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.

Connect with Vijay Damojipurapu on LinkedIn

Connect with Akshay Doshi on LinkedIn

Listen To The Episode:

From SDR to SVP of Sales: The Go-To-Market Thinking Behind Akshay Doshi’s Rise

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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.