From Oracle and SAP to Founder to Stanford: Holly Roland on Building GTM That Compounds with AI
In this episode of the B2B Go-To-Market Leaders Podcast, Vijay Damojipurapu sits down with Holly Roland, former executive at SAP and Oracle and founder of Rebel GTM, to break down what go-to-market really means in today’s AI-driven world.
Holly introduces a simple but powerful framework: go-to-market is an infinity loop of discovery and value, where buyers move from awareness to purchase, and then into expansion, cross-sell, and advocacy. Yet most B2B companies still over-index on acquisition while underinvesting in the value loop.
Drawing from decades of experience across enterprise tech and startups, Holly shares how she evolved from product management into go-to-market leadership, and why she ultimately built Rebel GTM to help companies align product, marketing, sales, and customer success into one unified system.
They dive into:
Why go-to-market should be viewed as a discovery loop + value loop, not just a funnel.
The common mistake B2B companies make by prioritizing new logos over expansion.
How marketing alone can’t fix growth if upstream and downstream functions are misaligned.
Career lessons on moving from IC roles to leadership through collaboration and influence.
Why storytelling and positioning are as important as the product itself.
The rise of Generative Engine Optimization (GEO) and how it’s reshaping digital presence.
A real-world GEO case study that improved readiness from ~30% to nearly 80% in weeks.
Why LLM-driven traffic produces higher-intent, higher-conversion buyers than traditional SEO.
The importance of reframing your product to match how customers think (not how you describe it).
Practical ways to approach AI in GTM; starting with workflows, not tools.
Holly’s core message is clear:
Great go-to-market isn’t about isolated tactics. It’s about aligning the entire company around how customers discover, buy, and realize value.
This episode is a deep dive into modern GTM strategy, combining foundational principles with emerging trends like AI and GEO that are redefining how companies reach and convert buyers.
How GTM Teams Win More by Moving Faster with Kris Rudeegraap, Sendoso CEO
In this episode of the B2B Go-To-Market Leaders Podcast, Vijay Damojipurapu sits down with Kris Rudeegraap, co-CEO of Sendoso, to explore how modern go-to-market teams are evolving beyond traditional sales and marketing and why agility, creativity, and customer experience are now the real drivers of revenue.
Kris shares his journey from early entrepreneurial hustles and sales roles to founding Sendoso, a category-defining platform that transformed direct mail and gifting into a scalable GTM channel. Along the way, he reveals how identifying untapped channels became his competitive advantage and how that mindset shaped Sendoso’s growth.
The conversation dives deep into how GTM has shifted from a top-of-funnel obsession to a full lifecycle strategy, where post-sale expansion, customer engagement, and advocacy play a critical role in driving sustainable growth.
They dive into:
Why go-to-market should include post-sale expansion, not just top-of-funnel acquisition.
How the “growth at all costs” era led teams to ignore retention—and why that’s changing.
The origin story of Sendoso and how direct mail and gifting became a breakout GTM channel.
Why finding unsaturated channels creates unfair advantages in outbound.
The three core GTM levers behind Sendoso’s growth: outbound, events, and content.
How community and advocacy became a powerful, compounding growth engine.
A real GTM success story behind Sendoso’s Clay integration launch, generating millions in pipeline.
The shift from large SDR teams to AI-enabled outbound systems that produce more with fewer resources.
How to think about AI agents, org design, and system redesign in modern GTM teams.
Why agility—launching fast, killing what doesn’t work, and pivoting quickly—is the defining advantage today.
Kris’s core message is clear:
The future of go-to-market belongs to teams that can adapt faster than the market itself.
This episode is a masterclass in building a modern, adaptive GTM engine, combining creativity, systems thinking, and AI to stay ahead in an increasingly noisy world.
In this episode of the B2B Go-To-Market Leaders Podcast, Vijay Damojipurapu sits down with AJ Gandhi, Chief Growth Officer and Go-To-Market Operating Partner, to unpack what it really takes to build a high-performing, holistic GTM engine.
With a career spanning Bain, McKinsey, venture-backed startups, Salesforce, RingCentral, and private equity, AJ brings a rare 360-degree perspective on strategy, sales, marketing, partner ecosystems, and post-sales execution.
AJ defines go-to-market as the entire lifecycle journey of a customer — not just sales — and explains why most companies underperform because they fail to integrate product, marketing, sales, partners, and customer success into a unified system.
They dive into:
Why GTM must be holistic across the full “bow tie,” from acquisition to expansion and advocacy.
The diagnostic framework AJ uses to assess strategy, talent, execution, and performance in portfolio companies.
How to identify waste in sales coverage, geography expansion, marketing spend, and organizational design.
Why partner ecosystems follow the 80/20 rule — and how doubling down on top partners drives disproportionate returns.
The importance of measuring value realization, not just selling ROI promises.
How to elevate mid-level business problems to CFO-level strategic priorities through economic impact framing.
Lessons from scaling enterprise and mid-market GTM motions — and the danger of straying from your ICP.
Why pricing optimization and expansion within existing customers often deliver faster impact than new logo acquisition.
The leadership discipline required in the first 100 days of a transformation.
And AJ’s advice to rising GTM professionals: master the fundamentals, focus on the 80/20, and develop influence without authority.
This episode is a masterclass in combining strategic rigor with execution discipline — and a reminder that sustainable growth comes from fundamentals done exceptionally well.
In this episode of the B2B Go-To-Market Leaders Podcast, Vijay Damojipurapu sits down with Joseph Sirosh, Founder & CEO of CreatorsAGI, to explore how go-to-market strategy fundamentally changes in the age of AI, and why trust, differentiation, and customer clarity matter more than ever.
With nearly three decades of experience leading AI initiatives at FICO, Amazon, Microsoft Azure, Compass, and Alexa Shopping, Joseph shares rare behind-the-scenes insights into how AI products actually make it to market, from early neural networks and fraud detection to today’s agentic AI systems.
The conversation spans founder-led sales, product-led vs. sales-led growth, and why AI forces companies to rethink how customers discover, evaluate, and trust complex products.
They dive into:
How Joseph defines GTM as ICP clarity plus differentiated value, not tactics or channels.
Why GTM is never static and must evolve alongside product and customer maturity.
The role of trust in B2B buying, and why buyers are betting their careers on your product.
Lessons from selling AI at hyperscale versus starting from zero as a founder.
Why product-led growth resembles DevOps for go-to-market.
When sales-led growth is unavoidable and why complex products demand partnership selling.
The early pivot from creator-focused AI to B2B agentic AI at Creators AGI.
A real GTM success story showing how AI agents cut sales cycles in half.
Why customers can’t always tell you what AI product to build, and what founders should do instead.
Practical advice for founders building GTM motions around emerging, fast-moving technology.
This episode is a masterclass in AI-native go-to-market strategy, blending deep technical insight with real-world GTM execution from one of the industry’s most experienced AI leaders.
IIn this episode of the B2B Go-To-Market Leaders Podcast, Vijay Damojipurapu speaks with Akshay Doshi, SVP of Sales at SpotDraft, about building repeatable value in B2B SaaS—and why great go-to-market is ultimately about elevating customers, not just closing deals.
Akshay shares his journey from SDR to sales leader, including formative lessons from customer success, enterprise account management, and scaling sales teams during uncertainty—most notably, building SpotDraft’s GTM engine just as the pandemic reshaped buying behavior worldwide.
The conversation explores how modern GTM leaders can design sales motions that mirror the customer experience, create trust through expectation-setting, and build systems that scale culture—not just revenue.
They dive into:
Why Akshay defines GTM as go-to-repeatable value, not just pipeline or quota.
How experience in customer success makes sales leaders more credible and effective.
Designing sales processes that reflect the onboarding and delivery experience customers will actually receive.
Building trust by saying “no” to the wrong customers—and why it pays off years later.
Scaling a sales culture through values, micro-wins, and cultural carriers.
How sales and marketing must operate as a single orchestration layer, not separate functions.
Lessons from scaling SpotDraft through outbound, word-of-mouth, and customer love during COVID.
Why AI in legal tech requires careful expectation-setting, not hype-driven positioning.
Advice for aspiring GTM leaders: learn adjacent functions early and think like an operator, not just a seller.
This episode is a deep, practical look at how modern sales leaders can build durable GTM systems by aligning value, culture, and customer outcomes.
From SDR to SVP of Sales: The Go-To-Market Thinking Behind Akshay Doshi’s Rise
Article:
Standard signature quest. And I know you’ve heard the podcast, so how do you view and define go-to-market?
Indeed, I have, and you know, I really do enjoy this question. I’ve heard a bunch of leaders on the podcast talk through various definitions of it, and every time I hear a definition, I’m like, Damn, that’s good. Damn, that one’s also good. And when I was thinking about it, just to simplify, go to market. Really, to me, what it really means is go to value. And specifically go to the repeatable value. And the funny thing is that the definition of value constantly evolves as tech evolves, as time evolves, what people consider to be valuable evolves as well. So in that sense, go to market is an ever-evolving thing too. So go to market repeatable value is like what I would say, how all teams come together in a company to make sure that we’re elevating the customer. And that’s that, to me, is I go to market and I talk a little bit about the philosophical side of it. It ties into one of the values that we have here at Spot. Drafters elevate each other. So in a sense, when you’re when we talk about go to market and go to values like, how do we use, bring our product, service, anything to the customer, to elevate them?
I love that definition, go to market. But go to, sorry, you mentioned something,
Yeah, yes. It’s go to repeatable value. Is essentially the cracks of it, yeah, yeah.
Got it, yeah, my bad, yeah. Go to repeatable value. That is actually an interesting I never heard that before, by the way, Akshay. Go to repeatable value. I know what you’re trying to capture in there, which is, to your last point, which is one of the core values of your company, which is, how do you elevate, yes, your customer. Of course, you have to elevate each other internally in order to achieve that, elevate others, or elevate the customer, right? But go to repeatable value. You’re spot on, by the way. I’ve heard this from so many. Go to the market leaders. Where it is, it’s almost, I mean, in a product world, it’s very clear that you have a product roadmap and a product version one, version two, version three. But somehow, that notion, that terminology, is not carried over to the go-to-market side of things. But to your point, it is iterative. It’s never a constant. Because market dynamics can change how they value and see your product, and even internally, so many things can evolve and change.
Yeah, that’s exactly right. You know, at the end of the day, it’s an alignment system across sales, customer success, marketing product, they all need to be talking to each other to create, communicate, and capture value.
Yeah, excellent. I’m sure we’ll dive into a lot of those topics in the next 45=50 minutes that we have? But before that, let’s step back big picture. If you can share your journey, your career journey, and what led you to what you’re doing today? That’ll be a good segue.
Yeah, absolutely. So I actually, after graduating from Carnegie Mellon, stumbled into sales. Honestly, I was with an event tech company called Cvent. I started off my career as an SDR, and really captured the fundamentals of selling from there. So. Good foundation of, you know, how to use tech systems. And at that time, it was around 2012, we were on Cisco IP phones and manually dialing all the leads that we got. I had the good fortune of actually working with the European market. So that gave me quite a bit of exposure to selling internationally. And, you know, from there, I progressed in my career to becoming an account executive at sea. The event saw a transition for a private company to go public, like as well. So that was a very interesting like change to see. And then went to an HR tech company called Belong, where I was an account executive. The mid-market segment pivoted to being an account manager and dealing with existing customers, so dealing with the customer success and delivery side of the house. I’ll talk a little bit more about that later, because I think it’s made me like a better sales leader, having some experience in customer success, but that my experience at belong actually really made me understand and pivot from an employee mindset to an operator mindset and an owner mindset, to have that ownership of being in an organization, and, you know, having broader idea of, okay, what can we do to help the company, like do better, rather than like the team or like myself do better only. And I really spotcraft actually was a natural next step, because, you know, I bumped into some alumni of Carnegie Mellon, who also founded, was the founder of, like, Spot trap. And it was at an alumni reunion here, and they happened to be looking at for a sales leader. And I was like, I was ready for the next step of moving into some sort of, like, a stretch leader capacity. Because I was just 29 at the time when they offered me to be a VP of sales at Spot Draft. So went through the journey of two years of imposter syndrome, like thinking, Can I even do this? And being a stretch VP, what Jason Lemkin calls a stretch VP, at least, and then really understanding, like, how to properly build a sales team, enable collaboration, and really create a winning culture.
Yeah, very amazing journey, and interesting and impressive journey of just over a decade or so, right? So I have quite a few questions that we need to unpack here. So first off, at Cvent, you started off as SDR, and then what did the team or the management fee knew that they said, Hey, Akshay is not just an SDR, but he can be an account executive.
Yeah, that’s actually a great question. I moved from being an SDR to an account executive in about a year and three months, and what, what really like helped me stand out is the fact that I would always ask, what is it that I can do more to showcase value, like to the team, to like the department, and I would go out of my way to, you know, help and mentor like other like folks in the team too, and sit and actually shadow and learn from Account Executives ahead of time so that I could transition easier into the role. So a lot of times, I would ask the account executive that I was tagged to, can I actually do this demo? Can I take care of this low-stakes deal that you’re running and help you close it? But I don’t want the credit for it. I don’t want like the revenue for it, or the dollar attainment for it, because, anyway, my like, my targets weren’t associated with that. But that wasn’t the point. Was it about right? Like, how do I prove myself by taking initiative and showing ownership, and that actually gave visibility to like managers to say that, hey, this person that is ready, and he’s ready ahead of time, that we won’t need to invest a lot of like time and effort to move them into any sort of capacity that we have on the account executive side.
Amazing.
I mean, what you highlighted are two things, right? One is, yes, yeah. First of all, you need to do your job well, which is the SDR job, but that’s one, or that’s point five. The first key point over there is that you actually were mentoring other SDRs. You’re helping out others. So that’s point number one. Point number two is that you actually reached out to account executives, shadowed them, and asked, Hey, how can I help while I learn in parallel? Right? You are accelerating your learning curve even before you took on a formal role.
That’s exactly right. Yeah,
yeah. So curious. I mean, clearly that didn’t happen. Those traits didn’t take shape at sea event, you might have seen these traits even early on, before you started your formal career. So share that insight. I mean, what led you to actually do those things?
Yeah, I mean, it’s a little bit of the peers, or the folks that I surrounded myself with in college, they unlocked like this side of me, which made me realize that it’s okay to go ahead and ask others like culturally, you know, we as Indians are not like as outspoken or not like as direct with asking for help or mentorship or guidance, and the privilege of having an international education being in the US helped it. Expose me to people who are a lot more out there, a lot more direct with like their asks, and also embed this understanding in you that there’s nothing wrong in asking, and it the worst that’s going to happen is a person says, No. So that’s where there was a little bit of the spark of, oh, you know what? There are people who are out there who are happy to help and happy to give you guidance and happy to support you, yeah, as long as you know that’s an amazing point that you’re highlighting there. Akshay, the reason why I’m saying, even from my own personal experience, I don’t know if it’s an Indian cultural thing or broadly, but even asking for help is seen as taboo. That’s one.
There’s also an internal narrative that goes on in our minds, which is, Hey, am I being weak and coming across as weak when I go out and ask for help? But clearly you didn’t anchor in those, or you didn’t seem to have those.
I did before college, in college, there was a pivot in my head that allowed me to do that. And you know, the peers that I surrounded myself with definitely have to unlock that. I totally relate to what you’re saying, which I it’s about the perceived weakness. That’s one thing. The second thing is also don’t want to inconvenience the other person. Is another feeling that we typically get, and again, we don’t. I don’t know if it’s a cultural thing, but it’s something that we’re raised with, or I definitely have the feelings that I don’t want to inconvenience the other person, you know, by asking them for help.
I guess, yeah. And the other piece, you’re so spot on, right, inconvenience or affecting others, or, Hey, maybe I’m taking too much of the time or energy. The other angle is hearing a no. What if they say no, and am I ready for it? Those are all the symptoms of imposter syndrome. There are so many things that can go in here, but by the way, so this is not a psychology lecture or a discussion. So let’s pivot back to your amazing career growth, going back to cven. So you made that transition to an account executive. That’s great. And then you joined belong, right? And you highlighted something, which is that you are not just in sales. I think. Did you take on a formal Customer Success role, or was it in addition informally?
No, I was in sales first entirely, and then I moved formally to an account manager role and dealing with enterprise account managers, enterprise accounts, and these were the likes of Goldman, Sachs, Walmart Labs, Flipkart, and I would be working with the executives of those organizations, helping them realize value from like the solutions that belong was providing and identifying opportunities for expansion within that as well. It’s at that time that I really unlocked, like, the essence of, okay, these are all the things that you can do from an expectation setting, like from a sales angle, and how that translates into what we need to deliver on the delivery side. So the over expected, you know, the overselling, or the incorrect expectation setting that you do on the sales side, getting knowledge of everything that can go wrong on the delivery side actually helped me become like a better salesperson, and that actually translated into a one of the best partnerships that I’ve seen between customer success and sales that I have currently here at spotcraft.
Yeah, nice. No, you’re so spot on, right? So many times I’ve seen Account Executives because they’re quote, unquote, coin operated, and they need to hit the target, or OT, and the commissions and all that, they just operate in hey, I need to close this deal and move on to the next one. Versus where you have shifted in your thought process and mindset is just Yes, I need to hit my targets, incentives, and all those things, good. But going back to the customer value, that’s where the transition from sales and closing a deal to Hey, from a delivery point of view, if it’s customer success or whatever organization that’s taking part in the onboarding part, are they doing their bit to ramp my new customer?
Well, yeah, there are three things that have happened as a result of this Vijay that I can share with you. One is that I started to think a lot more about long-term relationships that I built on the sales side. So there have been instances where I have upfront told prospects that, hey, we are not a right fit for you. And here are these other companies that like might suit your needs a lot better. They’ve come back to me a couple of years later and said, hey, now we’re ready for spot draft. And you know, I want to work like with you, because I was able to build that trust with them. The second thing that’s happened is that, you know, when we do work with customers, and we’re actually able to set the right expectations and create a lot of value for them, they become repeat customers again and again. So at this stage, spending six years at spotraft, I can confidently tell you that every month I get a WhatsApp message, LinkedIn, or an email saying. That, hey, I’ve just moved. I’d like to check a spot draft out. Or, you know, I’ve, you know, I’m coming into a new company, you know, I’d like to check out spot draft at this point of time as well. So there’s that network effect of like value that gets created as well. What you’re emphasizing and pointing out here, especially in mid market to enterprise sales cycle. I mean, small business, plg motion is an entirely different ball game, right? But mid-market to sales, it’s all about relationships.
If you care about that account and customer and ensuring that you are going to make them successful, it’ll come back in so many ways, as you said, right? When they move, they’re going to bring you along. Or if you told them that, hey, we’re not the right fit, you were talking and thinking in service of that customer or icon, or not even the customer, it’s that person and the organization
that’s exactly right. And the third thing, Vijay, that’s happened as a result of this is that I’ve able to embed or design a sales process that mimics what it’s like for the prospect and experience when they do come on board as a customer. So the responsiveness, the agility, the way that we actually, you know, help them navigate, like the evaluation process. It gives them confidence that this is what they can expect, should they come on board as a customer as well? So those are the three things that actually, you know, I took away, really, like, from my experience in being in customer success and learning delivery.
Yeah, yeah. That’s leading me to actually two or even three questions. Let’s, I’m trying to see which one to pick. First. I’ll list out the three questions, and then maybe we can tie in. I’ll let you figure out the narrative on how you want to do it. One is when you’re thinking, first of all, there needs to be a personal transformation within yourself. How do you elevate others? That’s one. So do you have any rituals on a daily, weekly basis that you do that that’s one second is around you? Doing it as a person is one thing. But how do you build a system that the team can take on and do it on a repeatable basis? The third, all these are not even connected, by the way, all these questions. The third is that you, as a sales leader, have to partner with marketing. And how do you do that? So I’ll let you figure out the sequence, and then we can, and my job is to make sure that you’re extracting from your memory all these stories, yeah.
Yeah, yeah, absolutely. I’m happy to take like the questions in the sequence that you shared. So if you want to repeat like the first question again, then we can dive into the part over there. Yeah.
So the first question is, when you need to elevate others, be it your employees, colleagues, or even customers, you need to have a ritual. I mean, you’re first of all, you cannot be reacting. So do you have any set of rituals on a daily or weekly basis that you do?
Yeah. So I think one of the most important things, and I tell people in my team who are actually moving into manager roles, is that the one thing in order to be really successful as a manager is to take joy in other people’s success. Like true joy. Truly be happy about like other people’s success as well. And it’s a lot harder to do that than people think, because you are naturally very competitive, right, as a salesperson, as an individual contributor. I read somewhere that, you know, a selfish individual contributor is a great individual contributor, but a selfish manager is a terrible manager. So that is very true. So the first thing that you need to do is, like, really celebrate, like, micro achievements as well. So on a weekly basis, if you ask, what is it that I do to kind of turn me into a we is Look at, look at ways in which we can increase learning in the team, and celebrate like micro achievements.
So we have, for example, something called outbound Greatest Hits. This as an example, which is a playlist of sorts, not a playlist, but like, it’s an email chain of all the best emails that SDRs AES have sent that have elicited responses, and those are sent to an outbound credits like email thread as sort of like a micro win. So people know that, okay, this is a great email, and we can all learn from it, but at the end of the quarter, what we do is that the person who’s been shouted out the most gets like a specific like shout out or a certificate, or some sort of reward or recognition for being featured the most on like that outbound sets. So that’s just one example there, but there are a bunch of these micro achievements that, when you elevate people consistently, like and highlight what’s good like in the things that they do. It creates a winning culture for everyone. It makes everyone. Start to celebrate like each other’s wins, like a lot more. So if you ask me what the ritual is, it’s like a consistent ritual. It’s not like a weekly thing. It’s a it’s almost like a daily thing that I do, where it starts from something as small as an email, but it goes to something as big as a closed one.
Yeah, yeah, totally. I think you also covered a bit about the second part, but I would like to go further right, which is you doing it on your own? Is one thing. But how do you build a system that a team can do, and no matter if there’s a new employee or there’s a turnover, right? How did you build that system?
So I think the reinforcement of values is very important. The company values often overlap with your own personal values. And when you do, ensure that you have that like right from the time of onboarding to the time of when you are doing performance reviews, regular check-ins or quarterly reviews with the folks in your team that are there. You index on two things: one is value, and the other is performance. So you can have someone who’s a great performer, but if they’re low on value, they’re not; they’re likely going to bring the team down. But if a person is high on value and like media, mid on performance, you want to invest in them, like to kind of coach them, enable them, make them better. Now, coming to your point, how do you make that system scalable? You identify cultural carriers, you identify like people in the organization who really, truly embody like those values. And you know with confidence that even when like newer folks come into the team and say, for example, we’ve grown our team from zero to 55 plus folks here at spot draft, I can confidently tell you that there are the marriage managers in this company are very tightly aligned with the values and like the way that we operate, so much so that I don’t need to be a part of like their teams or check in with each and every person directly, but I’m confident that like the values or like the system or like the way that we operate is trickling down like to all the individuals on the team, very good. So that’s good. You. We covered the first two questions.
The third question was around how to partner with marketing to elevate not just within but also your customers and the market. Absolutely. So there’s a lot to actually cover within the sales and marketing collaboration that’s there. It’s becoming tighter and tighter, even today, like the need to actually have great collaboration between marketing and sales, so much so that when you have, say, conversations around like attribution, lead source, motion, if you don’t have that collaboration with the marketing team, you’re not going to be able to go to market. Honestly, you’re not going to create value. Like the feedback that the sales team hears on the ground has to be translated into our positioning, how we talk about things, how we actually, you know, make sure that content is out and downloadables are put in over there. So any sort of, any sort of feedback that we get in the market, and like how the market continuously evolves. That has to be a almost an orchestration layer from like sales to marketing, but in the reverse way the marketing to sales orchestration on Okay, these are all the folks that have actually spoken to us or interacted with us, engaged with us at events, downloaded content, visit our website and getting all the necessary context into a smooth orchestration, conveyor belt method to in order to like action and capture like the value from those conversations, so that sales to marketing collaboration extends now a little bit beyond that. Hey, marketing is doing its own thing, and, you know, they have, like, a bunch of engagements, but like the, if you’re not talking to sales, like, you’re not going to be able to go to market together.
So, yeah, yeah, fair enough. Wow, we unpacked so much just in your first two companies over here. Just Cvent and belong. We have not even touched the spot draft, where you add right now. So you mentioned something that’s interesting, where you actually learned about this role at your alumni reunion. So things just panned out, which is that they were looking for a sales leader, and you are looking for the next challenge. So how did you go about building the sales organization at Spot Draft?
Yeah, it was actually an interesting time to join spot draft, because it’s, it was Jan 2020, so just before the pandemic began, not a great time for a sales leader, honestly, to join a B to B SAS company and but the initial momentum, the initial focus, was, like, very clear, yeah, we wanted to actually speak to a ton of general counsels, head of legal operations, to understand what is the MVP like that we need to be creating in the first place. And we spend like the first two to three months interviewing and talking to and researching and just learning from the market as to what is valuable or what, like these personas that we want to sell, to consider. To be highly valuable from an efficiency perspective. And then we spent the next few months essentially talking to a lot of people, go to market. And that was when the pandemic was like on. So it was a little scary at times too, because, you know, you’re six months in, you know, in your new gig as a sales leader, if it wasn’t for the patience and trust that my CEO actually put in me, you know, he could have easily been like, No, we’re not. You haven’t shown value yet, so we need to part ways. But it’s about understanding that, like, Hey, we’re we’ve set a good foundation, and we’re starting to see some initial traction as well. Let’s give it a little bit more time, especially when companies were all thinking about business continuity, they were not thinking of buying your software or similar solutions.
Yeah. So, actually, if I can interrupt there, Akshay, for the benefit of the listeners, a quick one-liner on what spot draft does and who your ICPs are.
Absolutely, so Spot Draft is a Contract Lifecycle Management solution. We work with companies like Airbnb, Panasonic, and Strava to help them streamline their contracting processes. So think of it this way. Every company in the world needs contracts to do business. We make the process of creating contracts, managing contracts, and executing contracts easier, faster, and better. That’s it.
That’s good. That’s good. Context. So COVID, and then
Clearly, the whole, I mean, the whole business world, everyone, even the personal world, has been completely shaken, which means you are struggling to build a pipeline, or maybe I just hypothetically or paraphrase that on my own, but that’s what I understood based on what you said, pipeline building was a challenge. Yeah, yeah, absolutely. So the learning approach that we took in the beginning did help us, like eventually, because we did have a lot of network that was created, but it was about converting that network that really mattered about five months, six months into engagement, that’s there.
Yeah, and did Spot Craft have? Were you already bringing in revenue at that point in time, because you mentioned MVP?
Yeah, so, so interesting story. Spot draft actually started off in 2017 as a contract company, and we were helping large financial services organizations actually review contracts using AI against their playbook of guidelines of their standard terms, and flagging out deviations and contracts, so a little ahead of its time. And it was very interesting, because those large financial service organizations would say, for example, get 200 NDAs per month, and they would take two hours per NDA to review, and we cut that time down to 15 minutes. So if you think about the efficiency gains, it’s massive. The problem is that at that point in time, and with the state of AI, we needed a lot of training data, 1000s of different types of contracts to annotate manually, and it would take us, like, maybe three to six months just to onboard or implement a customer. And that’s as a startup, you don’t have that kind of runway to, you know, invest three to six months in implementing like one customer. So in about 2019, we made a pivot to workflows, or Contract Lifecycle Management. And mid 2019 is when we started going to market with the Contract Lifecycle Management solution that’s there. So, funnily enough, now with LMS and like with the progression of how AI is, we brought back a lot of the work that we did in 2017 to 2019, and use that to superpower the AI that we provide to our customers today. Very good.
Yeah.
So that understands the pivot till 17 versus 2019, or even early 2020, and then COVID hit the whole world. Yeah. And what were the struggles like? What were you as a sales leader struggling with?
Yeah, I don’t think I’ve read the words business continuity more like in my life than in those three to four months between March and about June, July, and it was like, to me, it was like we were having a lot of interesting conversations. A lot of people were like, more ready to jump on virtual calls compared to before. I would say that the pandemic actually accelerated the adoption of things like Contract Lifecycle Management Solutions, because you can roll your chair over to the Legal team’s desk and say, hey, can you help me with this contract? You’re forced to use systems like spot draft could to collaborate with your legal teams on contracts. So in a sense, people started to realize that, and in order to then ensure business continuity, they needed to have systems in place that enable that collaboration. So we started to see a lot of momentum build up with early customers in India, then in Singapore, and in the US, which were the first markets that we entered. Today, about 60% of our businesses in the US, 25% of our businesses in APAC, and 15% is. Across the mayor, but yeah, at that point in time, when we were first going to market, it was purely outbound. We used a little bit of our networks to get, like, the early customers over there, but it was mainly the outbound effort that got those first few customers on board. Then what we really focused on was the experience that we provided. So what we did was create a lot of shared Slack channels where, like the co-founders and I, we would be on the Slack channels, and everyone was supported. So the initial traction or growth that we got in the US market was word of mouth.
Virality, in the context of mid-market enterprise, is rare, by the way,
So expand. I know I interrupted, but what you said just really caught my attention there. It’s customer love at the end of the day. So it’s the experience that you provide to them that enables them to go to their communities, you know, their groups and associations that they’re part of. And whenever there’s chatter about, hey, I’m looking for a Contract Lifecycle Management solution, we would organically be mentioned
in those groups, in those communities. And that’s what created a little bit of a Rolling Stone effect, where people would start to reach out to us, or consider us to be a part of the RFPs, or consider us like as a viable solution that’s out there. And one of the most interesting wins that we had was, you know, this really high growth, like tech company in the US that that we actually won their business because we were super responsive to them, so much so that, you know, when they asked for a customer reference, we were able to provide that reference to them in three hours, and we got through the evaluation process the quickest. They told us that, hey, you would need to wait for about a week and a half, two weeks, because we are completing the rest of the evaluations that are there, but you’ve completed all steps already, and I do feel that at that point of time that really worked in our favor, because we were able to show that we want to partner with you in this journey, and we are really.
Agileies, very cool. That’s actually a good segue into our next segment, which is a go-to-market success story and a go-to-market failure slash pivot story. So I’ll let you choose what you want to start off with, Akshay, but I would love for you to share that with our listeners.
Yeah, one is, one is this story that we spoke about, which is a high growth like tech company in the US, which I’m particularly proud of because of the way that we hustled, and we actually made sure that we were super responsive. It gives them a sense of what the customer success experience would be like as well. But another one where we had to be really scrappy was a FinTech company that we got on board, like from India, where, while we were going through the evaluation process, we were able to cultivate like this champion within the organization that would tell would end up telling us that, hey, we share a common investor with a competitor of yours, but we also shared a common investor with this company too. And the champion told me that the common, the common investor, is actually sending us a note saying that, hey, you should be looking at the competitor.
So I had to go and tell, like my CEO, that, hey, maybe we should also, you know, chat with the investor that we have to put in a word, to put in a word, like for us, you know, because, you know, we need to be scrappy. We need to kind of help them, you know, help the co-founders, like, establish credibility with them, and let them know that there is someone that they can reach out to for any sort of help that they need in, like, the usage of a platform generally. And they can, they have a direct line to say, our executive team here at Spot Draft as well. So it was that scrappiness that actually did tip the scales in our favor. And the reason why I like to cite that is that my CEO at the time was very hesitant to do that. He was like, you know, we know it doesn’t feel right, you know, we should just kind of continue doing things this way. And took me a bit to convince him to say that, hey, you know, this is what happens. We.
Need to do this because, like, it is going to help us, and you know, and I know that we’re going to be providing a ton of value to them, and that’s what matters, we are able to solve for the use case, really.
Well, yeah, yeah. I love the fact that, even though you saw resistance from the co-founders, I think going back to your earlier core value that you mentioned, which is elevating others. So if you think about elevating your customers, no matter what the situation is, even if it’s bleak for us, but if you think on behalf of them, it’ll just nudge you to take that extra action. Yeah, absolutely excellent.
And that organization’s been a customer of ours for that for five plus years now. So excellent.
Wow. So the second part, which is a go-to-market pivot story, if you can share that as well, that’ll be good. Yeah,
I alluded to this in the beginning earlier, but I’ll expand on it a little bit. There was, there was a there was a prospect that we spoke to at the time that we thought that, you know what, like, the use case kind of fits quite well. And you know, we should bring this like customer on board. And you know, when the customer came on board, they had a, like, differing idea of a use of AI, and this is back in 2020, and like, what the expectations that they had were a lot different from what we could offer. So early into the engagement itself, we kind of told them that, hey, this is not something that we are able to do here. Here’s something that we can do instead. They were clear that, hey, that didn’t really work for them. So we bought a base, like, No, no harm, no foul. And I actually pointed them to two to three different solutions that might help with what they were imagining, like or what they were visually expecting, like the use of AI to be with their system. So I think that was appreciated, because fast forward just last year, this conversation happened in 2020, and in 2024
No, sorry, yeah, 2024, they actually became a customer of spot draft, so about four years later, like that evening. But that was definitely a good learning experience for us as well, because it was early days of like understanding AI and what we mean by AI, what the customer thinks AI means, and it shaped a lot of how we articulate like AI, and what, how we articulate the expectations setting around AI too. So that was a great learning experience, actually.
Let’s double-click. You bring up a very important point here, actually, which is, nowadays, when it comes to positioning and messaging, everyone says, AI-assisted, AI enabled, AI powered whatever. It’s a cliche. It’s almost like you have to have some AI buzzword in there, but it’s more turning out into a buzzword. I want to double-click into this in terms of how you worked with marketing, because you need to scale this and even the product in how spot graphs should talk about and come across in the world of AI.
Yeah, it’s a little bit more nuanced when it comes to legal as well, because of the semantic and syntactic context of legal. Yeah. So you know, something as small as the governing law should be, versus the governing law can change the meaning of the entire sentence together and change how, like, AI extracts that, like, understanding. So that’s one part of it. But the other thing is that lawyers, or in-house, like legal professionals, they’re also very disciplined when it comes to reading and the attention to detail being, like, very high. So the expectation, like from Ai also understandably becomes a little higher. Now, how do you reset that expectation? You reset that expectation by talking about, you know, you need to treat AI as you treat any human being. If you take months to onboard a human being, you need to invest three months of time to make the AI provide meaningful results to you as well. And that’s the world that we are getting into, where we. Yes, there’s some out-of-the-box value that you get, like, from AI, but when it comes to a lot more of the nuanced, meaningful AI results, you need to invest the time to make it good. So that’s the positioning that we work with marketing on. We need to, kind of like help, and almost, in a sense, do some category building or awareness building of, hey, this is the world of AI that we live in today. It’s great out of the box; you get a lot of positive results straight up. So the time to value is immediate. But if you want prolonged value and you want sustained value, you need to invest the time to make it valuable for you and your team.
Very cool. I’m actually on your website, and something that really stood out for me, Akshay, is the onboarding process that’s actually listed out on the homepage. It’s in the fourth. Or the fifth section, the blade on the homepage, which is uncommon, and I sense, based on what you just shared, you have a role to play in that. I don’t know. Is that a fair assumption?
Yeah, absolutely. It is one of our differentiators, and Vijaya, that you brought that up. So there are two places where CLMs fail. One is implementation, the other is adoption. And when it comes to the implementation side of it, we need to be very clear about, Hey, these are all the things that we need from you in order to kind of set up, like the spot draft platform, configure it to your organization’s needs. But a lot of the heavy lifting is going to be done by our team, and making sure that you’re getting the value for it. A lot of times, in-house legal teams don’t get the necessary internal resources to help some spot off, because it’s the never-ending cost center versus revenue center debate that all internal teams have. How much are you trying to position and so sorry. So, who is your ICP or buying champion? Yes, in this case, so they’re the general counsel’s head of legal operations, or generally, anyone in legal operations, rev ops, sales leaders, and procurement leaders. They form like the core buying committee, but the people driving the evaluations are typically the head of legal operations or the general counsel.
Understood, yeah, and then you’re talking about a very important point when I interrupted you with that question, which is typically, again, it’s a cost center versus a revenue generator, that discussion always happens. So how did you address that? Yeah, as a brand said company.
So the thing is that when people, even in-house legal professionals, you try to talk about like, we help you close contracts faster, right? In that sense, we’re giving time back to, like, sales teams to close more contracts. And you can use that as a business case justification of revenue coming into the company at a faster rate, at a bigger rate, at a better rate because of a better contracting experience that’s there. That’s still an uphill battle. I feel like there’s still a lot of time for us to get to a stage in which we can convince people that, okay, legal is the bottom of the funnel, and legal is helping us to close contracts faster, thereby increasing revenue, and preventing revenue leakages. So making sure that you get reminders on contract expiration, so you’re not auto-renewing with a vendor that you didn’t want to work with in the next year. So, preventing revenue leakages and then quantifying that into, like the revenue center debate too, but that’s still like an uphill battle, like you can quantify, like the ROI, that’s fine. But when it comes to, like, legal teams, it’s typically about, okay, how do I kind of show visibility on all the work that I’m doing first? That’s the first thing. Because in our ICP, and let’s talk a little bit about our ICP, we sell a lot of mid market upper mid-market companies primarily.
And when you’re talking about mid-market teams, you’ll usually have very lean legal teams, like, maybe from one to about, say, 1011, like legal teams. So it’s a lonely function, right? And when you talk to like, when you talk to legal teams, and you ask them, hey, what makes a good year versus a great year in legal, they often don’t have KPIs because it’s hard to set KPIs against. An MSA, which is five pages long, can take about two hours, or it can take 20, depending on how complex it is. So it becomes hard to have turnaround time as a metric, and when you’re looking to track metrics, even at that point in time, you have bad data, because when do requests come in? How do requests come in? Should you be sitting and tracking that, or should it be closing business? So they often don’t have time, and they don’t have good data. That’s where systems like spot traffic come in, plug into, like their day-to-day work, you know, minimize as much change management as possible, increase adoption, and give them the data that they need, the visibility that they need to showcase to the executive team that, like this is where we stand today, understood.
So in a way, I mean, this is a mantra for any product or a go-to-market. Right at the end of the day you need to make your buyers and users heroes
at the end of the day. That’s what it’s all about.
More very simple, easier said than done, for sure, but what I’m hearing in the way you articulated that actually is around, how can you make the quote, unquote, boring and mundane teams like legal show up as heroes. So that’s what I heard and took away when you were talking about the transformation: how quickly they can turn around, which means they can increase the speed of their business.
Absolutely no one went to law school to do NDA. Yes, and employment agreements. So, to your point, you’re absolutely right. Like our job is to take away that work that you didn’t go to law school to do. Yeah, so
right, the repeatable, high-frequency, like work that can be made self-serve. We make that self-serve so that lawyers can spend more time on the strategic, higher-leverage work that they want that is interesting for the company to do as well, and that is a lot more value adding, and it makes them look like heroes. Yeah.
Yeah. Very cool. All right. I know we are coming up against time over here last few minutes, so I have a couple of more questions for you, actually. One is, what resources do you lean on to up your game, or even for your own mental well-being? It can be across the board, right? So what resources, communities, people, podcasts, books?
Yeah, if you can share that, yeah. So I am a voracious consumer of podcasts, and specifically the GTM podcast. So this podcast is my new favorite of mine, actually, as of a month or two months ago, I’ve been hearing a ton of episodes of yours. Vijay, I do listen to the 30 minutes to presidents club podcast. Jason nuggets, Sasta podcast, Pavilions podcast as well. So a bunch of those podcasts are like, a primary way for me to on the go, like, just consume, like, knowledge is one. The second thing, like, is really being on the ground with customer conversations. That’s one big way I learned. I think the biggest resource and biggest advantage that we have is, like GTM leaders, is our ability to kind of be on the ground and hear what’s happening like in the market. I also really enjoy connecting with peers and other startup-like founders and operators and learning about what they’re building. So one of the fun things that I like to do is that we have spot draft alumni who are building their own businesses today. So just learning, and you know, if I can add any value, like to their businesses, I try to do that as well. People say that spot draft is a pretty startup-friendly place, because we’ve been through the journey where people took a chance on us. So we like to take a chance with POCs, with other startups too. So it went through the network of like-minded individuals, peers. Like learning directly from them is another way in which,, like I really learned. So again, podcasts, customer conversations, and the network
Very cool. And thank you for that unsolicited mention that you’re going to be a voracious listener to this podcast as well. So I’m honored by that trend. A new trend that I’m sensing and seeing is being part of communities, especially in WhatsApp groups, like closed WhatsApp groups, where you need to be filtered, and people need to let you in, right? So, are you part of any WhatsApp groups? Are they not real?
No, not yet. No. I do get invited to a couple of these community events that happen for like, B2B GTM leaders. So I do tend to attend them, like from time to time. But this WhatsApp groups idea is something that I’ve been taking note of as well. Because, just as in-house legal teams are also lean and like they’re lonely, I feel like a, b2b, GTM leaders are also a lonely function. Yes, in terms of who they can learn from, they can learn from peers and other GTM leaders. So I do see a lot of value in that, interesting.
Yeah, point noted. So final question for you, Akshay, if you were to turn back clock and go back to day one of your go to market journey, what advice would you give to the younger Oh, boy, you’re already young, by the way, not say that you’re old, but even if you go back 10 years,
yeah, no, it’s a spend about 14 years in B to B SAS sales and customer success roles. If I had to, if I had to go back and tell myself something, I’d say maybe invest in Apple stock. No joking.
Never heard that, which definitely brings a lot of laughter to the listeners.
Though I would, I would go and tell myself that, Hey, start to learn a little bit more about other functions earlier. Because I think early in my career, while I was taking a lot of initiative, like within the same sort of growth path that was designated in sales. So from SDR, you were supposed to be going into an executive role. I there was a lot of scope for me to learn more about marketing, customer success, Product Engineering, and that is something that I would definitely tell myself, like early in my career, being like, Hey, why would you show the same initiative to learn about how companies holistically run themselves. That knowledge actually came to me, like when I was in the second company. Good.
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.
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.
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.
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.
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 theinside 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 yougrew 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:
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.
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.
