Joining Productboard

Alex Kracov: So you joined Productboard as a founding AE when Productboard, I believe, was like around 30 employees. I would love for you to kind of take us back to the early days of Productboard. Why did you join? What was the company like at the time? What was kind of like that early product you were selling?

Conor Dragomanovich: Yeah, I'm thinking back now. So I moved to the Bay Area when my wife got into a medical school up here - then girlfriend. But I knew I wanted to join a very early-stage company. And that was basically the only criteria I had. It was a terrible sort of like criteria to have. I didn't think much more about it. I initially joined this company called Dealpath where I spent about a year, and it was also early stage. I was also their first AE, and I did just about everything wrong that you can possibly do. But it was still a great learning experience and a ton of fun. But at around a year marker, I knew I wanted to do something different. At the time, I was selling commercial real estate investment management, kind of like a deal platform. And so that didn't necessarily excite me. This was at a time when - PLG had been around. But this concept of it was starting to really emerge, and I got really interested in that. I knew I wanted to work for a company that this was prevalent in, and so I started to look around at those. I interviewed at companies. I actually interviewed at Lattice as one of the early AEs there. I don't know if I ever talked to you about that.

I joined Productboard because it seemed really attractive in that way. I also loved that it had this sort of European presence. I thought that might open up interesting opportunities as well at the time. And so it was very early days. I don't know. It's between 30 and 40 employees, I believe. And what really did it for me was meeting Hubert, their CEO, in one of the final couple of interviews. There's just something about that guy. He is like, it's very, very infectious. This is true of a lot of founders who just exude energy and excitement about what they're doing. And hopefully, that's true every time when you're talking to a founder. That was certainly true for Hubert. He did as much selling of his company and of his product in that interview as they sort of asked me to do in a mock environment. And that certainly sold the deal.

Alex Kracov: Very cool. Then were you sort of transitioning from Hubert doing all the sales himself to bringing in a few AEs? Was it kind of that classic transition from founder-led sales to sales-led sales, or was there already an existing sales team once you joined?

Conor Dragomanovich: There was no existing sales team. I joined alongside another founding AE at the time. Like him and I started the same day. So we joked about who got in the office first and can claim number one. But yeah, I would say it was definitely transitioning from founder-led. There's definitely a product-led element and a big one. I also joke and say that it was Winston-led. He was a product marketer working there at the time and was like one of the most talented people I ever worked with. He was doing a lot of that.

Alex Kracov: It sounds like you followed that classic, like the Jason Lemkin advice of hire two AEs at once so they can compete against each other and also get a sense of what style AE works, which I think is just amazing advice. Because I've developed it in my own sales team at Dock. It's like yes, you need that to pressure test, okay, the different styles and approaches.

Conor Dragomanovich: Definitely. I've done my fair bit of advising, and I get asked that question a lot. Because it's usually where I do it. It was with early-stage companies. And I always say hire two for those reasons that you mentioned. You can learn from one another. You can run experiments. You can AB test. You compete. I was the best man at this guy's wedding many years down the road. So there can be other benefits as well, maybe. So that's great.

Inside Productboard's PLG Motion

Alex Kracov: And so you mentioned Productboard had this awesome PLG motion. Can you talk a little bit about that? Who was signing up to use the product? Are they just putting in their credit card and then you were sort of upselling them to an enterprise package, or were you just taking people from free to paid? What did it look like in those early days?

Conor Dragomanovich: Yeah, it was taken from free to paid. But there was, in many cases, a sort of credit card option that you could do. That developed as all these things do overtime. I think one of the things that made Productboard so compelling, especially in the early days, was that it just made it very incredibly easy to get going. The early value prop revolved around allowing a product manager or a team to get in and set up a quick integration with where they received customer feedback, like an intercom. So they could just get in and immediately start seeing that value. And so that zero-to-one chasm happened really quickly. And for us, it then became this very, at least at the time, easy opportunity to come in and say all of these free trials, who were the roles, the users, what type of usage. And it became this great opportunity to select who we wanted to meet with as part of that, especially in the early days.

Alex Kracov: I find the product persona, in general, both product design engineering, it works so well for product-led growth. Because I think it's the type of person who just likes to get in there, play around with the product, and they also just know how to use product. They know how to give feedback. They really think critically about how they use that. Whereas some other personas, it can be a lot harder. Actually, sales with Dock, it can be a little bit harder because sales folks just want to get to the next deal. They'll mess around a little bit. But oftentimes, it's just in the purpose of closing something. Then product people - I don't know. There's a different mentality about them which must be really nice for PLG.

Conor Dragomanovich: I think that's exactly right. There was sort of this baked-in deep empathy that our customers already had for the process we were going through. It made conversations really easy when a product leader wanted to know where something was on the roadmap, and we'd say or joke that our own product team would kill us if we gave away too much or made promises. That always got a laugh. Then I think there was also this concept of appreciation for even if we weren't maybe shipping things at the speed that anyone would like - we all want things to come faster - there was this really close focus on creating a delightful user experience that they just couldn't help but sort of admire. Or at least, that's what we often heard. And I think that helped a lot.

Alex Kracov: Yeah, really interesting. Okay. So the end user, the product manager signing up for the product. They want to organize product feedback. They're doing some roadmapping in there. What did the sales sort of look like from there? Are you just grabbing a bunch of user seats to try and get all the PMs on board? Are you bringing in design and engineering? How did you sort of navigate, I guess, all the different personas in the EPD organization?

Conor Dragomanovich: Yeah, we spent so much time on this as we sort of went back and forth as to how we think about expanding at the ICP, and what makes sense in terms of who we target as we multithread and try to sort of just capture more share. This definitely became a big part of it. The first and foremost was just get as many folks within product using this as possible. But the design team was sort of a natural extension of that. And to your point about EPD, there really wasn't as much value if we didn't get buy-in from the engineering team. Because at the end of the day, this thing had to connect to a system like Jira. Because you can capture all the user feedback you want. But if you're not then sending this out for it to turn into stories and epics and development to actually take place, it loses substance very quickly. So it did become sort of a cross-functional effort in that way as it relates to the stakeholders that we tried to engage with. We spent a lot of time in the early days thinking about in what order and how do we think about where each person sits as far as their influence in getting something like this spread across the org.

Alex Kracov: Yeah, would you try and just kind of like bear hug the entire EPD org, or is it sort of like land and expand of just start with the PM world and then, naturally, it would grow into design and EPD? How did you sort of navigate that motion? Because I'm dealing with very similar stuff myself right now.

Conor Dragomanovich: Yeah, I think the latter, more so than ever. There were certainly circumstances and even some where we started with design. But more often than not, it was a land and expand to get really deeply integrated with the product org. Because at the end of the day, so much of the usage, like the day in, day out usage, was going to come from them. That being said, if we sort of ignored or did not do our diligence in discovery and in building relationships with the D and EPD, as well as the E frankly for that matter, we were going to do ourselves a disservice. And if we didn't get buy-in, like when we did see some deals start to slip or fall apart, we knew that there was probably someone, an engineering leader or a CTO, that was uncomfortable with this. And so that was a really big part of just even getting in with the product team. We knew we needed to get that buy-in.

Alex Kracov: Did it feel when you first started at Productboard that you just had product-market fit immediately, and you were sort of already caught lightning in a bottle and were just sort of running with it? Or was there sort of a moment while you were there where you're like, okay, this is really working? How did you sort of think about that puzzle?

Conor Dragomanovich: Looking back now, at the time, yes. I always think the product-market fit is a tough question. I know that at the time, we felt quite confident that we had it. And given the success of those early years, I think it's fair to say we'd achieved it. So yes, there was a concept of there's so much inbound. It is "easy" to convert a lot of these deals. But I think with so many companies, we found product-market fit is an evolving organism. And when you're sort of aiming at this moving target, you have to think about what that actually means for the business and what you really want product-market fit to actually be as a definition.

Alex Kracov: Yeah, I very much agree with that. Because I think, yeah, everyone talks about product-market fit as this, like, we got it. It's like very binary. And no, it's like you have it for a moment in time. Maybe within one segment, one ICP. But then as you start to play around with your segment, try to bring bigger deals, whatever product-market fit, you might lose it in that segment. You might have it in some, not others. And you got to keep just evolving iterating both your product, your pitch, your servicing, all of that stuff. So that's what makes it fun, though.

Conor Dragomanovich: That's exactly right.

Alex Kracov: What was the biggest competition for Productboard at the time? Was it sort of like the non-competition of people who are just using spreadsheets and Google Docs, or was there a really kind of more incumbent software provider that you were going up against?

Conor Dragomanovich: There was definitely big elements of both. But I would say there was. There was a definite, there was certainly an incumbent in a company called Aha. Frankly, I probably regret not spending more time thinking about them, which might sound strange. Because they were really good. We had this great problem of so much inbound. And it can be really easy to develop this skewed perspective when people that you're speaking with are so opinionated in preferring your product. But the reality was that this competitor was bootstrapped. They were already supporting large enterprises, and they were just doing a lot of the right things. And I just became - for me, personally, I wish I paid them more attention. At the time, I felt really confident in my narrative around how I positioned it. But I think had I sort of thought more about all those things that they were doing right, as someone with at least a small degree of influencing with the company and product direction, I feel like I could have given that more merit.

Alex Kracov: And why is that? Did you feel like, I guess, that Productboard maybe got too confident in its own offering and then when you started to go up against them in bigger deals, you were sort of losing on different feature parity battles? Is that kind of what seemed to happen?

Conor Dragomanovich: Yeah, I mean, I think I'll sort of separate myself from Productboard in that feeling. I'm sure Hubert would say, probably like, we never sort of lost sight of what they were doing. And we felt pretty confident about, at least the decisions that we made in our deference to a good competitor. But for me, you fall into that trap of speaking with so many customers who create this differentiation in your own mind, of maybe thinking that you've created a much better experience, and you're more user-friendly. And we fell back on this sort of concept of, like, we're different philosophically. There are directions they're going where we won't go because we sort of think about how you do product management and what that is as a principle differently. That might be true. And I think it really helped in a lot of deals. But at the same time, there were some customer needs that I think I hustle really well. Actually, I caught up with their founding AE after I left, and it was fun to sort of trade stories.

Alex Kracov: The competition is dynamic. It's so interesting in SaaS. Because I think, to your point, one of the best ways to win is by comparing like apples versus oranges, right? It's completely different things. Like, do you want an orange? Do you want an apple? Pick which philosophy you want. But then, especially at Lattice and now at Dock, I actually love the competitive deals. At Lattice, it was, we first were going up against Reflective. Then it was going up against Culture Amp. The competition was so nice because you could learn how to beat them. You could learn what features to ship to get to feature parity with them. Then you sort of knew where their strengths, where your weaknesses are, where your strengths. It was more of a playbook and a deal. As opposed to when there's no other competition, it gets a little bit harder. It's a little bit just kind of up in the air what you're comparing yourself against. And yeah, I don't know. You want to be in those competitive evaluation cycles.

Conor Dragomanovich: I think that, yeah, I think that's really well said. I think it is also a reflection of maybe some of my early sales training, or at least how I thought about it back then, where you do a lot of deflection when you're not as comfortable leaning in and dealing with some uncomfortable conversations. And so you do create this sort of pivot that you might get really good at. And it's probably helpful, but you ended up not learning as much a lot of the time. And so that's something I would have done differently.

Alex Kracov: I'd love to spend a little more time on the product-led side of things at Productboard, because I think it's super interesting. You mentioned, I think, did you have free trials, or was it freemium? How did you think about - did you timebox kind of that free account experience? How did you think about kind of those mechanisms to get them to, okay, putting your credit card or not, talk to sales or not? How do you think about that?

Conor Dragomanovich: Yeah, I thought about it a lot. I ended up eventually, I was in every - not every, but at least weekly growth meetings. Because I was so deeply interested in how the team thought about the user experience and how we sort of optimized for some of these natural lightbulb moments to get more experience from the product so that we did know who to target based on their propensity to convert. But we didn't have freemium, at least not at the time. It was all sort of a trial experience. I believe it's 14 days, 15 days. And so, if my memory serves me correctly, so yes, there was lots of crafting a sales process initially around inbound based on who was requesting trial extensions. So much came in the way of this isn't going to be enough. And so that was a bit of an exchange, as far as these tradeoffs that you make for a conversation. Let's have a conversation. Learn more about what you're trying to accomplish so that we can ultimately end that certainly by achieving your intended outcome of getting more time in the product, but also helping us sort of go through that qualification and understand whether or not this is going to be a good opportunity for us to pursue.

Alex Kracov: And so when somebody reached out and asked for a trial extension, would you force them to get on a call? Would you grant in certain circumstances if they were a good prospect? Would you do like a big sales pilot where it's like, okay, you can try it for 30 days, then you're going to upgrade at the end? How did you think about that? Because we've tried to do that at Dock and it was like - I felt like I was just moving these dates around, especially in the early days. We ended up doing more freemium. But yeah, how did you think about sandboxing that trial extension?

Conor Dragomanovich: We tried all those things. They're almost blurred in my memory as you rattle them off. Because I think we went through the stages of let's try this and let's try that. It was a lot of, like, we'll have to chat if you want to extend the trial. It's not a great user experience. But it was the way that we sort of managed to learn a lot about the customer and sort of decide. We never left those without extending it. It was not something we necessarily held hostage. But I would say that it was something at least I leaned on really heavily in lack of maybe better sales skills or other things in my tool toolkit, as far as just sort of using product access to maintain a certain level of engagement. And in some cases, it really helped. Extending that access and building trust led to some of our largest deals in the early days. But it also, I think, reflected, at least as far as my own approach went, a bit of like a lack of experience in how to navigate more complex deals in a way that maybe you didn't require a line on something like a free trial and extending it as opposed to like your other example, which we did eventually try. More like formal pilots or proof of concepts where we got really tight on success criteria and things of that nature that led to a mutually agreed outcome.

Alex Kracov: I'm curious how you thought about sort of product-qualified leads and if that was a concept that you were using at the time, like PQLs? Were you scoring up all of these different activities within the product and be like, alright, this one's ready to buy? Did you use that, or was it really just like time-based trial, and that was the main trigger?

Conor Dragomanovich: We didn't at the time that I was an IC. It wasn't so much a concept. Maybe it was, but not one I was familiar with. It's funny. I remember speaking with Alexa, who founded Pocus, before she started the company. And we talked about this. At the time, I was like, this is amazing. I think it was similar to Productboard when it first launched as far as it being a concept with regards to product-led sales that wasn't really known or known very well. And so, for us, what we did was just kind of like brute force our way into understanding it, sort of going into admin consoles and looking at what are the things that seem to give the highest signals as opposed to having this clear definition of what PQLs where in a really natural motion. We got there as a company. But in the early days and when I was selling, we didn't have those things.

I recall a really obvious or obvious in hindsight light bulb moment for us was, we saw how high conversion was when users had set up an integration with Jira, for reasons I had sort of mentioned before. There was this really critical link happening between product and engineering that had been established, and those users converted 80 plus percent into paid customers. And so, so much of our catalyzed such effort on our part to then figure out like how do we make that connection much easier and how do we help foster.

Alex Kracov: Yeah, PQLs, it's such a powerful concept. And shout out, Alexa. I love what she's doing at Pocus. But yeah, we haven't quite set up something like that at Dock. Because we're still so much in the experimentation phase and our analytics aren't robust enough to be like, alright, if they do this, they're exactly going to convert in that way. We're still just figuring out and ship trade is trying to ship as many features as possible. But I'm excited for the day where we have a very scientific PQL, where it's like, okay, this person is ready to buy. So one day. One day.

Conor Dragomanovich: Totally. Yeah, it makes a big difference. But it is a hard - it's a tough nut to crack even when you have a great platform to help you with.

Moving Productboard Upmarket

Alex Kracov: Yeah. Alright. So you eventually transitioned to more of like an enterprise AE role at Productboard. How did you think about helping Productboard move up market? Because I have found, some of these bigger companies don't always buy in the PLG way. They like to be, lead the horse to water or whatever that thing is. So how did you sort of think about that move up market for Productboard?

Conor Dragomanovich: I mean, pretty inelegantly, honestly, I was new to that. And so I think my most direct contribution was through just managing to get in and sell at those larger companies - in some cases successfully, in some cases, unsuccessfully. It's worth noting that these companies probably weren't ready to take on a full deployment with Productboard, at least in most cases at the time. They weren't ready to do these wall-to-wall deployments. But it was about getting into those conversations. And as soon as we started to do that, and when you're making this push up market, you get punched in the nose repeatedly but you're learning a ton. Those lessons are very valuable, and getting the type of feedback and understanding of how the way that they think about best practices in the world of product management might differ, but also just some of the basic brass tacks needs that they have that are table stakes for up market or for an enterprise company, that you then have to decide about what tradeoffs make the most sense if you really want to push meaningfully up market.

Alex Kracov: So it sounds like you didn't quite maybe have product-market fit in that enterprise segment when you first started, or at least maybe you had some parts of it, right? How did you think about your relationship with other stakeholders at Productboard, product team, senior leadership team, of getting that feedback back to them so that you can then go be more successful in the enterprise segment? What did that look like?

Conor Dragomanovich: So I give Hubert and the rest of the team a lot of credit, because they made themselves extraordinarily accessible to both the customers that we were trying to connect with but also to our team who was providing this feedback. So it was very much a sort of ongoing, an open dialogue around what we were hearing. And to your point, I think in some cases, it felt like, yes, we have it. And it's really just a matter of what is the right motion and how do we spend our go to market calories really efficiently. And in other cases, we felt like, oh, we need to release A, B, and C in order to really do this at scale. And so a lot of it did turn into these conversations. And I can remember many where it was like Hubert, my VP of product and I, and I will be talking about this large deal that we were very close to formalizing, but they would have asked us in things that they wanted contractually written in there in terms of the commitments we would make to developing certain functionality that provides the level of flexibility and administrative rigor that an enterprise company needs. And so I think establishing that feedback loop is really important. It goes without saying. Thankfully, that was our whole-

Alex Kracov: Good product to do it.

Conor Dragomanovich: Yeah. So that it would be silly if we didn't sort of like at least honor that.

Alex Kracov: Yeah, it's such an interesting balance as you move up market. You just don't want to be like a custom dev shop where you're at the mercy of this big company. You got to build all this stuff for them. And so it's this interesting game of, okay, we can build some things, but you got to be useful for other people too. And so that's a really interesting, delicate balance.

Conor Dragomanovich: Yeah, and one of the - I didn't mention this at the time, but I was so keen to join Productboard because that was just a world I wanted to learn more about in terms of how products get made and what this actually entails as a philosophy in building a company, which is done by so many great product leaders of the world. And so there was insight in those conversations every time. As a seller and an enterprise one, it felt like you just need to do this. And in some cases, maybe you make that trade off. But a lot of the time we didn't, because there was a very specific vision. And you have to think about more than just this one customer that's in front of you.

Alex Kracov: And was the sale for these enterprise companies generally the same of PLG, end-user product manager comes in, you capture that momentum and kind of go to the bigwigs of the company and be like, look, this is a small example of how you could use Productboard? Or, was it more of a top-down sale, you're out bounding to a CPO or somebody like that, or was it both? How did the sale change as you moved up market?

Conor Dragomanovich: There was elements of both certainly. I did find myself more having to do bottoms up than anything. And it wasn't ineffective. Thankfully, because it was a strong PLG motion, you would see these pockets of success from product departments within large enterprises. It might not have been the fastest way or the shortest distance between two points. But I would go in and work with directors and, even in some cases, VPs at large enterprises and just focus on what they were trying to accomplish. Then I'd go to the next one and then the next one. And all the while, you're out bounding. You're multithreading. You're trying to get exact access. You're trying to make tradeoffs for the things that you help these champions with in an effort to get access to senior executives. That's eventually what got us there. It was doing that work with them through which we could finally take something of substance and value in the way that we'd been proving out value with these other teams to talk about a larger type of partnership.

Alex Kracov: Would you start multithreading right away? Like you see an end user come in. Do you just start reaching out to everybody else at the company, or do you really try and leverage, okay, this end user and get them to introduce you? How did you think about that multithreading puzzle?

Conor Dragomanovich: I think early on, I did. It was sort of a natural - at least, it seemed like a natural next step for me. Like, hey, we've seen interest. At the very least, what I can do is reach out and say, hey, this is sort of what we're seeing from some members in your company. We don't have a partnership yet, but I'd love to establish that connection as we explore sort of what a product management platform can do as far as achieving certain business initiatives, things like that. And in some cases, rare cases, that was effective. What I found more often than not was that we tended to have to do more of the upfront work, and then use the relationships that we were building for connections. We had some luck with the cold multithread but much more success from doing a little bit more of the bottoms up, which I don't know is true of a lot of companies. I think others would prefer the reverse for obviously reasons.

Alex Kracov: Yeah, at Dock, I mean, we're PLG too, and we have a bunch of end users. But I think what I learned is like we sell it to sales. And so every salesperson you talk to is like, "I'm going to help you multithread." Right? They'll say that you ought to call, which is so funny, like, game respect game. But then they get distracted, things. And so I think what we have learned is we got to just start multithreading right away. You know, it's like get the end users, start reaching out, start building relationships. And yes, you should work through your champion. But there's moments where it's okay to go around them or to talk to other folks within the organization and show that. So it, I don't know, a big lesson of ours over the last couple years.

Conor Dragomanovich: Yeah. I mean, especially now, I think there was something to be said for the culture of the companies. Not culture of the companies, but sort of the nature of the way that they worked in terms of product orgs and where budget came from, and which executives were ultimately the economic buyers. But I completely agree. Sort of looking back, it's unfathomable that we wouldn't have just sort of programmatized more early on just getting that type of access and doing more just cold outreach to make executive teams aware. But we didn't do it as often, or at least we were unsuccessful in our efforts to do it.

Transitioning from AE to Manager to VP

Alex Kracov: So after a couple years, you became a sales manager, and then a director, and then eventually a VP. And you've ran a team, I think, of eventually around 30 plus people. But I'd love to start with the first step in that transition. What was it like moving from an AE to a manager? Were you sort of like a player coach role? How did you navigate that first upgrade in your career?

Conor Dragomanovich: There was a major transition for me, as you can imagine. When I was in college, I managed to serve shops. And so I had anywhere from 8 to 15 employees reporting to me - sales associates, college kids. And so there was an element of leadership that I had some exposure too, but these are very different things. So yeah, it was a transition. I was definitely a player coach. I continued to carry a bag for at least another full quarter. I think I had six AEs reporting to me at the time. I think with any young leader, you learn really quickly that it's not about stepping in at every opportunity and telling an AE what you would do in that situation. You really have to develop a leadership style of your own and a set of values that you can lean back on. Then of course, learn how to do the job. It's not just like I was a great seller, and that will make me a great manager.

Alex Kracov: If I was your AE, what would it be like working with you? Are you pre-gaming every sales call with them? Are you joining the last call of every deal? Are you listening to Gong calls, providing notes? What is it like to be an AE who works for Conor?

Conor Dragomanovich: I would say the coaching and mentoring of sales reps was always the most fulfilling part of the job. I was never the person to pretend that I had it figured out or that I knew what's best. I would say I did lean on the experience that helped me be successful in the role to give guidance. But as much as it is with helping a customer solve problems, I felt like the value of a leader is the ability to really and truly listen with the right intentions, and ask meaningful questions, and help both the AE and then yourself uncover the productive learnings and carve the right path out. So to your question, absolutely. If you ask anyone who I've ever worked with, both here and other companies, about my opinion of Gong, they're like, "That guy is a heavy user." So it was sort of my superpower. As an IC, I would devour calls to understand our customer, how they respond to the different ways we're positioning ourselves and our product.

And then as a leader, I think having the ability to run call-listening sessions, pull snippets for use in strategic discussion, it just amplified the way you can work with an AE. You understand their approach. You're seeing it from the perspective of the customer. And it's just so different from being able to listen to the way an AE is handling an objection, overhearing or trying to brute force your way into a bunch of live calls, that you will now have all of these contexts that you can reference in moment and give real-time feedback. I leaned on that a lot, especially in the early days where I didn't have as much of the other leadership skills developed. But I could just work and listen to calls and then meet and spend time with the reps to talk through what my approach might have been, understand which path they were taking, and then we can use those opportunities to sort of strategize.

Alex Kracov: How do you think about opportunity pipeline reviews? What does a good pipeline review look like? And what cadence are you doing at that ad? What does the agenda look like? What do reps expect it to bring? Can you take us into one of those reviews?

Conor Dragomanovich: Yeah, I think I probably tried different versions of these, especially as the team grew really quickly. At the end of the day, a good review should give the leader very clear visibility into the good, the bad, the ugly of their pipeline. And so, for me, it often like it was about answering the question, where are we exposed? That can mean different things. Where are we exposed in this specific deal? Where are we exposed in the context of our commit or most likely our best case, and so forth? So I would approach these - basically, I would try to keep pipeline reviews done at an individual level, and I would try to run those weekly so that when we ran a forecast call, it can be done very efficiently, especially given the size that our team grew to really quickly. And so the goal of that meeting would be to walk away with a very firm understanding of what's possible so that we can roll that up to high levels of leadership.

What I just found was a thorough pipeline review is very, very difficult to do with this large team of AES, even if you have a lot of time. And so I would try to concentrate them at an individual level. And when you would do these as a team, the expectation always was, I need to come in with, basically, having already asked myself these questions as it relates to anticipating what a leader would ask. And so we would run through these exercises at individual level, where they could look at their pipeline through my eyes and start to look for those exposure areas.

And so we did it in a pretty classic commit most likely best case standpoint. By the time we got to the true forecast pipeline review call, there should have been a lot of inspection done up front at the individual level. And when we did that and ran those calls with just one to one, it was really about seeing like where are the blockers, and how can I help? Why would this deal not close? It was a lot of looking at this from that perspective in terms of what are the things that would happen to prevent us from getting this done and then working backwards to mitigate that sort of outcome we didn't want.

Alex Kracov: When you transitioned to a director role, and then eventually to a VP role, you went from managing sales reps to managing managers. What was that transition like for you? How did that impact your your day-to-day life and your leadership style?

Conor Dragomanovich: Yeah, it's an interesting question. It was a big difference for me, and I think probably for a lot of people. It was, at least in my experience, it was about like the difference of skill development and career coaching. These were things that challenged me and that I had to think a lot about. I think by the time I was managing managers, I felt confident, at least to a degree, about my ability to be an effective-ish leader to ICs. With leaders, it felt like I was starting the process all over again. I had to do a lot of introspection in terms of what I felt my strengths and weaknesses were as a leader, what my values were, without necessarily projecting that on the managers themselves. And so I think with a lot of AES have different styles, this is true of leadership. But the stakes felt higher to me because I felt like the weight of responsibility of the success and psychological safety of the entire team. So where I think a lot of best practices were in terms of like - basically, I spent a lot of time reading lots of books and podcasts and resources. And mentorship was pretty much everything for me. Like getting a firm group of mentors who had been there and done that, probably, was what made the biggest difference in helping me feel more comfortable in the role.

Alex Kracov: Yeah, same for me. I got a marketing coach. And I think the hardest part about it, too, is like you feel so much pressure to hit your number for this entire org, but then you have the least amount of direct control that you've ever had, right? And so now you're managing through other people. And you do have to be like a leader. You have to inspire people and set the goals. Then you also have to develop some framework of accountability to hold your managers accountable, so I hold the team accountable. And so everyone sort of knows what's going on. It's a very tricky, sort of weird process. It feels very different than being a manager or just like an IC. So yeah, it was a big transition for me, too.

Conor Dragomanovich: Yeah, very true. It's like how do you increase your impact but with fewer, direct one-to-one conversations? And that can be a difficult balance to strike.

Alex Kracov: Yeah, it's weird being the big boss. In the group, you still feel like, okay, I'm the AE who started or whatever.

Conor Dragomanovich: That's for sure.

Advice for Finding Your First AE

Alex Kracov: Yeah, exactly. So you're like a founder's dream, right? You joined Productboard as the first AE and then kind of rose up through the ranks. And we're clearly very successful there. How do founders hire more Conors? What do you think founders need to look for when they're looking for their first AE hires?

Conor Dragomanovich: I think about and talk about this a lot with other founders. It can be a difficult profile to find. Because their - I don't know why a lot of people would sign up for it candidly. It's not an easy job. It carries a lot of risks, and there's not necessarily a whole lot of playbooks. I think nowadays, there's a lot more that you can find in the way of resources. But my guidance has generally to try to find that sort of Renaissance rep, which I used to refer to this term differently. But a colleague of mine referred to it this way. Have you heard this term Renaissance rep more recently?

Alex Kracov: It sounds familiar, but explain it to me.

Conor Dragomanovich: Yeah, I never really heard it used this way. But it really aligned with how I think about this role. It's somebody that you can interview to understand how comfortable they will be within the constant turbulence that is like being a founding AE in an early-stage startup. Which is to say like, how do they think about problem solving? And are they demonstrating an active mind? To what extent can they create process where there is none, and frankly a process that is probably not going to be great? It'll suck, and that's okay. You just sort of like detach. Because there's plenty of folks out there who you can hire that are very tactical and are really good at building things. But that's all they really want to do, and they will get really obsessed with what that thing is and incapable of moving on to the next problem.

And so I've always thought of it as, like, find that salesperson who's a bit of a micro operator and that they are really good. They have this sort of natural things that you would look for in a good seller but that they have this bias towards action, where you know that you can set them loose with very little oversight and that they will either come to you with problems, or they will come to you with the problems that they have solved. And it takes a lot of trust as a founder, really with anyone, any leader, to do that. But you have to try to sort of work through the process of interviewing and referencing in behavioral questions to understand if they might fit that mold.

Alex Kracov: Yeah, I think it's very well said. I always thought of it as like this very creative seller. When I think back to Seth who was the first sales rep at Lattice, he's constantly coming up with ideas to get in front of the prospect or to mold the pitch and mold our product, and then go back to the product team, and coming up with solutions to get the deal done. And it's so different than when I think of skilled AEs look like, where it's like here's your process. Go. It's the exact opposite of that. And it takes a certain creativity but also just mental capability to not get tied to anything and to constantly change and to be okay with a lot of rejection and a lot of change, which can be very hard in the early days of a startup.

Conor Dragomanovich: Yeah, absolutely.

Alex Kracov: I'm curious in this journey of Productboard. What was it like for you personally? How did you think about scaling yourself? At each of these different phases, how did you get better? Were you just reading a lot of books, mentors? How did you sort of deal with that on a day-to-day level?

Conor Dragomanovich: Yeah, I had stumblings I didn't share. I'm bad at complimenting myself or sharing compliments about myself. But one of the things that I was quite proud of that Hubert told me at the time, of moving me up the ranks at probably a quicker pace and many people would or would want to even, was that you have this ability to sort of scale at the pace of a fast-growing company. And this is a very rare thing. It was something that stuck with me because it was very nice, and it meant a lot. But as I thought about that, I knew that it was something that, as a leader, I wanted to both identify in others but also understand like what were the sort of qualities or the leanings that allowed someone to do that. And I wish I could say that I was deeply introspective at the time in terms of how I thought about my own career growth. I think one of the things that has helped to differentiate me in my career and that I've tended to fall back on is just work ethic and a little bit of that bias towards action that I'd mentioned before. I am absolutely like, by far, never the smartest person in the room. And usually like probably slower in other ways as well. Just as far as like the way people think about solving problems. But I'll outwork most people. I feel pretty confident about that, or at least I'm willing to match that pace.

And so as part of that, I think that's what helped me get to certain stages. Then how you go beyond that is really figuring out how to say 'no' more and learning how to increase your impact through the way that you help others, and how you find ways to do things more efficiently. And not just take pride in being the first one in the door and the last one out. And so as I thought about scaling myself and then scaling the team, I think it was, how do you sort of recreate that journey or at least identify that in other people in a way that folks won't burn themselves out or feel like they have to be doing that type of work in order to be successful in the job. Then also, find things that you can be really, really, really good at, and lean into those things. And don't be afraid to make that your thing, while also generally just maintaining that bias towards action - seeing a problem and asking for forgiveness, not permission to go solve it.

Go-To-Market at OpenAI

Alex Kracov: For the last part of today's conversation, I'd love to switch gears completely and talk about what you're up to now. So now you're on the go-to-market team at OpenAI. And so I would love to talk about why you joined OpenAI, and what do the sales look like at, I feel like, the most exciting company at the moment right now?

Conor Dragomanovich: Sure, yeah. So why I joined? I think I can safely say I was not alone in becoming deeply fascinated with generative AI. I would be lying if I said it was that fascination didn't explode around the time ChatGPT was launched. It had such an effect on me. It was one of those moments. When I first used it, I can actually remember where I was at the time. That's how impactful it was. And so it sparked in me all sorts of different emotions. But what I knew above all else is that I just need to learn as much as I can about this and about the world of generative AI. And so, of course, that led me to being exposed to so much of the work that OpenAI was doing. And of course, they've been doing that work long before ChatGPT was launched. And so I joined not only because I really genuinely felt like deeply fascinated by that work - I believed in the mission of creating safe and artificial general intelligence that's benefiting humanity - but also because I was researching the people who are joining this company. And that alone would have been enough to create a very strong pull for me to join.

Sales. What does sales look like at OpenAI? That was the second question, right? It looks busy. I can tell you that much. I think I was surprised at the time of joining like how small the go-to-market function was relative to the rest of the company, which is built around research and deployment. Of course, I joined around the week that ChatGPT Enterprise was launched. And so that was a busy week. So our sales team is focused on ChatGPT Enterprise and our API platform. That's really like the two, two of the products. The mission is how will we think about understanding the economic impacts that our models have on businesses and users and the way that they interact with them. So when I think about sales at OpenAI, like this small but mighty and growing team, it's focused on working very closely with customers who are either looking at ChatGPT Enterprise to create these massive productivity improvements, but also the API where customers are layering generative AI into existing products or building entirely new ones. And so there's that element of sort of like selling these products and helping them solve problems. But also, it's this piece of, how do we understand how people are engaging with this technology? So to that end, it's been incredibly rewarding and exciting.

Alex Kracov: How deep of a technical solution are you having to go in this sale? Because I imagine, like Dock - I mean, I assume you're working with bigger companies than Dock. But we'll use us as an example. We want to use OpenAI's API to build some products off of it. Are you selling to engineers and product managers and talking through, okay, here's some ideas on how you could build it, or here's some x samples? Then obviously, the cost of it is very interesting, right? Okay. How much are these credits going to cost me as we scale? That's something I'm nervous about too, even as we explore this type of functionality at Dock. So how do you think about that balance? Are you just talking of commercial terms? Are you talking about technical solutions? What does that look like as you start to interface with customers?

Conor Dragomanovich: It's definitely all of the above. I won't pretend that it doesn't require at least a relatively deep technical sort of sophistication. In some cases, there are specializations. I mentioned ChatGPT Enterprise and the API platform. And we have folks that specialize in each one. My focus is more on ChatGPT Enterprise. And the beauty and value of that product is that it's making generative AI more accessible in that way. So many people use it. It's because it's very natural to come in and use natural language and just put in a prompt. And, of course, there are degrees of sophistication that you can use it as one learns prompt engineering and other things. But there is an element of simplicity, both to the conversation to the product and to the sale that makes something like ChatGPT so compelling.

Alex Kracov: I mean, it's an amazing demo, right? That everybody's already experiencing and playing with. So that definitely must help the sale as well.

Conor Dragomanovich: Yeah, it does not hurt.

Alex Kracov: How do you think about selling into such a dynamic and evolving landscape? I mean, it's crazy how much is changing with AI. I could barely keep up with the news. I'm sure you could barely - it's just so hard. New competitor, new thing. It's just so much newness. And so how do you think about selling at such an evolving landscape?

Conor Dragomanovich: Yeah, I don't think anyone can keep up. I think anyone that either A says they can keep up, or B says they sort of know what's going to happen, I'm a little skeptical of. But I only look so far into the future because of all the aforementioned reasons. No one knows with 100% certainty what this will look like in one year, let alone five. For me, I tend to just treat it as a student, in that there will always be problems to solve. And the more I learn, the more my approach changes. The tools that I use will evolve, and the challenges are never going away. So I think it's obviously in our nature to just continue pushing the envelope. That will be true of the technology. And my focus is always like, as it relates to how selling evolves in this landscape, learn as much as I can, and continue this exercise of considering how I can use what I learned and then apply that to solving the new and exciting problems. It's certainly those that I have. It sounds sort of simple and high level, but it's really all anyone can do, I think, as well in terms of just keeping themselves apprised of what's going on. For my part, I'm excited. I know some people will have a different reaction, and I think that's very fair. But for my part, that's exciting.

Alex Kracov: Yeah, I think positioning as a student is really well said, and that's kind of how I want to think about it as well. Because as we think about Dock's product, and we want to add some AI in different places and think about how do we take advantage of that technology, I'm nervous about picking the wrong thing. It's going to cost a lot and whatever. But all of that doesn't matter because you just got to start trying and getting good at it and start to understanding how to use it. And even if you pick something wrong, or it starts to get expensive, or whatever the problem that might come, you're still making more progress and iterating towards this future. And as long as you're just learning and pushing in that direction, I think we could build a better company around that if we just have that kind of growth mindset mentality. So that's how I'm thinking about it.

Conor Dragomanovich: I think that's exactly right. I speak with customers all the time who are really excited. But they have this - there's this challenge that's not even unique to ChatGPT or anything where they just have so many use cases. And there's this question of, where do I even start? A lot of where our guidance starts is just start using it, to your point. I think there's so much to be said for even just this zero to one of getting comfortable with using generative AI as companies think about ChatGPT or any technology as it relates to generative AI. Those are really critical early steps, and there is so much value in just getting that initial exposure in giving that to your organization. The folks that tend to embrace that mentality, you see use cases explode very quickly. So that's been a really interesting learning.

AI and GTM Sales

Alex Kracov: I'd love to end today's conversation in talking about the intersection between the AI and go-to-market in sales. How do you see generative AI impacting the sales function and potentially other go-to-market functions already today? Then where do you see it's going to keep evolving in the future?

Conor Dragomanovich: I mean, I am so far from the expert, so this is just one ignorant opinion. But you know, I see it. I don't think it'll be unlike how computers reshaped knowledge work. I won't speculate decades into the future. But I see this impact where suddenly we have an even more incredible technology at our disposal, which ironically is letting us spend more time with the actual humans that we're working with. There's this concept of ChatGPT continuing to act as this orchestration engine for work. And I think that will be true of this technology as you think about the ways it can do so much of the work we wish we just didn't have to. That is going to free up time. We always find something to do with that time. I don't think there will be many of us just chilling in Bermuda. Maybe if that'd be the case, that'd be awesome. But I generally believe that at least one of the goals with generative AI should be to create more time and space for that to do the things we actually want to do and the things we want to spend time on. I think that will be true in the world of work, and I think that will be true in our personal lives as well. I don't know when we'll get there, and it's just my opinion.

Alex Kracov: Well, thank you so much for the wonderful conversation today, Conor. I appreciate you coming on.

Conor Dragomanovich: Yeah, thanks for having me, Alex. It was great.

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