. By the way, the favorite question I get to hear on your podcast, too, because I should make a little compendium of all the answers. I think it’s probably a little bit, but just like what we talked about, I think the number one thing isto  do things differently.

Coming to this market as a new seller, do not copy what other people are doing. If they’re doing it, do not do it. Go do something different. Because I think there’s absolute room for innovation, and that’s how you’re going to win.

Look, go-to-market is an inherently competitive marketplace. You need to find a way to differentiate. That’s how you’re going to bring efficiency. That’s how you’re going to win. That’s how your message is going to break through the noise.

And so, just number one, always think about doing things differently.

In this episode of the B2B Go-To-Market Leaders Podcast, Vijay sits down with Maximilian Gartner, Head of Go-To-Market at Brightwave, to explore how GTM leaders can balance sustainable growth with predictable revenue, while staying rooted in authentic, founder-led perspectives.

Max shares his journey from inside sales “boiler rooms” to leading GTM teams at high-growth companies, and how lessons from cold-calling, enterprise deal cycles, and sales leadership shaped his philosophy on customer-first GTM.

They dive deep into:

• Why founder-led POVs are powerful in early stage, and how they must evolve as companies scale.
  
• The critical difference between predictable and sustainable revenue, and why ignoring sustainability leads to churn.
  
• Lessons from inside sales: why clarity and credibility in the first 10 seconds of a call are everything.
  
• A Brightwave GTM pivot that front-loaded product experience, shortened feedback loops, and tripled adoption.
  
• Why “knowing your customer” (KYC) at every level: user, manager, executive, is the ultimate GTM advantage.
  
• How doubt and imposter syndrome can be reframed as signals of growth.

If you’re leading sales, marketing, CS, or product, or simply curious about how GTM leaders scale customer-first strategies, this episode is packed with tactical insights and leadership lessons.

Connect with Max Gartner on LinkedIn

Connect with Vijay Damojipurapu on LinkedIn

Listen To The Episode:

From Cold Calls to Customer-First GTM: Max Gartner’s Playbook to Scaling Revenue

The first and opening question, the prompt for you: how do you view and define go-to-market?

Million-dollar question, 

Yep. 

So I define go-to-market as operationalizing a founder-led point of view and product experience into:

Wildly successful customers.

Sustainable and predictable revenue.

Cool, I like all of those things you said,founder-led, you said, point of view, yeah, and then sustainable and predictable revenue. We can go in multiple directions just on those few keywords. So let’s start with the first point you mentioned: founder-led and point of view. Would you have changed that if your experience was more in more mature, larger companies?

Potentially. I think, take a step back. What I don’t want to communicate is that a point of view is set in time at the beginning of time, and it’s crystallized and frozen, and everybody then needs to fall behind and execute that moving forward. I view a point of view as, yes, it is sort of an original, unique insight at a certain point in time, but over time, it evolves as it makes contact with the market and with reality. It’s constantly being sharpened, as I like to say.

So I do think the context that I bring to bear is more of a kind of early-stage startup point of view. So yeah, I think that shifts a bit when you’re working at a larger organization. But I think why I use the word “founder” is because the founder is the one who’s closest to that original, unique insight that kind of bottled energy, if you will.

And so it doesn’t have to necessarily be the founder, but in my experience, what I always say: no one is a more effective evangelist than the founder, right? Nope. No one can just articulate but embody that point of view, that insight. And so that could be the founder. It could be other folks in the organization as well, but that’s just been my experience.

No, spot on. In fact, it aligns a lot with my belief, and it’s been almost validated several times over the last few years for me, which is because I’ve been having these conversations with early-stage founders like YC founders and so on.

Clearly, once a startup is conceived, it’s there in the founder’s mind. He or she and that team have a point of view and a belief in why they wanted to go down this path, right? The point of view around a market situation, why the existing solutions are not good enough.

It all starts with that, and then how their product or service ties to elevating the game for their buyers and users. Now, somewhere downstream, as the startup grows 500k, 1 million revenue, 10, 50, 100, but beyond 100 million ARR, and as we scale, as a company scales, somehow that whole focus on having a point of view gets diluted.

That’s what we have seen. It’s possible, likely, that now founders, for obvious reasons, are getting more hands-off from the go-to-market motion. But I know that the other founders still love to be in touch with their customers and market, but they’re hands-off from the go-to-market motion. And the go-to-market teams are the ones who are taking the message, all the tactics, the strategy to the market. Somehow, that focus on point of view emphasis is diluted, if you will.

I’ve seen that. I’ve seen that happen at smaller companies, and I’m sure you have as well. Where, look, you can’t replicate that. But I’m not the founder of Brightwave, right? I can translate and operationalize that point of view and embody it to the best of my ability, but there really is only one original source.

And so to the degree that you can infuse that in everything from message to culture to customer interaction, to really everything, you know, how you build your entire go-to-market system, I think you become much more effective, much more customer forward, and a much more dynamic organization.

As you know, people can smell BS from a million miles away when there isn’t that kind of authentic point of view that’s being brought to the table. They can smell when it’s just this kind of generic, something I could have taken out of ChatGPT or Claude.

Yeah, for sure. All right, we have spent enough time on the point of view. But there’s another thing that actually caught my attention, which is the predictable and scalable revenue. 

Yes.

So why don’t you spend some more time on that? I mean, that’s super critical, especially in the early stage and even as you scale, for sure. So, I would love to get your thoughts on that.

Predictable, of course. Look, everybody wants predictable revenue. We need predictability, we have to report to boards, we have to grow the business, and we have to understand forecasting. That’s sort of everybody knows, everybody accepts that. That’s not controversial.

But I think sometimes what’s lost is the first part of that: sustainable. If your entire focus is just “as much revenue as soon as possible,” what might happen over time is you find leaky buckets, right?

So let’s say you sell a bunch of features that aren’t fully baked to customers, right, and they begin to churn. Or you create friction with your buyers as existing customers, and then that prevents you from growing faster than you could within those customer bases.

Or you throw a bunch of salespeople at the problem, and maybe you get a revenue bump, but then you get massive attrition, right? And it’s like, I’ve seen over the course of my career, and I’m very focused on sustainability being absolutely essential to that predictable revenue model as well.

Yeah, that actually aligns with something that I’m pushing and emphasizing with many of my clients as well, which is to let me take a step back. A lot of times when you talk about go-to-market motion, the majority of the teams focus on new logo and acquisition, versus: how about your existing customer base and expansion, and referral advocacy?

So you mentioned churn over there, which was music to my ears. So that’s the message that I’m pushing over to my market and my customers, which is yes, it’s great that you have your go-to-market teams focus on the new logo acquisition, but do not lose sight of your existing customer base.

100%. And look, new logos will always be the lifeblood of a business. But beyond that, how much time is your go-to-market team spending using all these new tools that we have access to, to understand how our customers are actually using the tool? Like looking at logs of actions they’re taking, frustration points that they’re hitting.

To the degree that you can really understand that, it changes everything. And by the way, you know, if you look at the most successful businesses that are hyper-scalers, largely that’s off the back of, in the B2B space, massive land-and-expand motions.

Yeah!

It’s getting in the door quickly. But then, because of the virality with the product, because you understand the customer so well, and you’ve iterated, and you continue to iterate so fast, you’re able to retain and expand customers at a massive scale.

So I’m a huge fan of, for example, paid power users, however you want to define power users, as a critical leading indicator of the health of our go-to-market motion system in general.

Excellent. That’s a great point that you called out over there. So let’s switch gears. Let’s take a step back, bigger picture, wider time horizon. Why don’t you walk our listeners through your career journey and what led you to what you’re doing today?

Yeah, for sure. So I’ve been fortunate to have been in a kind of B2B, VC-backed space for over a decade now. I started back in 2014, have worked at numerous Series B companies. I’ve worked at Series A, I’ve worked at the seed stage, and been a part of a couple of exits in the nine figures, one 10-figure exit, which is really exciting.

And you know, along the journey, I would say the through line has been taking on more interesting, larger upside opportunities. More risk, obviously, kind of with that. But yeah, finding challenges that whether it’s a more complex product, a more dynamic space, a bigger role and responsibility, that’s always been the driving force for me.

There have been numerous times in my career where I had success and could have chilled it out and coasted for a bit, but there was something in me that was just really hungry for that next growth opportunity. And I’d just sort of throw myself into these situations where I had no other choice but to figure it out, and it’s worked for me so far.

Yeah, very cool. I’m actually looking at your LinkedIn, and just to be fully transparent and also to show the vulnerable side of each of us, and to amplify that, so you started as a legal intern. So curious, moved away from the legal world into sales?

Yeah, that’s a good question. So in college, I studied politics, philosophy, economics, and law, kind of like a fusion degree. So my dad’s a lawyer. I thought that law was the career track for me.

I don’t like school. I don’t enjoy that model. I wanted something that was a bit more dynamic from the get-go, and so I stumbled into sales, as frankly most people do. But yeah, it’s been a journey so far.

Yeah. And then your first sales job was as a senior or inside sales rep at Main Street Hub. So talk to us about how you like it, what you enjoyed about sales and being in the inside sales world?

Yeah, the description I always like to use is, you know, everybody has obviously seen the movie The Wolf of Wall Street, right? It was like that, except for, like, nobody was making that money, obviously.

But no, it was just an environment where you picture like an old-school boiler room situation. You’ve got 100 sales reps on a sales floor, everybody cold-calling local small businesses trying to get $300–$400 a month subscriptions for a social media management system.

And these are small business owners, right? Like people who have a ton of responsibilities and pressure and stress, and you’re cold-calling them to try to sell them something. Like, if that doesn’t demand more out of you and force you to grow and build a set of skills, then I don’t know what does in the sales world.

And so I think what I just enjoyed about it was, number one, human psychology is really interesting to me. Like, I always find that, and I can talk at length about human psychology and why that’s sort of interesting to me.

But I think what it also scratched for me was the kind of competitive itch where it’s like, okay, if I do these things and I apply myself, I could do this really well. I could have success. And I could also have tangible success that, you know, relative to other people, like, this is something I could really do.

And so the competitiveness, the psychology aspect of it, you know, things are always changing. You’re meeting new people, you’re doing deals, you’re seeing the impact your solution is making on a customer, how it’s potentially getting them new customers or winning back existing customers, and seeing the degree to which it makes that impact too.

It’s all those elements combined that sparked something in me that said, you know, there might be something here. Let’s explore this further.

So inside sales is super hard, especially cold-calling, and that too to small businesses. It’s super hard, first of all, to get them on the phone. And if you do get them on the phone, it’s super hard for you to want them to take action towards your product or services.

So any secrets or any lessons that you want to share with our listeners for that?

It forces you to get crystal clear, back to the point of view, on what your value proposition is. And so I think some of the things that we see today, understandably, are a lot of people over-indexing on talking about product, talking about product capabilities and features.

And I think that’s all well and good, but at the end of the day, it’s like, what’s in it for me? Who cares, right?

And so when you cold-call a small business, you have a few seconds to demonstrate really quickly: you’re credible, you’re clear, you’re compelling, and you’re conveying a message that says, “You have this pain point today. Here’s why that matters to you. Here’s how I can help make that go away. Here’s how fast I can do that.”

Nice, yeah. So spot on. A lot of folks in the go-to-market world try to boil the ocean, and they try to cram in as many things as they can, versus forgetting the first principle, which is: how do you want the person on the other side to take the next step with the smallest friction possible?

Exactly, exactly. It’s a game of inches. Like, I use the analogy in football, any given interaction, just get the first down. Yeah, don’t get a touchdown, just get the first step. Exactly, move the chain.

Yep, so spot on. Great. So, Max, you moved from inside sales to account executive. So talk to us about that journey and transition. How was that like?

Yeah, you know, realizing, okay, I liked sales. I wanted to get more into a bit more complex, more enterprise-oriented software sales. And so those were some of the steps that I took after Main Street Hub.

And that was an interesting experience in that, instead of more local small businesses, these were more complex enterprises that had multi-stakeholders in play. So in some instances, it’s a committee. There’s also a question of the evaluation process and running trials or POCs, and ensuring that you’re back to the kind of question about value and messaging and clarity. There are multiple levels of that once you get into complex B2B, right?

There’s that for the user, there’s that for the middle manager, there’s that for the executive. And so, how are you tying those threads together and delivering a compelling value proposition for those customers? So there were a lot of learnings there.

Yeah, definitely. That’s a big shift, right? Selling to small businesses is one thing, versus large accounts and enterprises. As you correctly said, it’s like a buying committee. Plus, you need to hone in on the champion on your behalf, your partner within that account.

Yeah, a lot of learning, a lot of challenges. That’s a big shift in itself. But then, somewhere along the line, and after that, clearly, you’d done that role and moved into a sales leadership role. So, how was that jump like, and how did your management team actually get the faith, or did they feel okay, Max is the person to lead and build a sales team?

Yeah. So I definitely subscribe to the idea of leading by example. Like, I always try to have the mindset of “do the job.” And imagine you have the title of the role that you want to be doing. What would that person do? Okay, do those things.

And then eventually people realize, “Oh, okay, this person, you know, seems to be pretty equipped and qualified to do this next level.”

And so I think the mentality that I had is and part of why I’ve been oriented more towards early-stage, earlier companies is, you know, being like the first or second salesperson early on, demonstrating that I have a grip and a handle on the business, on the sales process, but then can extrapolate and have a point of view on the actual go-to-market system: the competitive dynamics, how to build a team, positioning, how to coordinate with the marketing function, the product, engineering, how to orchestrate across all of that to back to our original point wildly successful customers, sustainable, predictable revenue, that is predicated on a clear and compelling founder-led point of view and product experience.

And so I think the kind of short answer to your question is: coming in early and showing receipts, and showing that not only could I do what I was entrusted to do, but I had a plan to do something bigger.

Yeah, for sure. But clearly, you would have had doubts, doubts about your own capability. So talk to us about what those doubts were, and how you actually overcame those as you grew in this career?

Well, I think that for me, the doubt is always, it needs to be there. Yeah, it’s healthy, it’s stimulating. I think in every phase of my career, I’ve had doubts, and I think to me that indicates that I’m going in the right direction.

Because if I had no doubts, that probably means I’m not growing. So a doubt is a leading indicator of, okay, there’s room to grow, there’s room to learn, there’s room to expand who you are.

And trying to first reframe it that way, that, yeah, you’re trying something new, of course, you have concerns. Yeah. But the only answer to responding to doubt, which never goes away, is just taking action. It’s only through jumping in the pool and swimming, not by reading a bunch of books about swimming or stepping back and analyzing the pool, that you’re gonna get rid of those doubts.

Yeah, for sure. In fact, the term I was looking for, I couldn’t quite get the term back then, it was imposter syndrome. Yeah, let’s call it that, right?

Am I the right person for this job? Am I faking my way? Yes. Will I succeed, or won’t I? Will I let people down? All these are questions that will keep popping up, especially if you are that go-getter and ambitious person who’s looking to go to the next level.

Exactly. And I think the other thing too is, once you realize that the most successful people that you ever knew have felt the same way and often still do, I think it’s also massively reassuring that, hey, doubt is just part of it. That’s just part of the price you pay.

Yeah, for sure. All right, now let’s get even more real. This was real enough, but even more real when it comes to the tactics and strategies when it comes to go-to-market.

Yeah, so I ask each and every one of my guests two questions, right? One is a go-to-market success story. Another is a go-to-market until recently, I was calling it a go-to-market failure story, but I’ve shifted, and I’m calling it a go-to-market pivot story.

So I’ll leave it up to you, Max, which one do you want to start with, either a go-to-market success or a go-to-market pivot story?

I think it might be interesting to combine the two, because I think there are elements of both in this story. And the thrust of it is, we were at a point at Brightwave where we had a go-to-market system that was largely running on a typical kind of enterprise sales playbook.

Where we would get in front of a customer, we would do, obviously, a thorough discovery. We would move into some kind of technical validation stage, a demo, then some kind of POC, and then onboard them as a customer, etc, etc, etc.

And while that was, you know, working to a degree, there were a lot of challenges we were experiencing, and it was based on what I think were assumptions that we held that maybe we hadn’t examined recently.

And I’ll make that more explicit. What the world of AI has done is it has accelerated development massively, as we all know. And what becomes, in my opinion, the number one moat or differentiator today is the feedback cycle rate, the ability to test, get information, and then adapt really quickly. Because everything else erodes.

And so one of the things that we encountered or realized was:

1. We’re not getting enough information fast enough to make the product that we want to make and to acquire the set of customers we want to acquire.
   
2. The way in which we’re building this product, there seemed to be some incongruencies between that and the go-to-market motion that we’d been executing on to date.
   

Meaning, the product itself is back to POV, founder-led vision. Our founders come from an engineering, technical, visionary background, and they are absolutely clear on the future of what our product really is.

Simply put, it is a system that is able to reason across a large number of documents, pull out the factors that are relevant to an investment professional, and then turn those into high-quality outputs orders of magnitude faster than they can do it manually or with ChatGPT. To get to a conviction faster. So it’s a massive time-saving productivity boost.

And the vision that they have is that not only should this be a powerful, comprehensive system for complex knowledge workers to reason across documents, but also that it should be delivered in a delightful customer experience. It should be a UI/UX that is effectively consumer-grade.

And so if we’re building that, and we’re executing on an enterprise sales process that traditionally gates the product, holding in reserve our biggest differentiator, that’s a mismatch.

And so we restructured our system to align with the incredible rate of development and shipping that our engineering team has been doing. Such that, you know, we say, okay, a product like this if your prior mental model for something like this is like ChatGPT, and I come in and say, “Okay, so Vijay, it’s gonna require a few weeks of onboarding and consulting,” and you’re like, “Dude, I can get ChatGPT in 30 seconds. What are you talking about?”

It’s got to be easy to get. It’s got to be easier to use.

And so now we’re redesigning our process where we’re front-loading the product experience, getting it into the hands of users faster. Because, by the way, we understand to a tee what workflows our users are using Brightwave for to drive productivity.

So it’s just a matter of getting to those people as fast as possible and letting them experience this as fast as possible.

And then what we’ve seen since we’ve made this pivot is, as you can imagine, 3x user adoption. Hearing stories like, for example, “Hey, this saved me days on this process that used to take me,” or someone literally showing us relative to ChatGPT or a competitor tool, “Here’s how it took a process that with one person plus all the consumer LLMs took me hours, and I brought that down to minutes.”

So it’s a tsunami of information that we’re getting to make the product even better and capitalize on our competitive differentiation, which is this consumer-grade UI/UX and our competitive wedge at the moment.

Yeah, that’s a great story for sure. Feedback, one thing that I took out, the keyword is feedback. Feedback from the customers, from the market, back to the product how to make it easier and front-load the onboarding and user experience.

So that’s one thing that I’ve heard, which translates to the KPIs around user adoption and maybe testimonials. So I’m just curious how that is helping in your sales, in your go-to-market? How is that playing out?

The result has been that when I say 3x usage, that’s obviously translating into revenue, right? And that’s translating into people who are now on the platform, who are using it, who are getting success.

We can repurpose those testimonials. The greatest sales asset that exists is a customer story. “Don’t take my word for it, listen to what your peer said.”

Maximizing that, maximizing early cohorts of super successful users who will go evangelize us, who will help build our product even better. It’s accelerating distribution, it’s getting into the hands of more customers, getting more sales, getting faster time to adoption, and then upgrading.

So to me, the go-to-market system is not just, “Okay, how many logos are we getting, and then what’s our revenue?” It’s like, hang on, let’s take a step back for a second. How many people are using the product? What are the usage measures? How successful are they in using it? How fast are they expanding?

How many sessions, or how often are they coming back? How quickly are they expanding? How quickly can we get in the door with some of these customers? So, really exciting stuff, and with the information that we’re getting.

Yeah, very cool. And then coming back to your title, you mentioned it’s Head of Go-To-Market. So what does that really encompass? Does it even include marketing aspects and customer success, or is it just different functions within sales?

Yeah, so we’re, you know, we’re a lean team here. And so it covers everything around customer success, marketing, and sales. And again, you know, I think sometimes those terms and those barriers are artificial and unnecessary and counterproductive.

It creates this sort of like, you know, marketing versus sales versus customer success, when in reality, it’s like different flavors of the same thing, right? It’s, how do we get this sustainable revenue model and wildly successful customers, and how do we figure out spheres of influence to maximize that?

Yeah, for sure. And that’s one thing the origin of this podcast was all around that central theme, which is: when you talk about go-to-market, it has to encompass marketing, sales, customer success, and product.

So for me, it’s all those four functions that are what go-to-market is. And so that’s my little pursuit, yes, through this podcast: to bubble up that message, amplify it, and spread that message.

You can ask my team. I don’t know if there’s anybody in my company who’s in Fireflies more than I am. Fireflies, full story meaning, you know, user sessions, and user log data. Like, I’m addicted. It’s like watching Netflix, you know, seeing… so I totally agree.

Great story, great go-to-market success, and a pivot story. So just curious want to extract. Clearly, you had a wealth of knowledge when it comes to sales and go-to-market. So if you can share one more, either from Cutover or Looker, that’ll be great. That’ll be more in the sales domain.

Just a general nugget, or general kind of I think, you know, how I try to be effective is I always come back to the acronym KYC, which is the financial, cybersecurity model.

But the bottom line is this: to the degree you know your customer, yeah, intimately.

What is their day-to-day? What are their KPIs? What gets them promoted? What gets them fired? Where do they sit in the organization? How would they use their product? What are their pain points? What are the stories you can bring that will resonate with them?

If, as a sales professional, you started at a new company and the only thing you did was just spend hours and hours interviewing your prospects, I guarantee that within a few weeks, a few months, a few quarters, you’d be the top person at whatever company you work for.

And understandably, there are so many forces that are conspiring to obfuscate that very simple truth, know your customer. Because when you know your customer, you know how to position. It sharpens your own point of view on the problem that you’re solving. It creates this virtuous feedback loop that makes everything much easier.

Yeah, for sure. I’m actually glad we took this conversation down this path. “Know your customer” is so super, super important.

Going back to the whole definition of go-to-market, yes, having a point of view is important, and having a predictable and scalable revenue path is important. But it all starts with your customer. It starts with who your customer is, what the challenges are, and what the struggles are with their existing solutions that are out there. That’s where it all begins.

So curious, if you can expand on maybe rituals or tactics, go about really knowing, like, pick one account as a hypothetical example. How do you go about knowing your customer?

What’s great with AI now is the rate at which it is actually now it’s like, there are no excuses. Before you step into a meeting with a potential customer, and you don’t know… now it depends, obviously. If they’re publicly traded or private, that limits the amount of information.

But what you can get with AI tools to understand:

• Who are the competitors?
  
• How do they make money?
  
• What’s the organizational hierarchy?
  
• What have been some recent events that they care about?
  
• What are some strategies or priorities that they’ve made public to the company?
  
• What is the background of the individuals at the organization?
  
• What’s their familiarity with different technologies, solutions, and problems?

And understanding: okay, so how do I then map that to stories, to solutions, to success stories that I can share with their peers are and what their peers are doing? Because that’s the first thing that people want to know: what are my peers doing? How do they see this?

And knowing that, and then mapping that to what their peers are doing, even if you don’t even talk about the product. Just show up, know who you’re talking to in great depth, and share, based on that, the success stories that are most relevant.

I’ve seen people do that basically, that’s all they do, and they’ve been wildly successful as sales professionals.

Yes, yeah, for sure. Let’s get even more tactical, at a five-foot level. How do you go about getting that first meeting, getting that attention?

Yeah, so I think it is massively contextual. Massively contextual.

Okay, if we’re selling something that is, let’s say, we’re selling to a large financial institution. Let’s say we’re selling to J.P. Morgan Chase, okay, and we’re selling a probably six-figure or seven-figure software item.

What’s probably most likely, and again, to go even more granular, the question is: is it something that’s more of a top-down sale? Is it more of a bottom-up sale? Is it a product that you can get into the hands of more executor-type workers and then work your way up?

So I would say it starts with: what’s the product I’m selling? What’s the value proposition for each person?

But the TL;DR is you develop a point of view on the problem space, what’s happening at your company, and your solution set, your success stories. Map that to the organization that you’re working on. So: what are they trying to optimize for? What are their pain points?

And you generally want to do that at the level of executive, middle management, and user.

And then from there it’s: okay, what’s the most effective way to get that person? For example, if it’s a developer, cold-calling might not be the most effective way. Maybe it’s Reddit forums. Or maybe it’s certain events. Or maybe it’s sending over a sample of your product, for example.

Whereas if it’s a managing director, probably more high-touch. Maybe a personalized outreach from somebody on your board who might be connected to them. Or maybe it’s trying to curate some kind of small dinner gathering where you invite them and you invite some of their peers who are your customers, right?

So, the short answer is: depends on the context.

Exactly, yeah, for sure. The way I’m looking at it is essentially: draw your account map, the people that you are trying to tap into, and the org structure. And then, depending on the level of seniority as well as the background, what is the right channel and engagement model? How is that going to happen?

Exactly.

Exactly, yeah, for sure. The way I’m looking at it is essentially: draw your account map, the people that you are trying to tap into, the org structure. And then, depending on the level of seniority as well as the background, what is the right channel and engagement model? How is that going to happen?

Exactly.

Yeah, for sure, very cool. So this has been great stuff overall, Max. Let’s take a step back what have been the resources or communities or books or podcasts that you’ve been leaning on heavily, that have really upped your game?

Yeah, so this is gonna sound maybe unusual, but I try to balance domain-specific resources with totally non-domain-specific.

I’m a big believer that there are patterns everywhere that very much transfer into domains that seemingly make no sense. Something that you might see in a biologist’s mentions might actually have something to do with sales. Something in some weird, obscure theory in physics applies to fitness.

Whatever the case, I read and study widely and broadly whether it’s podcasts, books, or conversations with people. I love learning about new areas, new domains, and new niches of knowledge.

Because if it’s good, it probably is a pattern that I can apply and test in my own domain, right? So that has been effective for me.

Because I think and I’m sure you know this, obviously, sometimes when we just stay in our own niche, our own echo chamber, we get stuck in these frozen mental models, yeah?

And frameworks and playbooks that we just sort of take as like capital-T truth. When in reality, those are artifacts of a time and a context and had use, but they’re not eternal truths, right?

So back to feedback cycle rate: finding new ways of thinking, new mental models, new frameworks, new playbooks, trying them out, seeing what happens. I think taking that broader approach has been really useful for me to avoid being rigid in my thinking.

Fantastic, yeah, always looking to learn, and looking at complementary (not complementary) topics that are outside of your regular day-to-day work. I think that’s super, super critical.

For sure. Again, very few people must have played a key role in your career growth played like a mentor, along the way. So any specific people who come to your mind who have shaped your career?

So I’m gonna cheat a little bit. One, I would fuse both my parents together as a first bedrock. Yeah, just immensely grateful for what they afforded me in so many ways growing up, and just as role models. More in what they did than anything else, right?

I think people, it’s more about leading by action and leading by example.

I think another, professionally: my first manager, my first boss at Main Street Hub. His name is Darren. Was somebody who, again, taught me a lot more by what he did and how he was than anything else. I continue to be he’s close friend to this day.

And somebody who, I think a lot of the time, is people who maybe see more in you than you see in yourself at a given time, or awaken something inside of you that maybe you hadn’t been acquainted with yet.

I think those are the interactions and the role models that helped most. So I think that was one as well.

And then, you know, I would say more recently, my current boss today, CEO of Brightwave, Mike, is somebody who obviously took a chance on me to lead the go-to-market organization of Brightwave. And has inspired me with a lot of confidence in my own ability to shoot further, you know, and be more.

And I think those types of figures throughout my career, throughout my life, have been absolutely critical to my own development.

Sure, yeah. Those are the critical components in our lives, right? People who have really touched you, actually invested their time and energy. And as you said, right who believed in you even before you believed in yourself at a certain stage.

Yes. Sure. Yes.

So what are those one or two skills that people really look up and say, “Hey, you know what? We are struggling in this specific skill set, maybe it’s go-to-market or sales or expansion, whatever it is, we need to go and talk to Max.” What are those one or two skills?

So I think there’s the micro and the macro.

At the micro level, over 10 years, I’ve seen almost every permutation of a B2B sales cycle. You know, getting a deal from point A to point B, call me. That’s something I’ve developed, and is obviously a strong suit.

I think the second, more macro, is what I’ll call “go-to-market system intervention.” Because I’ve been in a number of different environments, contexts, seen what’s worked, what hasn’t, I think I’ve developed a pretty sophisticated pattern recognition where I can get a sense, a feel, a taste for what are all the processes and flows in a go-to-market system that, to your point, include sales, marketing, customer success, product.

And identifying the highest-leverage intervention points, taking action, running experiments, and getting different results is also something that has developed over time. So there’s the micro, there’s the macro.

Fantastic, great. Final question to you, if you were to turn back the clock, what advice would you give to your younger self on day one of your go-to-market journey?

Yeah, good question. I would probably say a quote, which is some version of: reality is responsive. Reality is malleable. Action generates reality.

Right back to what I was talking about earlier, around the swimming pool example. Things are not fixed and final. Things are in flux, right? Who you are, what things are don’t discount or say, “That’s just the way it is,” or, “That’s just the way that I am.”

The only way you know limits is you have to taking action, running experiments, and bumping up against those limits. And we all know intuitively, we are operating at a fraction of the capacity that we could be operating.

We know we’ve seen other people, and we’ve experienced this ourselves. How we’ve taken action, we’ve made commitments, we’ve taken steps, and all of a sudden, reality is reconfigured in some way, right? Nobody else can tell you that. And no amount of thinking or strategizing or advice that anybody gives you is going to change that fact.

Yep, for sure. And that’s a great piece of advice. That’s something that I keep reminding myself it always boils down to: what is the smallest next step and action that you can take? You’ll be surprised so many times.

In my own experience, I’ve seen with others as well, I’m sure you can relate to those as well, Max, which is that you will actually surprise yourself, yes. And you’ll wipe out or rewire your belief that you had after you’ve taken that series of actions. Yeah, it’s incredible.

Use cases, not just features.

That’s how Simon Ooley, co-founder of Veles,  a YC-backed startup reshaping how enterprise sales teams engage buyers, and former sales leader at Procore and Builder, reframes the future of enterprise sales. Instead of selling products, he helps teams sell outcomes—anchored in urgency, ROI, and the real problems customers are trying to solve.

In this episode of the B2B Go-To-Market Leaders podcast, Simon joins Vijay to unpack his journey from BDR to founder and YC-backed entrepreneur. 

They dive deep into:

• Why traditional sales roles are merging under the GTM umbrella

• How can large teams eliminate inefficiencies in quoting and deal desk processes?

• The power of use case-based selling to drive urgency, personalization, and long-term customer success

Simon breaks down why founder-led sales isn’t just about hustle, but about curiosity, experimentation, and relentless clarity on what your buyers actually care about. You’ll learn how Velus is shifting sales conversations from product features to business cases—and why that shift might be the most important evolution in GTM strategy today.

Whether you’re scaling a sales team or starting from zero, this conversation is packed with tactical insight and a whole lot of heart.

Connect with Simon Ooley on LinkedIn:
https://www.linkedin.com/in/simonooley/

Connect with Vijay Damojipurapu on LinkedIn:
https://www.linkedin.com/in/vijdam/

Listen To The Episode:

From BDR to YC Founder: Simon Ooley’s GTM Playbook for 0 to 1

 I always open the show with the signature question, which is “How do you view and define go-to-market?” 

Yeah, I’ve enjoyed listening to your podcast, and I enjoyed how your guests have defined this.

I think I take a slightly different approach to go-to-market than some of your other guests. I think the go-to-market, in general, is expanding every day. It’s eating up more and more of the revenue life cycle and everything that people define as marketing, sales, rev ops, et cetera.

I personally define it as, and our business looks at go-to-market as how we show up to our customers. And that is defined, how do we show up as a digital presence? How do we show up as a partner, an implementer, or a vendor? And so we think about go-to-market as how do we show up to those organizations, and what are our use cases that we’re driving for with those customers? So I’ve even expanded the definition. 

Yeah.

So I guess I’m a culprit there as well. 

No, this is all good. I mean, that’s the fun thing about this topic, go-to-market.

I mean, I was just quickly looking at my podcast history before jumping on this recording, and it’s been going on for four years. I’ve been, I’ve had the good fortune of talking about go-to-market for over four years. And here’s the funny part, right? Go-to-market, the definition is, as you said, it’s constantly evolving, it’s expanding.

And for me, it’s like any software product. I mean, you have a V1 or V.5 and it has to evolve. And the same thing goes with go-to-market.

It has to evolve, not only as a broader definition for the industry, but even the go-to-market for an organization will evolve based on so many factors. 

Absolutely. Yeah.

And we’re in the midst of the GTME kind of movement led by Clay and some other businesses that have, I think, expanded that or sped up that evolution quite a bit. 

Yeah, so just curious. I mean, this is something. When I started the podcast, this was about four years ago. Back then, GTM and go-to-market were not such a big term or not, as popular as it is today. But just based on that one line you mentioned, I’m curious. I mean, for me, it’s more from a curiosity point of view, like how and why do you say like the GTM concept has, is more popular now with companies like Clay and others? 

Like, I just want to get your take on that.

Yeah, I think it’s Clay for one, who we’re a customer of. We love working with Clay. But even if you look at OpenAI’s roles, if you look at Anthropix’s roles, like there are no salespeople.

Yeah. 

They don’t have an account executive as a core job title anymore. It’s just GTME.

And so, or GTM, excuse me. GTME is maybe a little bit more Clay-specific. But I think one of the reasons for that is organizations are starting to move more towards, I think, this is like kind of forward deployment type model.

They’re looking at, hey, we’re going to bring on a customer, but our sales team is not just going to close the deal and kind of throw the grenade over the fence to customer success and say, good luck, go and implement that business. Which I think traditionally in kind of 2014, when I started in sales through to the, like 2020, that type of timeframe, there was a lot more of that segregation of those roles. Now it’s becoming far more integrated.

And so I think instead of saying sales, marketing, customer success, I think go-to-market has just kind of swallowed up all three of those functions. I’m happy about it because I think it does turn the focus back on the customer and say, How do we take you to market? And it’s not, how do I get a deal done and get commissioned as a sales rep? And it’s not, how do I implement this customer as an implementation manager? And it’s not, how do I make this customer successful as a customer success manager? It’s like, how do we just take you to market? How do we make you successful as a whole? 

Yeah, no, it’s actually interesting. And on a different note, funny as well that you say that and how you define go-to-market, right? So couple of years ago, even a few years ago, and even like a few guests on this podcast, when I talk and ask about go-to-market, especially if they’re from a sales-centric background, they’ll say go-to-market is sales and sales is go-to-market, period, right? That’s a very narrow view.

And then over time, it expanded to include marketing and, of late, customer success. But there’s also one more leg, I mean, a critical lever. How about the product? I mean, if it’s not product slash service, you do not have a winning go-to-market.

Absolutely. I mean, the product is, you know, as a founder now, and I’ll give you a little bit of context on my background. I came from sales.

I was all in like an enterprise quota-carrying sales rep for many years. I either was a quota-carrying rep or leading a sales team for a decade. And so I was always working with the product.

Product was always my better half as it relates to how I win a new business and a new market, and a new region. They were the ones who actually, you know, facilitated me being able to close a deal. So they started to become the backbone of everything that go-to-market really does.

I mean, the product is building what you are going to market for your customer to solve. And so they are the core underpinning, but a lot of people do forget that like product is part of go-to-market. 

Yeah.

They are the core piece. 

Yeah, absolutely. Awesome.

I mean, this is a great start. Let’s double-click into the topic you just ended your conversation with, which is your career. So why don’t you walk us, walk me and the listeners through your overall career journey, how you got started in your professional life, and what you’re doing and what led you to what you’re doing today? 

Yeah, it can be long-winded, so I’ll do my very best to be concise.

But I started my career in SaaS or software in 2013, 2014 as a BDR. That was my first job, straight out of it, and cold calling. I actually call that the Zerp era of outbounding.

Sure. 

And I think a lot of people would agree that it wasn’t just the Zerp era of dollars and capital, it was also the Zerp era of outbound. You could send emails, and people responded, and you could increase the volume of that and equally increase the response rates of that.

So it was a great time to be a BDR, but I absolutely fell in love with sales at that point. I had about a year and a half of being a BDR. I identified that there was an area of the business I was in that was underserved, which was the international markets, Asia Pacific, and the UK.

And I was lucky enough to be at a super fast-growing business that was Procore. And the reps at the time were like, they were doing great. They didn’t need to be taking on more deals after hours.

They didn’t need to be taking other accounts. So I basically went to our CRO and I said, hey, I’ll be BDR during the day, let me run some deals at night. And I think as a CRO, having an employee come to you and say, You don’t have to pay me anymore, but I’ll do more work.

That was an easy yes for them. 

Yeah. 

And so I was able to do both roles, teach myself how to sell.

Fast forward, we went from zero to about 1.5 million in the Asia Pacific region for that company. And we were really lucky to start building out that team while still being in the U.S. Flew out there, opened an office in Sydney, Australia, and the Procore. And we were really lucky in the three, three and a half year span that I was involved with that team to get to about 10 million in ARR and a 70-person kind of boots on the ground office, which was a fantastic journey.

I got that like that bug of building things. Even as a seller, I was quota carrying, but I was kind of leading that team, hiring people in every division. And so I came back, and I was absolutely fired up to build things.

So I asked myself, could I do that with no money? As an entrepreneur going, opening a new office, you’re not exactly strapped for cash. So, you know, you can pay for a big, we work, you can take people out to dinner all the time. And I wanted to challenge myself to do it without money.

So I joined a bootstrap startup as the first non-founding employee, and we were incredibly fortunate. And I was hired on by incredibly smart founders, but we were able to do it in a very similar timeframe, about 3 million in ARR with zero capital invested in the business. And so those two experiences really drove me to want to be a founder, but also in that same vein, we were experiencing so many challenges around pricing and packaging, around the quoting process.

How do we streamline this for large teams? And then also for small. And so it really led me down this path of building a better solution for not only pricing and packaging, but just the rep experience as it relates to product and price. And that’s what drove me to found Belus.

Very cool. Amazing story. I mean, starting off as a BDR and a lot of people get stuck at the BDR stage, and the luck if you go to the next stage, which is the AE, but for you, I mean, it’s not BDR AE, you went further and way beyond.

And that’s the proof point as to why YC actually accepted you in the first place, right? You’re not just a, hey, I’ll do my job, and I do my job, and meet my quota, and that’s it. So it’s that hunger, it’s that curiosity, and the passion to learn is what I’m sensing throughout, and also knowing yourself in the process. 

Yeah, absolutely.

I mean, I think I came to this concept of like, I think my wife calls it aggressive learning. I get really passionate about a subject, and all of a sudden, I have every book on Amazon about that subject being ordered to my house. I wasn’t an incredibly good academic student.

Early on, I didn’t quite see the value in the syllabus, and if it didn’t immediately engage my mind, I probably failed the class. But I learned that later on, I absolutely got fascinated with how to be better at any specific thing I was doing in the work environment. And so, yeah, I think being really curious is probably the best thing that you can do as an early employee at any business.

Find all the problems and be the solution, and you’re going to go the right way. 

Absolutely. I mean, that’s a key thing that you shared, right? I mean, academic performance and doing good in a school or college environment is one thing.

And similar to your story, even I was not good academically because it’s almost like it’s being pushed onto you, versus later on in my life, I realized, hey, I’m interested in this topic. I want to read more or dig into it more. And by the way, this podcast was started from that hunger and curiosity.

I mean, I want to learn more about go-to-market, so why don’t I start a podcast and in the process, share my learning with the broader community? Absolutely. That was a thesis.

So fast forward to, I think, 2024. In fact, I can take this conversation into so many areas. Let’s actually, I’m looking at your LinkedIn profile and looking to see which one to dig into.

So, talk to us about the builder phase, where you are like the founding salesperson, founding a GTM ad builder, because as you correctly said, having the luxury of a budget and a big brand like Procore is one thing, and building internally within that. But then at Builder, it’s not zero budget, but very close to it. I’m assuming it’s just one.

So talk to us about that. The reason why I’m wanting to go down this path, Simon, is that a lot of the listeners are founders as well. And so for them as founders, how should they do founder-led sales, or in your case, very close to that, ad builder? 

Yeah, I think it’s really my experience at Builder, and the founders will probably listen to them and reminisce about how scary it was.

But we were an early-stage business that was just starting to gain momentum, product market fit, and getting really excited about the future, right as COVID kind of completely shut down the construction industry. For those of you who don’t know who Builde is, what that company does, they’re a CRM for construction companies. 

Got it.

And so very adjacent to Procore, I think there are a few great learnings we had working alongside a big organization like Procore. And it’s a really great go-to-market strategy if you are adjacent to a large player to be able to really draft off of their success and use that as a go-to-market lever and channel to grow your business. But I think my time at Builder was unique in that COVID hit, and no one knew what to do from a construction standpoint.

Do we send people to a job site? Right. Does our $4 billion a year business just halt and freeze? And what do we do with that capital? What do we do with the job sites? It was a very scary time. I think something that I learned early on is that creativity is king as it relates to go-to-market when you do not have money.

That is the core thing that I learned there. And it was a testament to obviously, the founders who were incredibly creative, but also their ability to just give me leeway to try things. And so early on, some of the things that we focused on were just how do we just make construction people’s lives easier in this crazy phase of life? The PPP loans came out, no one really knew what was happening, and there was like a bucket of cash that was very quickly being sucked away.

And so one of the things we did was just dove incredibly deep into that and wrote up a whole website on how construction organizations should be able to interact with the PPP loan. And I don’t know if that directly correlated to revenue in the door, but I know that all of our customers and all of our prospects thanked us for just doing that work upfront. And so for any founder or early stage sales team that is working at a company that doesn’t have a lot of resources, that can’t spend thousands of dollars or tens of thousand dollars a month on ads or paid advertisement, you just have to be really creative and hungry and just put things out there that are unique and that are fun to do.

Because if you’re not having fun doing early-stage outbound, early-stage kind of marketing, or the umbrella of go-to-market, you’re gonna struggle. You kind of have to just play around, have fun, and figure out what’s gonna work. 

Yeah.

So that’s a great insight, right? In  COVID times, especially in construction, it was not clear whether the construction management as well as the team, and the labor force, how that would pan out and for how long. It was a big unknown. And what I heard you say, Simon, as the team at Builder and you latched onto PPP as a wedge to deliver value to your ICP and target audience.

Absolutely. It was one thing that no one knew anything about, and everyone was trying to figure out how to survive. 

Yeah.

So that was something that we latched onto. I’d also say that there was something awesome, Vijay, in that specific phase. Our ICP was a large enterprise construction.

So there is a report that ENR, as an organization, puts out every year, the ENR 400. Like the top 400 construction companies by what’s considered annual construction volume, the amount of construction they do per year. And so those were our key customers.

Most of those businesses were a hundred years old. Like they’ve been around the block. 

Right.

And so we actually went to them and said like, Hey, what do you do in this type of situation? And most of these large enterprise builders, they’re like, hey, this isn’t new. We’ve experienced things like this. We may not have experienced COVID, but we’ve experienced these moments of uncertainty.

Correct. And these are the opportunities for us to take advantage when no one else wants to. Nice.

Warren Buffett said, “When nobody’s buying, that’s the time to buy.” When everybody’s selling, that’s… So I think construction took advantage of that. And so we were able to learn from them and also partner with them in that kind of uncertainty, which was another great play for us.

Understood. And how was the outbound like over there? Like you must have done clearly, I mean, a lot of outbound in addition to putting together all this content, like how to use PPP. So, just walk us through a one-minute spiel on our overview of the outbound.

Yeah. So, I mean, I come from, again, the Zerp era about outbounding. So I’m a cold caller kind of through and through.

And I think when we were at Builder, like email was becoming less and less of a viable outbound option without that connective, like cold calling. So I think there are a lot of fantastic people out there now talking about how to still do outbound, but the 30 NPC guys are great with their outbound cold calling sucks book. I think it’s absolutely true.

But cold calling is still, I think, the best way to reach people is to get on the phone and have a conversation and be a human being. And so at Builder, that’s exactly what we did. I think we’ve also had a great partner in Procore in being able to draft off their success and engage with their client base.

Yeah. 

And in-person events for construction were also great. So we basically took a three-pronged approach.

We were a fantastic Procore partner, we did cold outbound, and we went to in-person events. And those were our three ways to really get in front of people and show them the value we could provide. 

Got it.

So, just double-clicking on cold outbound and cold calling. So did you have like an auto-dialer? I just wanna get into the tactics. Like, how did you really do that and when at it? 

Yeah, we didn’t do parallel dialing at that time.

I’m really, you know, I think parallel dialing is really exciting because you can just get so much more throughput. But I also am always hesitant about quality over, or excuse me, quantity over quality, is not always the right approach. And so at that time, I think, you know, we were on kind of the standard stack.

It was Salesforce, outreach. We had, you know, Zoom info, and we kind of just ran that standard play, but we just really approached the messaging with a lot more strategy, a lot more thought into that. We didn’t try and recreate the wheel as it related to the tech stack.

Got it. 

Those were tried and true tools, and we just kind of jumped on the back of those, and then really focused on how we get the message to the customer. 

Understood.

Very good. So, coming back to our bigger story over here, you did your thing, what you had to do at Builder, and then you got that founder, entrepreneur edge biting hard at you, and you applied to YC. So tell us about that story, and how did that came about? 

Yeah, so my co-founder and I both worked at Procore together, and we knew we wanted to found a business together.

It took us a lot longer to finally bite the bullet. So hindsight’s 20-20. We probably would have started it sooner, but we threw our hat in the ring for YC with the expectation we would not get in.

I think everyone probably does that because of their low acceptance rate. But I think we had a really unique story. We had some incredible proof points to say this was a real business, and we were building it as a kind of hobby until we realized this was an enterprise product we really needed to go all in.

Nice. And so we applied to YC. There are a million YC application stories, but it’s a very high-pressure time.

YC is all the YC group partners, and we were really lucky to have a great set of YC partners as we went through YC. They do not kind of beat around the bush. They’ll tell you exactly what you need to do to be better.

You only have three months with them, or even less. It’s such a short period of time that you’re actually with the YC partners. They just try and push you to be as good as you possibly can.

We applied to YC. We had a less than 10-minute interview. 

Sorry, just on that, so YC partner, is that the thing before applying to YC, or is it part of YC? 

So, yeah, so YC runs their cohorts.

You have group partners. So you have people who are working with you. And so one of those group partners is gonna choose your application.

Got it. 

And they’re gonna be kind of like raising their hand to say, like, they want you to be part of their group. 

Yeah.

And so, yeah, we applied to YC. We did our 10-minute interview. I think anyone who’s gone through YC knows that the interview is super high stakes, very scary, and super fast repetition questions.

Like you don’t have a lot of time to build rapport. That’s not why you’re there. And then that meeting ends, and you look at your co-founders, and you say, I have no idea how that went.

Yeah, absolutely. I think when we came out of that meeting, I turned to my co-founder and said, I ruined it. I ruined it.

There’s no way we’re getting picked. And he turned to me, he said, I think that went great. Okay.

And he’s always the more conservative of the two of us. So I felt, but it’s a very fun experience. I think everybody who has the opportunity to apply should.

Yeah. 

And the ability for them to really put you in a place to build and be creative is incredible. So it was a very fun experience for us.

No, fantastic. And I’ve had the good fortune of hosting YC founders in this podcast, but I think, not I think, I know for a fact, you are the first person who actually revealed a playbook that was not revealed until now, which is working with a group partner before applying for YC. 

Oh, I’ll correct you.

So our group partner, the first time we met him, was during that 10-minute interview. We didn’t work with any group partners beforehand. You can, I mean, I think this is super broadly known, but there are existing YC alumni who always post on LinkedIn pre-batch, like, hey, do you want to meet with me for 10 minutes and talk about it? I think I did that four or five, six times.

I talked to as many YC alumni as I could prior to going into that interview. But yeah, no engagement with the YC group partners prior. That would be awesome.

I would love that, but I don’t think with the engagement. 

I understood that. That’s what I was wondering.

I mean, is that like a prep school for YC, a formal prep school? Obviously it’s not there. 

No, definitely not. I think you have to be really innovative to get as much information as you can. But there, I mean, there’s 4,000 plus alumni. You can always get them on LinkedIn. 

Yeah, for sure. 

So the other question is, actually, let me hold on to that question because I want to dig into what you do with your start or what your startup does rather. And your startup’s name is Veles. So, tell us about Veles, who you serve, and what is the property you’re looking to solve broadly in the industry? 

Yeah, I’d love to, and I’ll keep it short because I really enjoy just talking about the tactics.

But Veles is basically an enterprise workspace for sales teams to bring together the real use cases that they’re selling, the pricing for their product and packaging, and the ROI narrative around that. So really trying to bring sales teams back to kind of first principles and basics and understand what the actual outcome is that your customers’s coming to you to solve. 

Right.

So we’re trying to move sales teams away from just selling the value language that is put together for the product or the bundle that they have to sell, and really trying to switch the paradigm to focus on what are you coming to us to solve? What are those use cases? And what is the offering that we can put together to solve that use case? And so Veles kind of holistically is a use case-based sales motion that focuses on an intuitive pricing and packaging, pricing calculator, and an ROI kind of use case builder that ties that fully together. Yeah, no, this is great.

So I just want to double click on what is your unique story? Clearly, there’s a unique story, and that’s why YC funded you, because I’ve had the founders of Aligned and the founder of Accord on this podcast. And just from a surface level, I’ve not done any deep research. From a surface level, there seems to be a lot of overlap because at the end of the day, you’re trying to figure out how you, as a seller, how do you work closely with your buyer and the buying team and then walk hand in hand, right? So I’m just trying to understand.

So help me and the listeners understand, like what is your pitch and the wedge that YC saw in you, and how you’re going to win at this? 

Yeah, I won’t speak for what YC saw in us because I think that’s still unknown to me. I appreciate the fact that they picked us, but I think, you know, I look at sales from the lens of why or what a customer is looking to solve. I personally don’t feel like any AI agent, any credit, any token, or any product bundle inherently has value to any customer by itself. 

Right. 

So if we think about it, I am selling 1 million tokens to a customer, 1 million tokens means really nothing.

It doesn’t have any inherent value until you associate those credits with a use case that the customer is looking to solve. And so if we think about sales in general, let’s just break it down into its kind of components, its basic layer. A customer is coming to you to solve a problem.

If there’s no problem, there’s no reason for them to be in this room. There’s no reason for them to have this conversation to do this demo. They’re coming to solve a problem, and that problem is your use case.

So it is not your product that is the solution, really. It’s you’re coming in and you’re solving a problem for that customer. And I think if you break it down to that basic layer, every sales motion will have more urgency.

It’ll have a higher value. You’re gonna be able to provide ROI to that specific problem in a way that is believable, not a grandiose 11X ROI on this, everything you could possibly do with my product. 

Right.

And so that’s kind of our unique edge is we’re looking at organizations and saying, hey, you have an incredible set of use cases that somebody would come to you to buy. Let us help you really clearly identify those use cases early on in a sales cycle and drive urgency value and ROI as it relates to each use case that someone’s coming to you to solve, instead of trying to approach everything as a one-size-fits-all product and packaging exercise. And it’s become incredibly valuable to not only help a lot of AI-based businesses, credit-based companies sell more, but it’s also kind of redefining how they deliver their offering.

I’m selling these three use cases. You can then take those three use cases over to customer success and say, these are the three things they want to accomplish with our product. 

Yeah.

They can go and deliver on those three things. And then you can come back together and say, hey, we’ve delivered on those three things. What else can we help you solve? What are the other pain points you’re feeling? And so there’s a much better identification of why it’s based.

There’s a much better way to upsell and cross-sell all of your products and packages when you’re focused on them. It’s specifically focused on what they need to solve. 

Yeah, totally.

I mean, this is one thing, I think that’s a key principle for any sales. And for me, just a side note. So I am like a strategic growth operator or a go-to-market architect where I work with these doing 10 million over, understanding their go-to-market challenges, and then putting together either a workshop or a proposal, or an engagement.

So, for me, very similar to what he just said, Simon, it is all about building a business case. So they are coming to me to solve a use case. And in my pitch, air quote pitch, I mean, for people who are not seeing the video, right? And a proposal, it’s a short proposal.

I keep it very intentionally. It has to be very short. It’s a two-pager business case.

And the first is around the problem set, why they came, and what is the problem that they’re looking to solve, the cost of inaction. And then there’s the pricing. What is the investment required to solve that problem, and what will they get once it’s solved? And tying the ROI, like either a three, five, 10X, whatever that thing is, is super critical for that buyer to champion your product or service internally.

And given, I mean, Zurb days, it’s way behind, but given today, where each and every buyer has to prove to their finance committee and the CFO, it’s super, super important. And that’s how I’m seeing connecting the dots based on what you just said, right? How are you helping the salespeople in building that ROI in a business case for the buyers? 

Absolutely, and to kind of tie it back to the first thing we talked about, where product is also a big part of go-to-market, when the entire organization turns and looks through the lens of use cases, it’s so much easier to identify which use cases apply to which customers. If a new business comes in and is asking for the same use case, the majority of your business is the reason why they came and purchased your product.

All of a sudden, you have the best reference customers, and you have the best ways to engage. Your product team also knows what use cases they’re coming to buy your product. That drives better product decision-making.

So everything is really tied around why somebody comes to your business. And I think we’re starting to see it. I went to an incredible revenue conference in New York recently called RevFest, and they’re gonna do it again next year.

So anyone who wants to go should definitely go. It was world-class, just one day. But I did a little bit of prep to meet all these companies that were going to this conference.

Out of all of these businesses, it was like 95, 96%, there were only like four or five companies out of the entire thing that I looked at, all had the concept of use cases on their website. So on their website, already, you go to the homepage, you hover over use cases, all these incredible ways that someone could use their product. But when you go into a sales notion with them, they’re like, Here are our products, how many users? They’re not pulling it all the way through, but we’re getting so much closer.

Use cases are the reasons why people come to your product to buy. And if we can have the entire sales notion that way, we’re gonna learn more, we’re gonna sell more, people are gonna be a lot happier, less churn. Every kind of main metric a business cares about goes up.

And so I’m really excited about this. I think it’s gonna be a new phase of go-to-market and selling in general. 

Yeah, for sure.

So, just double-clicking, so who are your buyers? Who are the buyers of Velas, and how do they use them? How do they use it? 

Yeah, so we, as a business, really focus on our core competency, which is enterprise SaaS. So our core market is gonna be large enterprise sales teams. Usually, if we look at our current customer base, somewhere between 100 sellers to our largest company has closer to 3,000.

And we really focus on those larger teams because there’s so much value in the small tweaks that we can do with that team, because it’s exponential. With that being said, we do have sales teams of five people, and those are in our ICP. We don’t go outbound to those businesses, but they have come to us, and they’re still a great fit.

But our ICP is a large B2B enterprise sales, and they’re using us in a few different facets. So they’re using us for this use case building exercise, where they can identify either from call recordings or through templates that their marketing team and product team put together. The use cases that the customers’s coming to them for.

They can estimate the number of credits or other product packaging that’s going to support that use case. And then we have a pricing calculator that helps them put together slide deck presentations or other types of pricing presentations, and then integrate this fully into their CPQ. If you kind of think about it, you could have a gong or a flurry-type call recorder, and we’ll take that transcript all the way through to your CPQ and your close one deal.

Understood. 

So that’s a good segue into the next segment, which is the go-to-market success story and a go-to-market pivot story. So we’d love to get your insight and learnings from both the go-to-market success story and a go-to-market pivot story, ideally from Willis, if you can share that.

Yeah, I think I have two that come to mind, or one for each of those questions. I think the success story comes back to the first thing I said on how you define go-to-market, which is how you show up for your customer. When we first started the business, we were focused on the pricing aspect because we felt the pain with Salesforce CPQ and Zora CPQ in our past lives. We knew that as a seller, I wanted to present multiple options, present multiple ways for my customer to buy my product, and not just be an order form generator over and over.

And what we learned early on is that the way that we showed up for our customers was actually the best go-to-market channel for us. Pretty much every business, every large enterprise that has come on board with us has been referred directly through a referral. And so when we show up and we say, hey, why are you using our product? What is it that makes our product something you log into every single day? We started to identify those use cases, and we started to identify how our product shows up for our customers.

And then we continued to kind of poke at that. And I think one of the benefits of a founder-led sales org or coming from being in sales is you’re not afraid to ask a lot of questions. And you’re not afraid to ask more confrontational questions, not in an angry way, but like, tell me more about that.

Why is it that, like, I always loved the Sandler selling method? I always loved to disqualify things. I didn’t want to waste my time on things that weren’t real.

And so part of my product questions and product discovery with our customers is like, what if I took that away? If I just deleted that out of the app, would you be mad? And that led to really identifying use cases. And then to your second question, like the GTM pivot, if you will, I wouldn’t say it was so much of a pivot, but it was really identifying that, like, hey, everyone’s really enjoying the pricing workflow that we help large enterprise teams with. Now, everybody really wants ROI.

And so I think the holy grail of a sales rep is here’s pricing, but here’s exactly the ROI that is believable to their customer. And so we went down this path of identifying, well, ROI in general, a large-scale ROI exercise is two, 300 questions. And it has to do with every little, you know, tiny bit of my product.

If you use all these products, the ROI is 20 X. And I used to go through those exercises with my customers in past lives. And at the end of it, it would have this incredible graph that would just show paying for itself 200 times over. Their eyes would glaze over, and they wouldn’t really care about that ROI at the end of the day.

And so our pivot moment was, wow, ROI is not as important as we thought about as we look at a grand scale of a sales motion, but it is incredibly important when we think about the specific use case. So it all really came together. Use case-based selling, in my opinion, is how enterprise sales teams will sell moving forward because ROI matters, value engineering matters, and pricing matters as it relates to the specific use case and not a whole grandiose kind of product offering.

Yeah, for sure. I mean, that definitely resonates, use case-based selling. So I wonder if WCAG can make it even more concrete for the listeners.

I mean, as a concept, I get it, use case-based selling, and even the concept of jobs to be done, and how do you simplify the whole thing? I get that. But if you can make it even more real with an example, that’d be awesome, Simon.

Yeah, I’m more than happy to give the Veles examples. I think we were able to quickly identify use cases that people really cared about when they came to us, which, for a large enterprise sales team, automating the deal desk is super important. And it’s not to replace deal desk teams.

Deal desk teams are incredibly valuable, so we’re not replacing a single deal desk person. But if we could really dive into all the steps that make deal desk a friction point in sales, if you can identify all of the stocks compliance that needs to happen to ensure deal desk is working effectively, one of the biggest use cases is minimizing the number of deals that need to go to deal desk that shouldn’t actually be in deal desk. 

Got it, yeah.

So deal desk is a great strategic lever. They are gonna help your sales teams build the correct deals for your enterprise partners, but your SMB and your mid-market deals probably shouldn’t be in the deal desk as often as they are. And so one of the use cases that you come to Veles for is that we really want to eliminate the wasted time our deal desk team spends on SMB and mid-market deals, because really, they should be going through their manager, getting approval based on a very clear set of boundaries.

That’s a great use case, but also our sales teams are spending an insane amount of time building out manual presentations and slide decks. They’re spending a lot of time in Salesforce CPQ before the deal is real, before we’re actually getting an order form generated. Yeah.

And so all of these kinds of disparate, but difficult steps are wasting, on average, about 30 to 50 minutes per deal for a sales rep. And most sales reps are doing 40 deals a month. So it’s a significant amount of time that a specific use case could solve for.

Got it. And you can clearly show the ROI just based on the time numbers that you’ve shared, right? If you imagine both for the deal desk and for the seller, if you can cut down for the deal desk, it’s like the number of deals showing up at the desk; you cut that down and times the number of deals and the hours, you get the ROI. And same thing for the sales rep in making sure that they prioritize and work on the right things versus jumping two, three steps ahead for tasks that are not relevant yet.

Absolutely. And I think of the use case piece as well, if you know why your customers are coming to you, then you also know what you should be focused on from a sales rep’s perspective. 

Yeah.

If there’s a use case that just doesn’t have a high success rate, then you can start to filter out those deals. You can take that Sandler selling method that I’ve been such a fan of in my career, to really start to spend time where you need to spend time to be successful. 

Yeah.

So, can you repeat that sales methodology that you just mentioned? 

Sandler selling. 

Sandler selling. Okay, got it.

I was not aware. I’ll definitely check that out for sure. Yeah, it’s great.

They have some great books, and they have great courses you can take. I haven’t taken any of the courses, just as an FYI, but I do love their books. Yeah.

So, going back to something that you mentioned earlier, getting your customers for Veles, it’s mostly through reference, which is how it should be. That’s a validation of how sticky the product is. I mean, an early indicator of product market fit.

But obviously, for you to get a reference, you need your first set of one, two, three, four, five customers. So, how did you land those first five customers? 

Yeah, we were really lucky in the early days to actually land a large enterprise. And I don’t think it’s a shock if both my co-founder and I worked at Procore, so they would be one of our first customers.

But I think that there’s a significant amount of pain around the Salesforce CPQ and Google Spreadsheet tech stack that lives in most enterprise sales teams. I think for a lot of your listeners, they’re probably gonna go, well, that’s exactly our tech stack. And that’s not shocking because Salesforce CPQ is a super important part of your business.

And any CPQ, if it’s new.io, if it’s deal hub, if it’s Zora, all these CPQ tools are incredibly important. Do their job, which is revenue recognition, subscription management. That’s a huge part of running a large SaaS business.

But what it leaves in the wake is a lot of really frustrated salespeople because they don’t need to spend that time generating an order form just to get initial pricing out. And so we’ve actually found that through Outbound and also just through that kind of network, once somebody experiences Veles and they use the pricing calculator and they use the case builder, it’s almost like I can’t go back. It’s like, I can’t unsee this.

And so we find that when we work with really large organizations with thousands of sales reps, there’s always gonna be churn within the business. And as those people leave and they go to other organizations and they realize they’re using Salesforce CPQ and Google Sheets, it’s pretty inevitable within the first few months, we get like a LinkedIn message or something saying like, hey, we should really solve this over here. And so that’s just been really fantastic for us is landing those first few big customers and then working through those sales to really make their experience better.

Yeah. 

So that’s our early go-to-market. I mean, coming back to the whole go-to-market concept and what this podcast is about, go-to-market is always evolving.

So your early go-to-market, yeah, you go to your quote, quote, friends and family, and get your first set of customers. After that, it’s a referral. And so, how do you see well as go-to-market unfolding over the next six, 12, 18 months? 

You know, I will preface this answer by saying, I don’t know, because this market is changing so fast.

Yeah. 

I’m really bullish on some of the go-to-market tools like Clay. I think that we’re able to do so much more with smaller teams than we used to in 2015, 2016, right? The answer then was to throw more bodies at it.

And at the time, that was the right answer. 

Yeah. 

I’m not so sure that’s the answer now.

And so our organization, you know, we really love to be lean. We like to be the smallest team we can and do the most with our time. But we also are solving a super hard, like we’re in the hardest parts of the business, pricing and packaging, logic, deal desk rules, compliance, like everything is really important to get right the first time.

So we don’t take a growth at all costs approach to this, but we do try and grow as fast as we possibly can. And I think we’re gonna continue to use as many tools and AI to do that as we can, while making sure our approach is very human. So it’s not a great answer. It’s a more pie-in-the-sky answer, but I think you gotta keep approaching it that way because the market’s changing too fast. 

Yeah, I mean, that’s a good validation, right? I mean, that’s, I would, I’m actually surprised when people say, hey, this is the exact go-to-market motion that we’ll play out in the next 12 months, especially in these times. I mean, with the way that AI is changing go-to-market tasks across the board, there are a lot of unknowns.

You cannot be fixed anymore. And so I, yeah, it’s not a pie in the sky answer by any means. And especially given your early stage and you’re still growing and figuring out your way, your point, you’re totally spot on in terms of, you will have a hypothesis that you want to test in the next, what? Two weeks to 10 weeks or 12 weeks.

And then you just iterate. 

Absolutely. I think one of the best things you can be as a founder is okay being wrong.

Yeah. I’ve learned that time and time again because I’ve time and time again been wrong. And I think that, like, I think being wrong is good because you’re proving something, you’re testing something, and you’re iterating and changing.

Being wrong and not changing is the worst thing. Ah, sure. And so go-to-market is one of those.

It’s just awesome to see what organizations are doing and to jump on the things that are working and to be okay with the things that aren’t. 

Fantastic.

So coming to the final portion of this podcast, I know we can go on and on on so many topics, maybe a follow on for podcast later, but yeah, coming to the last couple of questions for you, Simon, like who do you think, or what do you think are the key resources of the people or mentors or like podcasts, events, books, what really shaped you to what you are today? 

Wow, that is a, I could do a whole podcast on that, I think. But, you know, I was really lucky in the early stages of my career to have great mentors.

I had people really pushing me to understand that, you know, how you show up every day is equally as important as the results that you put out. And so I think that really helped me early on. I thought a slew of sales books and a slew of product books, and crossing the chasm, and all these fantastic books.

So, people who have done it before were super helpful in understanding how to run a business. And then I would just say like, you know, I was a stretch hire even as a BDR and as a seller and as a head of sales, like I think that being able to put yourself in risky situations and being honest about the fact that you don’t know, but you’re excited to find out is maybe the best thing you can do in your career. So I don’t know if that’s directly the answer, but if that’s something I could tell myself, I would be even more of that as a 21- 22-year-old.

Yeah, you actually segwayed into the final question, which is exactly- 

Oh no, sorry. 

That’s fine, I’ll still give you a chance to expand and double-take on things that you didn’t mention. So, going back to that, right? So, if you were to turn back the clock, what advice would you give to your younger self? 

I think the advice I give to my younger self is to be even more inquisitive about the problems that other people feel.

As an early seller, my core focus was closing deals. I mean, I was just, I felt it was human chess. I thought it was a fun interaction between people.

And I still feel that today. But if you ever want to start a business, if you ever want to be a founder specifically in tech, because it’s just so competitive, you have to know the problems that you’re solving better than anyone else. And so as an early-stage tech salesperson, if I double-tapped, if I were to go back in time, I would just ask everyone in the org what problems they feel.

If you can learn your customer’s problem, then you’re going to be successful because nothing will prepare you to be a founder. There’s you can read enough books to know what to do once you start your own company, but you can also learn how to solve somebody’s problem. Fantastic. 

That’s a great note to end the podcast. And that’s a recurring theme, by the way, as Simon Waddy has mentioned. Across the board, people always emphasize, if you spend time in knowing about the problems that you’re solving for your customers, that is the number one way to win as a business, right? So, thank you for reiterating and emphasizing that.

Dive into the latest episode of the B2B Go to Market Leaders podcast, where Rachel Stanley, Vice President of Customer Experience at Banzai, shared her career journey and deep insights into customer experience and success within the SaaS industry.

From starting as an onboarding specialist to rising to a VP role, Rachel’s story highlights her initiative-driven approach and dedication to understanding customer needs. She emphasized the critical role of the first 90 days in customer engagement, the importance of aligning customer marketing with experience, and the need to balance empathy with revenue responsibilities. Rachel’s insights provide a comprehensive guide for anyone looking to excel in customer success by integrating empathy with strategic business goals.

Rachel discussed the significance of a well-defined Go-to-Market (GTM) strategy, the ownership of expansion revenue by customer success managers, and the evolving nature of customer success roles. She also highlighted the importance of structured onboarding, aligning marketing efforts with revenue outcomes, and fostering accountability within teams. At the core of her approach is a commitment to helping customers achieve their goals, underscoring that true customer success is about balancing business objectives with genuine care for customer needs.

Listen to the podcast here:

The First 90 Days: Guaranteeing Revenue Growth Through Customer Success with Rachel Stanley

Signature Question: How do you view and define go to market?

I view it, I mean, this is just how a company engages with customers to promote and sell a product or service.

Very cool.

Simple. One line. And that’s it. As simple as that.

Yeah. I mean obviously so much goes into it.

But.

It’s like the the plan to get you like, how are you going to engage with customers and prospects? obviously, my focus is customers. So how to upsell and cross-sell? Yeah.

Yeah. So sounds like most of your responsibility is more like post-sales. More on the customer success side of the house.

Exactly? Yeah. So everything posts, sale support, onboarding, customer success, customer marketing. Yeah. so we chose customer. We decided customer marketing should fall under me because we have the same objectives. So it’s worked out really well for us instead of having it under marketing.

Yeah. Very cool. And I think if I’m not mistaken, you are the first or definitely the early or like the initial set of people who are.

Coming in from a customer success or a customer experience perspective on this podcast.

Oh cool. Okay.

Because mostly we have had like founders, like Y Combinator founders.

Okay.

Or we had like chief product officers, chief marketing officers, revenue officers. Not a whole lot. I mean, so I want to grow that size. So you’re the first or the initial set.

Right? Okay. Interesting. Yeah. yeah. I’d love to dive in. I have some perspective. I did take on, like a VP of revenue role for a period of time when the company needed it.

Yeah. And then switch back to just customer experience because it’s definitely my sweet spot.

So very cool. So that’s a good segway into why don’t you walk us through your career journey and what led you to what you’re doing today.

Yeah. So back in my first customer-facing role in SAS was in 2012, started as an onboarding specialist, then was promoted to an implementation consultant, and then ended up leading the Consultant team and then switched over to Customer Success. And because it was still kind of new, you know, back then, like the actual customer success, like at least the company I was at was it felt kind of slower to get there than some others. But, I was really curious to expand into customer success. So that’s when I came to Bonzai. so I came to Banzai and Customer Success was the only customer-facing role at Bonzai at the time. And it was a startup and, very highly touched customer success. and I ended up adding a lot of processes and, you know, onboarding and things that I’d done in the past.

And so the CEO promoted me to director of customer adoption, and where I really focused on the first 90 days and then took Then I, inherited our support. Like, creating a support team. Like a true reactive support team. Yeah. Then, I got promoted to VP and added onboarding or customer marketing after that. And customer success.

Very cool.

So now it’s support onboarding success and customer marketing.

Very cool. So you pretty much are obviously with your team, you’re in charge and accountable for all experiences of the customer post-sale. Yes, exactly. Very cool. Yeah. So going back to your early days, you started off as an onboarding specialist, and then somehow clearly you did a pretty good job and you got promoted into like a consultant and then the team lead for training and implementation. I mean, it’s onboarding and then training and implementation. So talk to us about that journey. Like first of all, how what made you Attracted or what got you into onboarding in the first place, and then training and implementation?

Yeah. It’s fun to think back. So I was, I was at you know SaaS company and I was actually the office manager and executive assistant. And I had been doing that for a while. And, the role of onboarding specialists opened up. And I just thought, you know, I’ve been treating like employees as customers, like I’ve always loved like hospitality and, you know, like have always, you know, like your job my job is in high school and college or like coffee shops and, you know, sandwich shops and things like that. Yeah. and so I was like, this feels like a good time to, like, kind of take a pivot. And so I applied and, and got the role. And then when I, I started, it was like a really I kind of realized that All right. Did realize that really what I was doing could be automated. Pretty like manual is like provisioning accounts and you know, a lot of manual stuff that there was some like getting on with customers but not as much.

And I wanted to do more. And so I coordinated with our front-end engineers and the team and actually did automate the onboarding process I was doing. And so then that opened the door for me to be promoted to the implementation consultant role.

Got it. And then you also took on training in meditation.

Yeah, exactly. So training was we looked at it then as like it was a little more like point and click, you know like this is how you do something. And the consultants were more like, we did a lot of like one and two days on sites, you know, really digging in, understanding the business. How? Yeah.

Got it.

So I do have a question about the training and onboarding, not training, but more on the onboarding side of things and the softer products that are coming out in the market today. Products like Story Lane, I don’t know if you’ve heard of Story Lane and similar, which is very interactive. I mean, now people I’m not users there can actually go and you can create an automated interactive onboarding experience.

Cool. Okay. Yeah, I am very much for that. I mean, I think people, you know, not to replace human experience, but some people. But I think you have to provide all of the options for people because everybody learns differently. And so what we’ve done at Bonzai is we have an in-app product tour through. We use the intercom for that. Yeah. and then we also have you heard of Nevada?

Nevada? 

Yeah. So we use that as an onboarding tool as well where it’s like you can actually click. It’s kind of like a product tour. But it’s used also like on websites as a demo-type tool that you can see. So we use both of those. But then we also have onboarding specialists that it’s an option for people to use. Got it. And training webinars and stuff.

Yeah I know we got a little sidetracked with the automation tool, but coming back to your journey, so you then took over or joined, Bonzai as enterprise customer success manager?

So what was that like, or what made you pick that role?

Yeah, it was pure interest in customer success. I showed interest at my previous company, and they wanted me to move to the headquarters to do it, but I didn’t want to move to South Carolina. and so I was like, okay, I’m going to find I was like, really interested to kind of find a startup that I could make an impact at and just like, feel that community. And, ended at bonsai and it was a so I went from leading a team to being an individual contributor, which. Yeah, was now, I’m glad I did it because I had so many growth opportunities thankfully, since then, but it was kind of a risk. And I found myself kind of like itching to lead the team, you know, lead the team when I started. But instead I just, you know, pitched in and helped with like more operational and process improvements and, you know, things like creating slide decks that the SMBs weren’t doing at the time.

And that got the CEO’s attention.

Yeah. I mean, clearly, it’s I mean, just based on your initial couple of goals, something that’s coming out as a pattern for me is for you to take initiative. I mean, you are very self-driven. You take initiative. You actually do things beyond the scope of your current role.

Yeah, it’s very evident.

Yeah. Thank you.

Yeah.

Yeah. I think that’s an, you know, obviously important. And now I look for that when I interview people.

Yeah. Very cool.

And then after that, you became the director of customer adoption. So it’s like customer success and product adoption.

No, it was it was kind of more in the onboarding sphere. But, the first 90 days. So I had customer adoption managers. It was kind of a mix between onboarding and CSS. Like how we ended up doing it was like the adoption manager owned the customer for the first 90 days, and then they graduated to the CSM.

So like I used to say, I wanted to hand over the customer, like wrapped in a nice present, you know, like they’re totally ready to go. All you have to do is like, maintain the relationship and they’ll renew, you know. So.

Right.

And so one question that keeps coming up, I see in the GTM world and discussions all over is when are what are the criteria that you would suggest to invest in the first 90 days of onboarding? Like is it the ACV or is it the product complexity? Is it, the type of accounts? So what are the criteria that you recommend?

Yeah, I would say definitely ACV is like our product. Now we have multiple products. So I manage the first 90 days differently for, you know, and the different tiers of each product. But hi HCV and the complexity of the product like at that time, the product that only product we had a high ACV. And it, it took kind of a lot of coaching through it.

Yeah. It wasn’t as self-serve as some products are. Yeah.

Yeah. And we’re talking about like five-figure six-figure on an annual basis.

Yeah. Yeah. But yeah, like I think, you know, some were well into the six figures but all were at least. Yeah. Like, the low end was 30,000. Yeah.

Got it. Understood.

And then after that, senior director, customer adoption and support, and then VP of customer experience, and then VP of revenue and customer experience and customer marketing as well, falling under your charter.

Yeah.

Yeah Yeah. so so curious. I mean, what is the discussion like or a thought process or how did you pitch? I mean, typically I’ve seen customer marketing mostly under marketing or maybe within product marketing. but what is the thought process like?

Why it should be I know.

Right. So the CEO, VP of marketing, and I got on a meeting to discuss it because we hadn’t had a customer marketer, at all before. And ultimately the decision was based on like the objectives, like, what are the objectives of the customer marketer marketing going to be? And we decided at least to start for the first customer marketer, it needed to be revenue attribution, tied.

And for our use case, it was tied to expansion and re-activation. And that’s, you know, that’s basically that’s one of my objectives like my ultimate objective is an RR, but like how you get to a higher end RR is more than retention. It’s expansion and reactivation and, you know, cross-sell. So yeah.

And another line of discussion on this topic that I see, play out in different GTM scenarios is who owns the expansion number.

That sales or customer success?

I just had this conversation. I, we had a field event in Toronto this week that I went to, and the people that I was sitting next to, a director of Customer Success and across was her head of revenue. and they do it where the revenue like he has account managers that own expansion and revenue and renewals and her customer success managers just are focused on like success and and helping where for us CSM Cosmos handle all. I mean, they’re measured on revenue.

So renew.

Renewals and expansion.

Yeah, exactly.

And again, it kind of goes back to your other question of like even investing in the first 90 days, like talking to them in their product, it does make sense because it was like a very it sounded like a very hands-on, like a low number of customers, like the customer success manager really needed to be there to, like, help them be successful and then but what I, I think made sense that I like that they did is the cosmos were measured on SQL. So they had objectives to at least like refer their customers to the account managers, you know, for renewals, but also expansions for us and our use case. I still think I like having TSM. both. It doesn’t really solve the problem. I know what I’ve heard is that it creates kind of a tension, but we have I don’t feel like we’ve run into that.

Got it understood. I think it also boils down to the capabilities of the customer success leader. and because clearly it’s not like you owned or were part of a revenue number or target early on, especially during onboarding and training.

Right. But something I mean, something happened. What was that like? And how did you start positioning yourself in that revenue ownership direction?

Right.

You know, it’s funny as like, even at Barnes, I, I switched who I reported to, like I was under the go-to-market leader at the time when I was, owning adoption and support. And then they switched me to operations because they were like, oh, like she’s not owning a revenue number. Yeah. And. But I was a CSM and I was very I’m very competitive and I liked hitting goals. So I think that’s, you know, like conducive to having revenue numbers. And so but then I’m also like super empathetic and you know, so it was like yeah. Where like onboarding and stuff, I could tune in to how people needed to learn. And. Yeah. so I think that’s what got me to where I am today. But I think the transition was just realizing, like how energized I got by, like, hitting numbers and like the adrenaline rush of it all.

Yep. Yeah.

Yeah I mean the thing is always a double-edged sword. I mean the best thing is it’s you can measure it very clearly. I mean if especially if you’re a very focused, persistent and goal-oriented person, a leader, you know, what you need to match towards. Yeah. But at the same time, if you’re not hitting the numbers, your role is at stake.

Yeah, I know, which is it? Yeah. Like I feel the pressure, you know, like we all do. Anyone that has a revenue number. for sure. But it’s still, like, kind of gets me up in the morning, I don’t know.

I like it. Not for sure.

I mean, it’s easy, right? I mean, that’s how I look at what I do as well. because I run my own consulting practice, which means. Yes. In addition to delivering the services, I also need to hit forecast and then predict and actually go towards those numbers all the way through.

Right. And that’s what gets me going. Of course, the the toggling and context-switching take a toll for sure. but again, that’s, you know, at the end of the day, if you’re doing well or not, it’s black and white.

Yeah, I agree. Yeah. Actually the the director of Customer success, I talked to Her opinion was that it’s hard to find people that are good at like success, like helping the customers be successful and rather than you, which might, you know, it might be true, but I do think we’re out there.

Yeah. Yeah.

Exactly. I mean, because typically customer success, especially if your mindset and thinking is around and strength is around empathy. You connect with that customer, the account, the people in the different teams, and so on. And you’re always on serve them and help them be successful. But at the same time, you need to play almost like doctor Jekyll and Mr. Hyde. It’s like a switch. You know what? At the same time, I have my numbers ahead.

Yeah. I need to close you at any cost. That is all the running in your head.

I know it’s for sure. It’s a balancing act. And that’s the. It’s like a win-win. When you can figure out that this is actually what the customer needs, right? You know, like upgrading is actually what they need or like cross-selling, you know, so that’s what we’re trying to focus on.

Yeah.

And then the last question on this topic, which is at what like for which role did you actually take on the revenue and numbers responsibility? Was it in customer adoption or customer success?

the customer VP of customer experience was really I took on everything.

Yeah. Yeah.

That was, back in 2021, 22.

Roughly. Yeah. Very cool.

Yeah, I know we can go on and on just on this topic. Let’s switch gears over here. let’s, Yeah, you’ve had interesting, right? You’ve been fairly stable compared to folks in Silicon Valley who are always job hopping.

But at the same time, you got, you’re consistently in the post-sale.

Well.

For sure. I mean, customer onboarding, training support, customer success, and then customer marketing. but now on a lighter note, what does your family think? how do they describe what you do for a living?

I love that question. My daughter is 11 now, but when she was younger and cuter, a babysitter told me that it was like a new babysitter. And she said I asked my daughter’s name Haven. I asked Haven what you do, and she said, you help people. And I was like, oh, that’s so cute. She’s like, how do you help people? Like, are you a nurse or something? Like no, no like I explained it to her, but I love that because like really that is what I do like. Like I help my team, you know, to then help our customers, which then helps them help their customers. You know, like it’s like the cyclical thing.

And I love, like connecting to the heart of that. Yeah. but I think now she would probably I don’t know what she would say, ramble on about something, but I like I like thinking of that when it that my family knows I help people and like, I lead people.

Yeah, it’s completely true.

Right at the essence, at the core customer experience and customer success is all about helping. And you obviously need to help your employees. But at the end of the day, are you helping your customers? Right?

Yeah. That’s right. Exactly. Very cool.

And even on the lighter side, and on a personal note, what your family and your daughter think of is cute and sweet, for sure. Yeah. coming back to Bonzai, like, how do you describe your customers and the personas and how are you helping in the overall goal market?

Yeah, so our different products have different, you know, ISPs, but really it’s the B2B tech. Our, webinar platform also is a healthcare and financial service is a big part. But mid-market and enterprise customers as well are our biggest focus and like percentage. But for the webinar platform, we also have like you know, solopreneurs and SMB very cool.

And then who are the buyers and the users of the webinar platform?

Primarily marketers. So we definitely, you know, advertise ourselves as a martech company. However, really, customer success and sales are also personas that we sell to.

So really the whole go-to-market function.

Vertical and some sorry, something that I’ve seen, especially when I’m working overall if I’m part of the marketing team and I’m trying to build the overall customer journey and understand the go to market clearly, I see a lot of value in partnering with Post-sales. So customer success, customer support. So from that viewpoint, I mean, how do you and your team, how do you contribute and play a role in building and improving the overall customer journey and the go-to-market for Banzai?

Yeah. so the customer journey, like obviously we’ve mapped out the post-sale customer journey. But one area of overlap that’s been interesting is the for our webinar platform, the trial experience, we have a 14-day free trial. Yeah. there’s onboarding for trial users, but the trial isn’t, you know, under my umbrella. And so we’ve worked together closely on the onboarding experience for trial versus becoming a paid customer. I think one thing for our other products and we have I’m especially involved right now, we’re really looking into a lot of acquisitions right now, and I’m brought in a lot for like, is this cost sellable? like, I’m like, one of the like it has, you know, it’s like I’m interviewing different acquisitions to make sure that we can cross-sell it.

Right? And then just like, bringing the voice of the customer, like, what are the things not only that customers want, but like, that are the most valuable. Like, why did they buy it? Because we get to learn why they bought right after they, you know, buy especially in like a self-serve motion that they didn’t go through in a that can, can, you know, tell that which helps us know, you know, helps the pre-sales know what to promote the most and, and all of that.

Yeah. And then something else that has seen really, I mean, play a big role, especially in messaging and, go-to-market campaigns is understanding the value prop. Yeah, I think that’s what you’re referring to. Why did someone invest in your platform versus the alternatives, right?

Yes, exactly. That’s a better way to do it.

Very cool. So, switching gears, you had a vast experience in post-sales. Clearly you’ve seen success and failure. And so if you can share a good market success story and a failure story, I’ll let you pick which one you want to go with first.

Okay. I’ll do success. so we actually want to know award recently for the story that I submitted it through CMS Wire Impact award for customer journey Innovation. so and this is for the webinar platform I’ve been referencing, but we have a monthly plan and an annual plan. the annual plan saves you 30%, which is actually, you know, normally it’s like 20 to 30%. Yep. but our, so our percentage of revenue and our percentage of customers were still so high monthly customers, which is just, you know, makes you nervous because they can turn at any point. And, you know, my ultimate thing with PNR is like, okay, how can we increase PNR? So we really focused on ways to encourage throughout the customer journey, like when was the right time to re-promote, you know, an annual. So when someone first buys they see the two different prices and my assumption psychologically is like, well, I’m going to buy monthly to make sure I like it. And then two months in they’re happy or three months and they’re happy, but they forget that they can save 30%.

Yeah. And what I liked about this initiative is that it was like a win-win situation because it saved the customer money, but also like gave us more stability in more annual contracts and forecasting. and so 2023 so last year, we focused on it the whole year. through customer marketing initiatives. And we increased our MRR ratio by 8%. Nice. We, you know, I’m happy with like obviously we want to keep increasing it more and more. But it went from only 36% of our MRR from annual to 44%. the last I checked, we were at like 51% already for this year. Yeah. So, we’re we’re continuing to tweak messaging and find the right times. But I think for us at least, it’s like the 2 to 3-month range is when people are ready.

So very interesting case study and success story for sure. A lot of questions running in my mind, which is how did you arrive at the 2 to 3-month mark?

So one that was like, assumption.

Honestly, like in my mind it was like, okay, like if I’m testing out a or like past experience, right? Like if I’m testing out a product after 2 or 3 months, I know if I want to keep using it or not. Yeah. And so that’s just what we started with. And then and we were just seeing like such a, a good response. Like initially we just sent out a blast email to everybody that was like, hey, did you know you can save 30%? We got like a lot of people are obviously like, oh, no, I didn’t know that. Because really, 30% is like getting four months free, you know?

Exactly.

and then we had to figure out the customer journey, and, we tried two months and then three months, and we landed on three months. And even that is helpful. Like, now we have onboarding, you know, focusing on the first 90 days. And it’s kind of a goal to get them to an annual contract by the end of the 90 days.

Got it. Understood. And then you also mentioned the different segments and the personas, right? You mentioned about marketing. I mean, Post-sales support customer success. Are you seeing any demarcation? And you also mentioned about the different industries. So seeing any demarcation and segmentation behavior playing out like, yes, renewal and expand, but then maybe it’s some person or geography or industry.

Yeah. I mean, for us, mid-market and above is like by far, our best. Yeah. In our AR which makes sense. You know, like we, we use clear bit to enrich our data and the unknown, you know, like the customers that clear bit can’t even recognize what their revenue is, but their churn rate is three times 3 to 4 times higher than the rest. Like even just even including us and be.

Yeah.

And so it’s mid-market and post like three months. Around the three-month mark. Yeah very cool. And so is it even across the different personas and functions.

That’s great I feel like I don’t have and I definitely don’t have good reporting for like this user is a marketer and this user, you know, to get to be able to. But just like talking to customers. Yeah. normally customers’ success in sales is like additional use cases that are added on. The marketer is like the owner.

Got it. And so and normally once they add on the different use cases it’s stickier. Yeah. So they’re not churning.

I mean this is great. I mean the success story and the case study and the data that you are coming up with is like gold for marketing and sales.

Yeah.

Exactly.

Yeah! Very cool.

Go ahead.

I was going to say, I think one of my failure stories, though, is like, I’m not happy with how well we’ve expanded our use cases to customer success in sales. Yeah. because I don’t know, it’s like we did this whole push because one of the reasons we did a push was because our pricing for the webinar platform is host-based, like, and really and a lot of people share logins, you know, like it’s tricky.

And so it was like, well I doubt like different teams are going to share logins. Right. So there might be like a marketing at login and a customer success and a sales ad. And so we know we built together with you know, marketing. And so like on our website we have different uses.

Pages now. And, you know, we definitely saw some success, but I’m just not happy with how well the success like our multi-host customer percentage is just too low. and so I’m still kind of noodling on how to better expand into the use cases. And, I think part of it is just continuing to promote the value of webinars for each of those. And I think webinars are a lot of work. Yeah. And so like how can we help make them easier?

Sure. Yeah.

Yeah. I mean, one of the things that come to my mind is essentially around how webinars as a channel are being effective for lead gen and even expansion for other customers.

And I’m sure you and your marketing and go-to-market team are always thinking about showing success stories.

Yes exactly. And like how to measure the ROI of them.

Exactly. Yeah. Switching gears, but on a related topic again, which is how close is your interaction with the product marketing function?

So we don’t have an actual product marketer, which is. So I actually have a page. So my customer marketer is like also our product marketer basically. and then our product manager fills in some gaps like research type. So my customer marketer does all, you know, the feature releases and stuff like that. And so I’m, I’m really hopeful we’ll get a product marketer this year. But we, they do meet like our product managers and demand and like our director of demand gen and customer marketer meet I think bi-weekly. I’m not I won’t join that meeting. But they’re they work very closely together Yeah.

I mean, typically what I’ve seen play out in very established and mature go-to-market organizations, is product marketing has maybe six or even seven, eight functions starting with positioning and messaging.

Yeah, that’s one of the key topics. And then after that, there is also the user and customer research program that has to be in place on an ongoing basis. And then you have the product content. You have sales enablement, especially if it’s sales lead, go to market, and then you have a new market, new product launch, product expansion, which will fall under your bucket, and then product content overall.

Yeah, that sounds very dreamy. Like we’re we’re still a little scrappy where we all like, you know, like help like okay, the CSM are doing the user research like during their calls and you know, things like that.

Yeah, yeah. Fair enough. I’ll make a note to myself and happy to provide guidance on these topics. Product marketing and growth is my area of expertise, and that’s where I help my clients.

Awesome. Yeah. Very cool.

Yeah. And then, what are the typical wanted to go to market skills that people look out for and think of you like, really? Oh, this must be Rachel’s strength.

Let me go get her advice or input.

I have, like, just such a deep understanding of our customer base and our business objectives. And so I mean, even this week in the exact meeting, we were talking about how to like, expand use cases for one of our products. And the CEO was just like, Rachel, you, you know, you understand the as I should write like you understand our customers the most. You’ve worked with them the most. Like I make sure to do customer visits. I, you know, do calls, I stay, really. I keep a close pulse. And so, but then also just having a really deep understanding of, like, our business objectives and goals and priorities and things like that. So the teams below me know, you know, they understand our customers, but they might not know what the priority should be. so, you know, it’s like I provide a bigger picture of, you know, the whole thing.

So I, I also just love throwing out ideas like, I’ve actually really loved adding customer marketing. Like when I hired our customer marketer, I was like, listen, I’ve never led customer marketing. I’ve never done customer marketing like the other job function. Well, I’ve never done support. But, you know, like I was like, I really need you to own this, but I’ve just like, loved it. Like, I like we get on and brainstorm and, and so I it’s been kind of fun like from that go to market perspective because it’s you know I think marketing feels a little closer to go to market than what I had done in the past.

Yeah. I mean something that I’m seeing is I mean, somehow you got, the knack of picking up new functions and doing well and not just as an individual contributor, but even thinking about the strategic part and the KPIs on the business drivers.

So what is your secret sauce? Okay. Replicate that. Thank you.

That’s so sweet. What is my secret sauce? I think I love clarity. Like. Well, one as you mentioned earlier is, like, you just have to, like, take initiative and, you know, be self-driven and like, I think the like competitive nature. Not like I’m trying to beat other people, but just like, like to hit goals. but I also love, like, working through, like the muck of like, okay, but what’s like the essential thing? What are we actually trying to do? Like, what’s what’s going to get us there the quickest? Right. I think really thinking through like, this year, I’ve had this whole focus on essentialism because I read a book called essentialism and, I think that really like, describes what I like, geek out over. It’s like it’s kind of like a mix of minimalism and like, I love minimalism in our house, you know, things like that. So yeah, if that answers your question, but.

Definitely, I mean, the the way I think about it in similar scenarios is, for me, same as you, Rachel.

I love to build and bring structure in an ambiguous and chaotic environment. And the way I arrive at it is again, to look at what are the business objectives, what the business objectives are, and then what do I need to do to build clarity around it? Do I have the right leading indicators? Because KPIs are typically trailing indicators because I need to know if I’m doing the right things and making progress towards those business objectives, and then constantly learning, keeping my eyes and ears open. And this is podcast, is one of the things and resources that I lean on and mentors and other folks.

Putting all these things together in place.

Yeah, yeah I love like I would definitely tag on the learning part to like I and Bonzai is like one of our company values is learning. And so there’s a high emphasis on learning and and hiring people that want to learn, or continue to learn. And so I think that’s you have to like, I mean in some ways I feel like I’m self-taught, you know, like, just like going out.

And thankfully, we live in a time that it’s, like, very easy to, to learn, you know, podcasts and just googling things and, you know.

Absolutely. And then if you were to look back in your career, like, who were the people who really shaped like mentors, sponsors or people who just guided you and acted as a mirror?

I would say my the first manager at my last company that, gave me my first leadership position, like I he was my manager for six and a half years. So I really learned a lot from him. And like, I’m thankful that he gave me the, you know, my first opportunity. And then the same with the CEO of bonsai. Like, he’s promoted me a lot of times here, and I just feel like his faith in me is, Has what like has propelled me to keep learning and growing like that. He believes I can do it. And and then the the third person is actually kind of newer and she would be shocked probably to hear this, but we’re, Gartner clients.

There is an analyst there. That is I am like a super fan of she’s an older CSE leader that I like. I don’t know, like we’re just on the same wavelength. It’s like, the way she explains things and, like, I just feel like I want to be her when I grow up. So she’s really helped, especially adding all of these job functions the last two years, like my inquiries with her and the articles she’s written. And like, I’ve gone to Gartner conferences and I go to all of her sessions like she’s really helped me a lot.

Very cool.

Again, it goes back to just reaching out and seeking people who are sharing the beliefs and pursuits and then learning from them, right? I mean, you can go and seek out and ask them to be a mentor. Officially or unofficially?

Exactly. And like with her, I have, like, an eye at. I ended up just asking for a monthly inquiry. Yeah. which, thankfully, because we’re clients, they they do.

But if we ever were in a client, I’d probably reach out and be like, hey.

Right.

And then the final question for you, Rachel, is if you were to turn back the clock and go back in time, what advice would you give to your younger self?

Oh, my younger self. My initial thought was like going back to like, first becoming VP. And it took me a little bit to realize nah, should be like our North Star. And now it makes so much sense and now it provides so much structure where originally I was like changing our objectives every quarter. It was just kind of like it felt fishy-fIshy. And now like, I love just like, well, obviously NRA should be our North Star. And then everyone under me, all of their objectives and I, you know, activities.

Did somehow impact the, the things that impact in our.

Yeah.

And so I wish I would have done that from day one. It’s definitely advice I would give to anyone in UX.

They also like that it’s okay to say no. Like I think we, kind of glossed over it, but my VP of revenue stint  I’m glad I don’t regret it because I learned a lot, but I wasn’t interested in owning sales. And 

I just wanted to say yes because I was asked. Yeah. And, I think it was just I wasn’t happy, you know, I just didn’t enjoy my job as much. So I learned a lot, though. So I’m not saying I regret it, but I think now I’m like, oh, like, I can actually, like, assess my own capacity and passion and like, what I’m good at and how I’m going to best impact the company. which now I just know, is it so?

So how did you find I mean, I know I said that was the last question, but then just the fact that you mentioned owning and running revenue and sales, but then somehow you didn’t like but then at the same time you own revenue for post sales.

I know the nuances. And why is it so different?

Well, okay, that’s a great question. So for me it was I mean it was like, okay, what’s the like mql to sales? Well to like, like all of these different rates and like, you know, Hiring a witch. Which I love hiring people. So that wasn’t as much, but it was like, okay, what do we exactly need to do to hit this number? And it was just like the mirror, like just being like, spread thin. Like I just had so many direct reports and like, I didn’t have the, the leadership layer underneath me that I needed, like, I had a lot of individual contributors, reporting up to me. And so it was like, oh, now I need to learn sales like and rev ops. Yeah. and, and I just, you know, like, part of it was just like, I want to do what I already know, like and keep improving that.

But I just, I felt like I never had a good hand. Like, I didn’t end my days feeling like I was, like, successful.

Got it. Yeah. Based on what you shared, I mean, clearly, this is me giving perspectives and Unsolicited advice based on like 45 minutes of conversation, but just based on what you shared. Rachel, it’s more like, as you said, a lack of leadership or leads who are experts in sales. But imagine if you had like a BDR or SDR team lead and a team lead, and then you get everything else day-to-day to them. Maybe you’re taking this on as well.

Agree, like if I had a director of sales or whatever that could own all the nitty gritty, like I was just pulled into so many weeds.

Yeah.

And needed to own executive strategy. So it was just it was. Yeah. But yeah I agree. Like if I had a good leadership structure underneath me, I would feel differently.

Improve your Go-To-Market Metrics through Positioning & Message Testing with Andrew Hatfield

Signature question: How do you view and define go to market?

Yeah. Look, I look at what we have, you know, our company has this business strategy of the things that it’s trying to achieve and the go-to-market feeds directly from that. It’s the strategy and tactical execution of, how you acquire, keep, and grow revenue-generating customers while also ensuring that you keep alignment of the metrics and the integration with that broader strategy across products, marketing, sales, and customer success. So I definitely see that go to market is an integrated piece with the overall, goals of the company. It’s not just something that’s that stand alone. I do see that in many places that it’s just marketing is off on its own. it has to be, you know, hand in glove with the overall business goals.

Yeah. And I love the fact that you called out product in there because at least 30, 40, or even 50% of the guests that I spoke with, inadvertently omit the product side of the house.

I mean, you talk about go to market, and if you omit product, that’s a big mess for me.

Yeah, no, I see it all the time. For me, I come from a technical background, so it just feels natural. But yeah, definitely, you can’t go to market without working with product, sales, or even Customer Success. It just doesn’t work. The more I do this, the more I study this field, and the more I talk to organizations that are growing and winning, the one thing that really stands out is that there is a tight alignment between those different functions. The teams that don’t have that alignment have issues. Yeah, yeah.

I mean, athletes, and often we keep hearing about marketing and sales alignment and our misalignment, if you will. Right? I mean, a lot of topics, a lot of chatter on social media and even offline forums and communities. But then how about the alignment across product marketing, sales and even supporting customer success? These are all functions that happen.

But absolutely, you know that this exact conversation of had many times in the past two months of yes, lots of people are acknowledging the need and the unfortunate reality of the the misalignment between sales and marketing. You know, like often you see sales. We hit our league goals. Yay! And you know I’m sorry. Marketing hit their league goals. 

But sales are sitting there going, I didn’t get good leads like I’ve missed my revenue number. I didn’t get opportunities from there, let alone qualified ones. And so like it’s good that we’re talking about this and that where we’re doing something about it. but similarly, we need to ensure that there’s alignment between the product and go-to-market. And, you know, like that communication has to go both ways. it’s not just product telling go to market. It’s not just go to market telling product, their partners right. Like that. 

There is this saying in product marketing that, you know, product management, builds the like, puts the product on the shelf, and product marketing gets it off the shelf, which is not great.

But in some respects, there is truth to that. Right? So, you know, you wouldn’t have a go to market without a product and you wouldn’t have a successful product without a successful go to market. So yeah, they’re equal partners just as marketing and sales are.

Yeah. And on that topic of misalignment or miscommunication, I often see product and marketing not talking often and early enough, especially when you’re looking to launch a brand new product or a major doing a major launch. It’s super important for the product. And more often than not, it’s product marketing. But the functions and teams have to work hand in hand from early on versus, hey, we’re one month out from launch, let’s pull in. Product marketing or marketing?

So many times product marketing is always fighting to get a seat at the table. And increasingly they’re being invited, which is which is awesome. I think that product marketing is the secret weapon that, more people would benefit from. and it’s not that product marketing wants to be there and take over.

Right. But there are skills that they have and, you know, the earlier in the product, you know, ideation phase that you can bring in those skills, the better. Like, there’s, there’s often this discussion about, you know, for early-stage companies, when what role should they hire first, should it be a growth marketer or a head of sales? I argue that if you don’t already know, you know your positioning, your story, your segmentation, what is it that those people are saying and to whom? So it doesn’t have to be that it’s a dedicated product marketing function, but the activities that a product marketer does need to be there. it’s like the foundations of business, right? It’s not nice to have if you don’t know who you’re selling to and, and why they should care that that that’s not it’s not optional. Yeah.

Very cool I know we’ll be getting into more of these topics in the conversation later on. switching gears and big picture conversation and more around you.

Like what’s your career journey like and what led you to what you’re doing today?

Yeah, so I actually started my career in tech. You know, my parents owned software companies. And so, I started as a programmer. I loved that. And then I really fell in love with, like, deep technical, like, operating system stuff. I became a systems engineer and moved my way through that career into solution architecture, then into pre-sales and sales overlays, and eventually into product marketing. And now here I am running our product marketing and growth agency, Deep Star Strategic. the thing that like, really drives me and like how I’ve moved through those kind of like three big bucket stages is I’ve always had this understanding that like the, the technical thing that I’m doing is to support the business. So, you know, when I was writing you know, applications. It was business apps. Not infrastructure or IT apps. And so it had a direct impact on invoicing or the ability of sales folks to, you know, process an order or find inventory.

Excuse me. and so I took that same view when I was in that infrastructure role of like, yes, the infrastructure was super important, but it supported the applications which supported the data so that the business could actually function. And, you know, taking that even further of excuse me and taking that even further to, you know, the businesses there to serve their customers problems. So like this, this theme has just really been with me the whole time. And so, I remember, you know, when I’d start working with a new salesperson in, in pre-sales or even, you know, as a sales specialist and overlay, I’d always like, sit them down first and say, look, Tim, we’ve not worked together like I hear great things about you, but I don’t work like most of the other people. Like you’re going to sit there in this meeting and think, what are you doing, Andrew? You’re going around this, you know, garden path, like get to the point.

But it’s always about how can I really uncover what I now know to be unmet needs in the jobs-to-be-done framework. So it’s really that that focus on what it is that we’re trying to do and why that matters. And I think the thing that’s really helped me be able to do that, like my overall career, like I’ve constantly been told, Andrew, you need to specialize and be like this expert in this one thing. And I’ve just always pushed back against that. I have been a really strong generalist, there are absolutely people who are better than me in every area that I touch, but I am fairly deep in many of those areas and have a good knowledge in more so that I can go and get the right resources or I can build the right team. Similarly, taking that same sort of approach to work for small businesses or work for enterprises, I’ve worked for end customers, I’ve worked for vendors, I’ve worked in the channel, and I’ve worked for the public sector.

Yeah. And so the thing that I think really sets me apart and has been able to, you know, drive my career is just having a really good understanding of my customer, of how they operate, what their lives are like, why they do the things they do, like how they do them. and that’s helped whether I’ve been in it in, you know, sales, marketing, or now as a business owner.

Yeah. No. Very cool. Yeah. I’m looking at your LinkedIn profile and as you said, right early on in your career, you started off as an engineer and then you moved on more into architect and solution architect roles. But then something happened. While you’re at Red Hat, you’re doing and playing the role of a solution architect. And then you moved more into sales, pre-sales based dev So talk to us about that transition and what prompted you or what what motivated you to make that move.

Yeah. Look, I loved my time at Red Hat. Built some really good relationships.

really interesting place. Certainly, at that time, it was going through a lot of growth. And. Yeah, like, it was just. I’ve always wanted to do more. Not that it was like, what’s the next thing? And, you know, always trying to jump, but how can I be more effective? How can I help the customer? 

More so like every time I learn something in, say, software development or in infrastructure or architecture or then into, you know, looking after, you know, a product set in a, in a country of like, how do we, you know, sell this and grow it? It just kept expanding and like, it really is that paradox of knowledge that the more I learned, the more I realized there was to learn. And I always felt that to be better, I need to know these things. And so I’m a fairly determined person, and so I just, you know, continue to, to chip away at things. And, you know, I’d go and sit with, sales, like being a pre-sales architect.

It was, obviously you supporting, account sellers. And then because of that, ability, like, I’d been learning how to sell, I was very deliberate because it’s just it wasn’t originally something I was I was good at, I learned how to do that. And, ended up, you know, being in 100% club, you know, six out of the, seven years that I was at, at Red Hat because I just like, what is it that the customer is trying to do? And how can I connect this product and this thing to that? And just being really focused on that.

Very cool. And then after Red Hat, you moved into a product marketing and marketing side of the house. but something else I noticed is at NetApp. It was a mix of like business strategy, go to market. So tell us about that role and your experience being head of cloud strategy over there.

Yeah. Well, just to make that make sense, as I was moving my career through Red Hat, I really wanted to be involved in building something.

And so, you know, I was looking at product management roles and then, like, internally and externally. and I remember distinctly being in this hotel room because I was traveling, 70% for Red Hat at that point. and I had this call with, editor Sue at, at, at the time, mesosphere then Duke, he was head of he was vice president of product management and product marketing at mesosphere. And I’d applied and, you know, made it through to the final round for, a product management role. I was just talking to him, and he’s like, Andrew, I really think you’d be more of a product marketer. And I’m like, no, no editor. And we went back and forth things like, Andrew, I really think with your, your, focus on the market that product marketing is, is really what you want. So I took the hint and got the job. And, that was a fantastic learning experience. I love working with it. It was, it was it was hard, but just fantastic.

And so, again, like the, the, the work at NetApp, similar sort of story. Right. The same sort of reasons of how can we do that, but just at more scale. Right. So, yeah, I’ve, I never felt that I was naturally good at strategy. I think I gave myself a bit of a, a hard time there that, yes, obviously I’ve learned a lot of things, but, as, as I think through, like, how I’m, relied upon, it’s largely because of that ability to see the bigger picture of how things come together. And definitely part of that is the career history I’ve had, like in those different organizations, in those different roles and the different viewpoints that have those similar aspects. So yeah, that’s that’s how we kind of ended up, being that, you know, strategy, how do we scale? How do we take a product to market?

Yeah. And when anyone talks about strategy or their role involves a lot of strategy, I go a bit crazy.

I feel a bit uncomfortable because, okay, so cool. It sounds very sexy. Very cool. Don’t get me wrong. but then how are you actually showing the value of what you’re doing for the business? So my question to you, Andrew, is like, what KPIs or what were you measured against in that role?

Yeah. Look, I agree with you that too often strategy is pontificating in your ivory tower. And definitely there there are some good things that come out of that. But strategy without execution is just, you know, talking or it’s a piece of paper that sits in the bottom drawer. So, I’ve always looked at, okay, what is it we’re actually trying to achieve while it’s hit our North Star metric, it’s. Which then leads to revenue, right? revenue is the outcome of that. Yeah. so what are the things that we know lead to hitting that North Star metric? So, like in the case of NetApp, it’s storage under management. Right. Like it’s how much capacity a customer is consuming.

And so or how do you how do you look at the leading indicator for that? While it’s the sort of applications that you support for their business, like what use cases are you aligned with? what teams are you talking to? you know, what partners are you working with? And then like, from there, obviously there’s, there’s the, the, the traditional exile’s metrics of like, pipeline. you know, share of voice. and then obviously, how much of that converts? Yeah.

Got it. Pretty cool.

And then, you decided to take a completely different route and went on your own. So talk to us about that transition and the motivation again.

Yeah, it’s cool. Like, I did have, my own business, you know, back when I was. I can’t remember now, I think around 20, doing, you know, it security and network security. And look, that was that was an interesting learning. built a decent product, but just didn’t have the business experience, I wasn’t ready.

So this time around, like, really focused on how can I apply everything that I’ve learned, you know, without, like, over boiling the ocean? Yeah. And, yeah, like, it kind of started as a, you know, working full time. And, you know, what can we do on top of things? I had started just before Covid and then, yeah, Covid hit and it’s like, oh, wow. Yeah, things aren’t exactly going to plan. how can I make sure that I’m not just completely subservient to all these other things in the market? You know, the classic rich dad, poor dad of, you know, being an employee? you know, you’re at the whim of everyone else. 

So how do you then move from employee to small business owner so that you can build a big business? Yeah. yeah. Like taking those sort of thinkings and, you know, started as a, you know, I’ll do a contract here or do a contract there and just kind of grew and grew and grew and then, you know, the needed more people.

And, you know, the company sort of grown. It was more than just me. So, yeah, like, we’ve tried to be deliberate and balance organic with, driven growth.

So got it. And what what do you guys do at, Deepstar Strategic? What are the services and what kind of clients do you work with?

Yeah. So effectively, like, if you boil it down, like we use lots of pretty words, but it’s product marketing and growth and the looping back to the beginning of this conversation, a large part of it is ensuring that go to market has that closed loop and integration across, you know, product marketing, sales, customer success with emphasis on the product to go to market side. we feel that that is definitely a strength because of, you know, in particular my background, but, similar the people that we, you know, have in our organization have those same sort of experiences. Yeah. but it’s also like that understanding of how customers buy and how it’s changing.

You know, the world is very different to 2020. Like we hear that all the time, but we kind of forget that it’s even more different than Then 2018 and 2012, and a lot of the playbooks that businesses rely on are built on the assumptions of a world that no longer exists. And so, again, aligned with background, we focus on on B2B. I don’t know a lot about B2C, so it’s B2B, it’s SaaS in the vast majority of cases. You know, we’ve got a very strong belief that the future of software is at the minute, as a SaaS delivery, and with a particular focus on, tech, SaaS, not not everything, but not necessarily like IT infrastructure, but like you’ve got a technical product. and that could be, you know, something like you have a, an aerial survey company using drones so that building management can, you know, look after their facilities, like we classify that like you’re using technology to, to build a product and a business.

Yeah. Primarily focusing on growth-stage companies. like, obviously we have a lot of interactions with earlier stage, you know, seed and really early start-ups, but a lot of like a lot of what we offer really fits that that growth stage where, okay, I’m now at a bit of scale, I’ve got some product market fit, but I’ve started to, you know, run into either some scaling problems or I’m now wanting to expand my segments or, you know, add on a new product or enter a new market or of now started to, you know, kind of hit that ceiling of, paid ads was great. And now it’s okay. That’s not enough. Right. So how do we tune that? In particular, lately, it’s been about how can we identify wasted spend so that everyone’s budgets are being cut. And often we see that you know, you know, go to market leaders, in particular, are just like, okay, your budget’s cut by 30%. We just cut everything by 30%. 

Done. Yeah. And sure that that meets your internal, direction, but we know that that’s not going to be sustainable, right? Because there’s always at least, you know, 20%, often 40% of your spend. That’s just ineffective. And the problem is a lot of companies don’t know what’s ineffective, because again, going back to this, knowing your customer, and this isn’t necessarily just an argument about attribution or recognition of, you know, credit of like who brought in the opportunity, but what works, right? 

And, you know, like I said, the way people buy now has changed. But a lot of the playbooks you look at waterfall, you know, the demand waterfall, it just doesn’t take that into account. So lately, a lot of what we’ve been doing is helping businesses apply that understanding and then identify spending that’s completely wasted. Yeah. And often they’re like, oh, I’m not sure if I want to go and cut that program and like, cool, why don’t we just

reduce it by a little bit for a couple of months? And often like nine and a half times out of ten, that program is ineffective.

There’s no change to any of the other metrics other than it going up. And so we’re able to say, look, why don’t we cut that a bit further and we’ll redirect that spending to something that is actually working will multiply that. And so, you know, helping customers with that ability to do less with less with a better result.

Yeah. And so pretty cool. So you’re helping them around their marketing budget and performance, marketing budgets, and so on. So who would you categorize or who do you see as your primary ICP the CMO, VP, marketing, growth marketer, CEO, or someone else?

Yeah. So typically we’ll focus on a B to D style, startup or that bigger enterprise where we’re working more with like a product division. at that larger side, it’s often the product, you know, revenue marketing or you know, sometimes performance or demand. Gen. Yeah. for that particular product line for the growth stage startup, you know, B2D typically it is we, we enter with the CMO and often talking with the head of sales.

Yeah. some startups still have the founding CEO, you know, sign off on everything. And so, you know, we build relationships, but most of the time the entry point is, is CMOs, for that particular, you know, service that we, we have, when we’re talking more around holistic go to market, definitely including more, you know, head of product, Chief Product Officer, as well as, you know, customer success and sales. But often that’s, a secondary engagement because like, that’s more of a it’s seen as a vitamin. I know that that is, is critical, to growth. But like immediately the pain that hurts the nail in the, the forehead that is, is, you know, keeping me up at night, which I hate that phrase, but the pain that they’re really suffering is all right. I’ve got this budget. How do I spend it to make sure that I keep my job right as a CMO and, you know, make sure that the spend is effective so that we actually generate revenue, customers, paying customers?

So yeah.

Very cool.

So, Andrew. Yeah. Thanks for walking us through your career transitions and the different motivations, as well as the services that you provide, with, your company today. on a lighter note, I mean, you’ve been through a lot. You’ve been through different stages and different roles. how does your family describe what you do for a living?

Earlier, it was Daddy living on a plane. thankfully, like, 70% of travel is over. But, you know, I even asked my wife about this, and it’s like, well, we really don’t know, but we know you get up and work insane hours and you help companies, you know, help their customers. Yeah, that’s about it. It’s like some marketing thing. so the, you know, I’ve got some, some young kids, you know, you know, 12 to 7. They’re very inquisitive. They think it’s really cool that daddy talks to lots of people around the world and, you know, balancing that business and tech and, you know, like, the kids would come to me and try and tell me about how things work on their iPad.

And I’m like, sweetie, you know, daddy used to work for the companies that build that thing, like Roblox used to be a client, like, no. So that that look on their face or like when they’re trying to tell me, like, I know there’s something wrong with the App Store and they can’t, you know, go and get an update. It’s like, daddy, do this. And it’s like, thanks, buddy. daddy used to do this stuff. So, they’re constantly amazed, which is amazing. I don’t expect them to understand everything. but yeah, like, it’s daddy does some, some cool stuff to, to help other people do their stuff. Which which I think is nice.

Yeah, that was very funny. I mean, hearing your wife or kids say, hey, that used to be on planes and he’s always traveling versus now they see the other side. Which is your app working with clients from all over the world. So that leads me to another question, which is like, where are your clients mostly based out of, and how do you manage the whole time zone difference, given that you are in Australia and in Brisbane?

So when the joke at Red Hat, even though I look after APAC, was that Andrew never sleeps, which was not true. just clever marketing. and internal, relationship management. when I left Red Hat and started working for Mesosphere and a number of other Silicon Valley, startups, you know, I’m in Brisbane, I’m in Australia. It’s an 18-hour time difference. I often joke that I’m from the future. Sadly, it doesn’t help me with the stock market. but, you know, that has challenges, right? Like America and North America is the world’s largest market. That’s where most of the tech firms are most of the people that I would look at as either clients or potential partners. And so I just decided that I’m no longer going to be a night owl. I’m going to be an early bird. And so I get up for a 4 a.m. local start to align with, you know, 10 or 11 Pacific. Yeah. and that’s worked really well. Like, I was surprised the first couple of months was really difficult.

But I’ve been doing this for six, six years now, like that, those sort of working hours, it gives me incredible freedom to work with great people, but also still have a lot of balance with, with family. Like, I go to the gym in the afternoon, 3 or 4 times a week. I can pick up the kids. so that’s really good. That actually, like, the weird working hours actually works better for our family. you know, working from home helps as well, right? In terms of the clients, look, a lot of them are in the US. some of them are, you know, every now and then, like we’ll get a European customer, which is great. That does mean it’s it’s often late hours for for face time. but, you know, one of the things, you know, when I decided, you know, deep star strategic is going to be more than kind of like a side hustle where I do some contracts and like a real business.

The, founding like philosophy was there are so many great ideas that fail because they can’t execute. And for some of that, it doesn’t matter what go to market is, it’s just not a viable product or company. Right. but those that are like, there’s still a large number that fail. And so a lot of the time it’s because you’ve got, people that are great at the thing but don’t understand or have those skills of how to actually grow the business. 

And so how can we help them? so there is like a real soft spot for an Australian audience and a lot of, you know, Australian startups like we really do like punch up and, punch above our weight. in terms of, you know, the relatively small talent pool and capital in Australia compared to North America, like we’ve got some great companies. Like there’s Atlassian, there’s there’s Canva, Safetyculture, you know, Xero, like their global brands. And often a lot of those companies as they look to scale, from Australia, want to serve a US market.

And, you know, we have a lot of experience in that. So, look, we aggressively go after and focus on the Australian market. but a lot of our clients, just through the nature of where they are, are in the US, and we find that, that again, that, that, that diversity, not just from a business risk perspective and, and revenue, but just keeping your hand on the, the pulse of what’s happening is, is really good. And obviously, the experience of having worked across Australia, Asia Pacific, and the US, is something else that differentiates us in the local market. conversely, American companies that want to enter the Asian market often, you know, North Americans kind of see Asia as just one amorphous blob that looks the same. It is very different like it’s very different to Europe. there are not just lots of countries. There are lots of time zones. there are lots of different cultures. You know, you look at, a lot of Asia, like Japan in particular.

You have to go through partners. The same in Vietnam, and Thailand, very similar in Singapore. but then interestingly, like in Japan, the customer cares about their relationship with the partner far more than the vendor. And so there’s a lot of these things that are so different to how business works in North America that, you see a lot of companies fail in the. Yeah, the Asian expansion. Yep. So, yeah, those things help too.

Yeah. No. That’s good. Good. Getting a wide perspective, starting from how you plan your day and working with the different time zones, and giving advice to folks who are looking to enter the Asian market. switching gears here, as you and I know, Andrew go to market is not just success or not just failure. It’s going to be a mix of both. So if you can share a go-to-market success story and a failure story, I’ll let you pick which one you want to go with first. Yeah.

So, a success.

so I won’t use any names. because there’s, there’s obviously details, but, you know, a large tech company that we’re working with, they were successful in their own right. They had a good and growing product that was in a cloud, you know, hyperscalers marketplace, which, you know, was good. However, the third-party marketplace introduces a lot more hurdles to an end customer. Like there’s there’s different billing, there’s different contracts, there’s different procurement. 

You can’t draw down on the cloud credits that, you know, you go and get a contract with them like it’s a separate, amount of money, you know, supports different. And so that was starting to hinder them. And so, you know, working with them, we’re like, okay, why don’t we see if there’s appetite with the, the cloud provider to make this a first-party service, which is a massive hurdle. So, you know, that that kind of snowballed and, had a lot of like, senior executive, you know, up to the point of, you know, CEO conversations between, you know, those two parties and moving big machines is really hard.

And so, just trying to make it, you know, okay, cool. Like, we’ve got this big dream, but like, let’s just, like, make sure we’re getting this done. Yeah. and so, yeah, like, last year, working with them to take that product as a first-party service. So it’s now like owned and operated by that cloud vendor, or there’s joint product and joint engineering. there are individual and joint go to market. you know, sales enablement is joint and individual. They both have sales teams, but there’s a lot of like they work together. because there’s obviously more than what that other company sells inside of, the cloud provider. like that, that that was really hard. 6  months later, there’s still a lot of work to do. This is still a teething problem, as you can imagine. Like that. That’s not an easy thing. but, you know, like a lot of those customers that were on that third-party service, you know, transitioned, which is good because, you know, enterprise companies, you can’t just, you know, announce to them that, oh, hi, we’re completely changing how you consume the product.

And can you do it tomorrow? Right. so that’s really good. So the feedback from both existing customers and net new. And so there’s good growth on that side as well. and yeah like that’s the the the growth rate is significantly higher from the the first party side to the, the marketplace, which was the goal. So things are all moving up to the right.

Very cool. And then what were your services and what did you specifically do? Was it more around alignment or, did you create content or collateral? So talk.

Yeah, a lot of so I was involved in that project. So a lot of what I was doing was around the content collateral and the joint selling efforts and that sales enablement and some of it was like helping educate customers around. Okay, so this is what’s changing why, and what you get out of it. Yeah. Other parts were okay just simply because we now have this co-engineered product. What. That opened up a whole heap of other avenues that we could, you know, build solutions for or use cases that we could serve that just weren’t available before.

And so okay what are those like identifying them and then prioritizing them both in their market opportunity and the ability of the sales teams to execute? and, you know, building, the collateral for that. So whether it was, you know, sales decks, you know, working with the revenue marketing team around campaigns, some of their other partners that they used, like, how do we involve the, the end like sales channel. partnerships that were, you know, partners, on both sides. So, yeah, a lot of the more on, the sales side, in terms of the execution.

Very cool.

And the salespeople are great Yeah.

So the other part of my question was a go-to-market failure story. And again, as you and I know, there’s nothing like a failure. It’s more of a feedback loop or a lesson. So if you can share a good idea that didn’t really pan out as planned.

Yeah. So a couple of years ago, I worked for a North American, I suppose you’d still have called them startup.

They were looking to IPO. They eventually got acquired. they had been the market leader for many years in, in IT automation. And I had some experience doing that, with a competing product at Red Hat that kind of helped dethrone that company. So it was really interesting. going to the other side of what was the leader then started to lag. I joined them because it looked like they were like trying to do some things to turn this around. And they wanted help. They wanted that, that other perspective. and so that that seemed so promising. 

And there was definitely eagerness on the south side to kind of stem that tide and tell a more modern, up-to-date story. But even with a new head of product that was very experienced, there was still a lot of reluctance on the product side to, you know, just acknowledge that the impact to technology that cloud has had and how it organizations in particular, you know, now run their ops, let alone the integration of, of dev and then DevOps.

So that was really difficult, that there’s no point in telling a story that you can’t deliver on. Like storytelling is super powerful, and it allows you to set a bigger picture that you can take your buyer or customer down, you know, nine out of ten steps, but you can’t, you know, get over your toes too far. otherwise, it’s the vaporware. And like, you lose credibility so you can set a big vision as I look. We can take you three-quarters of the way, but we’re like, in the next two quarters, we’re going to finish it. Right. And as long as you deliver on that and you’ll, upfront, that’s okay. But yeah, there was such a big difference between the stories that we wanted to tell that we, you know, you know, smart technical people that, you know, been in that segment for a long time and, you know, others in the go to market team that, you know, okay, this is what customers are telling us.

Yeah. There’s still such a big divide between that and, you know, product and engineering. what’s even more unfortunate is they had this whole new idea in a product that they had started, but it was then driven by the CTO. It was outside of product and, like dedicated engineering. And that was amazing. Like that. 

That was all around like helping infrastructure teams operate in an event-driven manner rather than a procedural which has so many possibilities. But it was really treated like a science experiment. And I’m like, hey, I know this is weird. Like, this is different, but like, there’s an opportunity here and like connecting all these dots and like, you know, showing them, you know, giving the leadership team the, the details of customer interviews that we’d had or showing them like, this is what the impact would be from a technology side and how that would translate into, you know, growth for the company. And they just didn’t see it like that. That was not the world that they were in.

And so I would count that as a failure of me to be able to, you know, lead those executive teams. But, you know, it’s it’s also hard. And this is the flip side, right, of alignment. You can’t talk about alignment and preach it and then be the one that goes rogue. Right, right. Like as much as you back yourself and you think you’re right, you know, as much as you might think that you’ve got all the information at hand, you know, often you don’t. And, you know, like I would say in this case, it’s unfortunate that that was amiss. they ended up, you know, like I said, getting acquired by a PR firm. yeah, I think there was heaps of opportunity there. And I would say that that was partly me, partly the market, approach that, that leadership wanted to take. Yeah.

Very good. Yeah. Practice what you preach definitely applies to go-to-market marketing, sales, alignment, or alignment across any functions for that matter.

And equally applies to parenting as well.

Yes, as much as you like, but I know. Yeah. yeah. Look, no one, you know, has all the answers. And like, while I do have that, that breadth of experience, the thing that it has taught me is you need the people around you and you need to take them with you, or you need to be going with them, right? Like. Like I said, you can’t go rogue, no matter how well-intentioned or justified you think you are. So.

So in terms of staying up to date, when it comes to go to market, like what people, community resources, books, podcasts, or anything for that matter, what do you lean on?

yeah. So I love to learn. I am constantly interacting with, you know, people that I think are less experienced or more experienced or smarter or, like, just I want to learn from everyone. so a lot of LinkedIn and LinkedIn and, and X or Twitter, there’s great conversations in those places.

I like to, you know, I’m, I’m a big contributor to the Product Marketing Alliance. I’m an ambassador there. And so that’s been really helpful, just getting access to a lot of other smarter people. And, you know, I kind of have a couple of podcasts that I like listening to. Like cheekily, I do quite like yours. so love that I’m here. That feels really awesome. you know, Dave get hearts, you know, exit five podcasts. Jay closes, you know, creators. but yeah, like, how can I get views and experiences from people that are adjacent to what I’m doing, that are doing the same things that I’m doing or touching and sometimes just completely different? 

Like I remember years ago, like I was I was a young adult, you know, I was at uni doing, you know, an IT degree and, software engineering and, data communications. I was a young boy that, you know, played on computers and, you know, mucked around like a little bit of games, but lots of like, how can I go and improve the Linux kernel? very aspirational.

and then, you know, like my world just revolved around tech. I was working full-time in tech as well, and like, I wanted something different. So I went and became a waiter at a busy cafe. And so even that, like, made me better. So I’ve definitely got this understanding that there’s lots to learn from outside, the field you’re in. So, you know, one of my mentors, he’s an Olympic Stadium architect, like I’ve learned so much from him. Has nothing to do with the fields that I’m in. And yet the lessons have, you know, massively multiplied my income in the last, you know, ten, 15 years. So, you know, just that appreciation that, yes, you want to take in lots of things and filter them, but also not limit yourself to your domain. So. Right.

Yeah, I’m glad you actually touched upon that point right when I asked you for resources and a community of people that you lean on, I’m glad you touched upon.

Hey, it’s just not this domain. And more often than not, I do that myself, which is I listen to the podcasts that are outside of or have nothing to do with go to market. Maybe it’s about writing, maybe it’s about presentation, maybe it’s about entrepreneurship, or maybe it’s about finance. Completely different topics, or just having fun conversations on very topics. And that’s really critical, especially to wind down and give that rest period to your brain for more ideas to formulate.

Yeah, absolutely. There are a couple of things you hit on there that I agree with, right, that you need to have that balance. Like just knowing everything about one thing makes you a dull boy. And so just personally, you know, when you’re talking with friends or trying to socialize, you’re boring, like have other interests. like, I love to barbecue, I love to cook, I love to snowboard. you know, I work out a lot with a lot of, weight training. lately, I’ve been learning about the carnivore diet.

That’s what’s been working. But, yeah, I love meat, but can’t just have steak and eggs all the time. So, like, what

else does that involve? so. Yeah, and like, like, we, we kind of, I think we’re arguing in furious agreement about you will be better at the thing you do by learning about other stuff as well, because there’s lessons that are applicable universally. Yeah, for sure.

And a final question to you is if you were to turn back the clock and go back in time, what advice would you give to your younger self on your like on day 1? If you go to market journey.

No matter how fast you’re moving, you can always move faster and learn faster. don’t try and like do everything at once. And so like in line with that. Like moving faster. do it with smaller steps and like, really focus on on connecting those dots between things. I think that’s, the thing that I would say, like I am even now, like whenever we run a new campaign, I’m amazed that it works.

I don’t think I’ll ever get over that feeling. I think it’s so weird. Like, I’ve done this a while now and I’m still amazed. Right. and, like, you know, my career, I’ve been working since 96. across all those different areas. Like, I’ve learned a lot of stuff. And even there, like, I’ll still, like, talk with my wife, like, I got, like, this much done today. and like, I, I recognize this. I don’t know how to get over this, but I’m just constantly blown away by just the, the, the the speed and the volume of output that I’m capable of achieving And, you know, I don’t expect that of everybody. Like I’m the CEO, the business owner. Like, it’s, like my baby, you know, people, you know, work hard, but, yeah, just constantly amazed by just how, how much that you’re able to get done. but, the lesson really is knowing how to identify what the right work is and just do it faster, and learn faster.