Transitioning from Engineering to Product Leadership with Megh Gautam, CPO at Crunchbase

(Intro Narrator at 00:00:00) Today, we're talking to Megh Gautam, CPO at Crunchbase, about his journey from engineering to product leadership. You're listening to Joel Beasley, Modern CTO.

(Joel Beasley at 00:00:16) Now, a lot of the reason why people are listening is because they're trying to grow as a technology leader. And I was curious, what's your trajectory? How did you go from individual contributor to the technology leader you are today?

(Megh Gautam at 00:00:31) Yeah, I think a large part of this has been just the mindset that I've had, which is if you're not learning, you're not growing. And so I would still like to believe I'm still learning how to be the leader that I would be proud of. But I started in technology. I was an engineer. I was at Microsoft for about three years. Then I decided I wanted to move into more product management-y work, which is basically, why are we doing the things we're doing? Like, why is performance important? Why are we writing this particular line of code this way? And those fundamental questions you can only answer when you get really, really close to a customer.

(Megh Gautam at 00:01:12) And that's what got me interested. And then I had tours with startups, companies that I worked at got acquired. Then I went to—I did the public company tour. I was at Dropbox. I was at Twilio. And then I found myself here at Crunchbase. And I'd use Crunchbase, I think, every single company I've been at because it is the definitive source of private market information. And so it was just really, really helpful to be back and see things from the other side and be like, hey, if I were using this, what would I really like? And that's led me here to my journey.

(Joel Beasley at 00:01:49) So when you made that transition from engineering to product leadership, what are some of the mistakes that you made?

(Megh Gautam at 00:01:56) Oh, too many to list. Too many to list. I always thought that if I had this really cool, elegant idea that would shave off some time, or because of my engineering background, I'm going to be amazing at figuring out the solution and be the first to go deliver it. So classic biggest mistake I've ever made is, oh, I've become a product person. All the ideas must necessarily come from me.

(Megh Gautam at 00:02:27) And I think it took a manager just pulling me aside and being like, that's not how it works. Right? You don't have to try to suck the oxygen out of every conversation. Those were the exact words he used. And I was like, yeah, that is what I'm doing. And learning that and getting comfortable with the fact that you're more of a facilitator versus just the person who's imposing their will on a conversation has been a core learning. And two is the classical mistake I think everyone makes, which is spend too much time on the solution, not enough time on the problem. It's the whole old proverb, right? If you had two hours to cut down a tree, you should spend the first hour and a half sharpening the axe, or some similar metaphor.

(Joel Beasley at 00:03:15) So those are the two big takeaways from your transition. And then how long ago was that? Give me some understanding of time frames. When did you make that transition from engineering to product leadership?

(Megh Gautam at 00:03:26) It's been about a decade at this point.

(Joel Beasley at 00:03:30) About a decade. And then if there's someone listening right now that's either already made the transition or they're thinking about it, what would you say to them?

(Megh Gautam at 00:03:40) I would really counsel them on two things. One is time spans are a real thing. But if you could figure out what parts of this job or this role do you really enjoy, just test it out. Because you need to know how you feel when you're doing this job. And a large part of initially when I got interested in the product world was, this is a cooler thing to do, or there's less of these people. And it's very much the games that we play inside our heads, which is, do people want us to be this, or do I want me to be this? And so to a person watching, I'd be like, hey, test it out. See how you feel at the end of it. Do you actually like who you are? And then do you like what you do?

(Megh Gautam at 00:04:31) Because a lot of it goes back to identity, which is I think that the work that I'm doing makes me feel good about myself. And that is a huge part of being successful at the role that you're doing, especially if you're at the intersection of product, design, or even engineering.

(Joel Beasley at 00:04:48) How did you figure out that? I've come to the same conclusion about identity driving everything. How did you figure that out?

(Megh Gautam at 00:04:56) I got into places where I was like, I should feel really good about the work that I do. And then I was like, I actually don't. And a lot of it was, oh, there are stints and there are places in your time where even if you're given the opportunity, you would not capitalize on it because you haven't built up your own conviction in the work that you're doing. And to that part of myself, the only advice I offer is just go for it. The worst that you can have is, hey, you took your best shot and it did not work out. But the worst thing you could do is to go at it with, I don't know if this will work or not, and then just try to get to a spot where you're not fully committing. It's the whole, do or do not. There is no try. Just commit fully and do it.

(Joel Beasley at 00:05:44) Come on, Yoda. Exactly. Exactly.

(Joel Beasley at 00:05:48) So you said time spans. I've never heard anybody actually—it's somewhat intuitive what it means, but I've never heard anybody phrase it that way. Can you explain to me what time spans are?

(Megh Gautam at 00:05:59) Yeah. So in terms of, we have just as humans, right? We're like, hey, I'm committing to this job, and this is me for the rest of my life. And that almost never is the case. So you could basically take some time and you're like, in this season of my life, I want to experiment or I want to explore. And once you put that spin on it, it becomes much easier for you to spend your time and try to do your best knowing that, hey, this is not what you are signing up for the entirety of your life.

(Megh Gautam at 00:06:38) An old colleague of mine was really good at this where you're like, hey, you have to do tour of duties, or you have to understand what you're inherently good at. And there's various different ways of saying it, but it's essentially that. It's like you have the permission to try something different with the full intention of, you don't know how it's going to work out for you.

(Joel Beasley at 00:06:56) Interesting. So for people who are thinking about making that transition, engineering to product leader, one way to frame it would be, I'm just going to—I'm not going to take the opportunity. I'm just going to double down on what I'm good at, and that's one frame. Another frame can be, yeah, I think this is a good opportunity. I'm going to give it a shot. I'm going to go into it knowing that this is just a season of experimentation and seeing how it goes. And if I don't like it, I can always just go back to what I'm doing now. Would that be accurate assessment? Okay.

(Megh Gautam at 00:07:25) Totally. And I think if you look at companies of the past, there used to be these rotational development programs where you could spend some time in analytics or marketing or engineering. And then you could come back and you're like, I have spent six months in each of these disciplines. I really like that department the most. And you're making a thoughtful decision based on time spent. And that, I don't think it happens as much these days. But certainly, as you go along in your career, it happens even less and less, which I think counterintuitively is why a lot of people like startups. Because they go there and you're like, hey, many different hats to wear. I don't have to specialize. And I think it's a core reason why people enjoy the fact that you can work across different functions and truly see your impact across the board.

(Joel Beasley at 00:08:17) Well, another thing that wasn't so clear to me was when you're evaluating it, you typically look at the role and responsibility, like how I'm going to be spending my time. That's one vector. The other vector, though, is the people who are naturally attracted to that type of work, like personalities. And so there's been times where I'm like, oh, it'd be really cool to do something over there. And I went over to that sector—I'll share personally. Specifically, it was HR leadership software, and so you have to sell to HR. And I started spending a lot of time with the HR people, and I'm just like, these are not my people. There's nothing inherently bad about them. It's just the people who are attracted to that job are just not my people. And so instead, I found, you know, where the mix of the work that I find interesting and enjoy doing and the people I like to spend time with. So to your point of tours of duty, it's going to give you exposure to that work, but also exposure to the culture of the people that are currently doing that work.

(Megh Gautam at 00:09:15) Totally. I could not agree more with you. And I'll kind of improv and go yes and on this, which is it's the kind of customers that you're serving. Is it enterprises? Is it small businesses? Is it mom and pop shops? Is it a person? And I found myself really struggle to get an idea of what a person who gains a lot is intrinsically motivated by. So if it's a consumer mobile app or if it's a consumer video game, I actually don't think I relate well to this particular population, which means I can't empathize, which means I don't think I'm going to be good at this. And so in addition to the kind of people whose lives you're making better, because we spend so much time working, it also is, how are you reaching them?

(Megh Gautam at 00:10:03) Is it direct? Do you spend months in the sales cycle to sell a hundred K deal? Or is it just swipe a credit card? That also matters quite a lot because some people are just oriented towards, oh, I'm just going to move this jigsaw puzzle here, and it's going to complete the whole puzzle for me, which is a lot of enterprise sales. And some people are like, yeah, you know, I'm just going to figure out a way to make distribution work. TikTok videos and money comes in. It's just a whole different motion there.

(Joel Beasley at 00:10:34) And you've got to try things. I wish I could tell you I had the answers. I don't. I'm still experimenting. Because the problem is I change. Yeah. Exactly. I find things that I like, and then I achieve a level of mastery, and then my interest changes and then I'm back to the experiment. It constantly feels like I'm going back to square one that at the same time, if I check my net worth, I'm like, okay, well, clearly I'm not screwing up long term, but right now, I feel horrible, you know. And then I've just got to figure out how to reduce the distance between feeling bad and feeling good again.

(Megh Gautam at 00:11:10) Yeah. I mean, I think the number of times that I end up picking up some intro to something article, because it's not just you. You definitely change and grow and mature and the things that you find interesting change, but also the market all around you. The market changes, it's shifted, everyone values this other thing now. Or AI and foundational models were not a thing three years ago outside of a very specific audience. But now they're everywhere. My mom called me yesterday and she's like, will this AI thing take all of our jobs? I was like, how is this the dominant social conversation which we're having? So there's a lot of variability, and the pace of change is just crazy.

(Joel Beasley at 00:11:53) But it definitely is going to. Now, I just—I stumble across something. I've got a nice group of friends that I've known for ten plus years and we're all in tech and we text each other back and forth and I have found, if I were to chart the progress of that text, I am texting them on a multiple times a week, two plus times a week at jaw-dropping discoveries that I'm seeing in the marketplace. Whereas two years ago, three years ago, it was, I don't know, once every month or every quarter, there was something good to share. Have you seen this trend of these—they're calling them digital employees now. Have you seen this? They—that one dude yesterday just wrote, raised $20 million or $40 million from Andreessen Horowitz to scale up, but they're no longer selling you the CRM software, right? As here's CRM. Here's features. They're selling you Bobby. And Bobby can achieve these outcomes, and then you pay for Bobby to achieve them, and you just let Bobby work autonomously. That is insane. That's the future.

(Megh Gautam at 00:12:58) I agree with you on your first point of just the pace of innovation has been game changing. The thing that blew my mind was how quickly these video avatars went. If I look back, I was like, okay, the hands are weird. Right? There's always a sixth finger or something, and those are pictures. And now all of a sudden, you have a remarkable talking head video. And I think I was using one of these AI video gen companies. And it's really, really good. But to your point, right, I think the marketing is brilliant of these things, which is we sell you the work. Don't worry about the seats. Don't worry about SaaS. We're going to sell you the thing that you care about, which is are you getting more leads? Are they coming in? Are they qualified?

(Megh Gautam at 00:13:43) And I think it's this correction against SaaS software trying to sell seats for every employee. And then that pivoted to usage-based pricing, which is you just pay for what you use. And now you're seeing this marketing moment connect where you were like, we will do the thing for you. Do not worry about it. And you have hired this thing to do the job for you. It's this perfect mix of the technologies kind of getting there. The reaction from the buyers has been like, we can't pay for everyone to have 12 different types of point solutions. And just the way that the macro is working right now, where it's like, we just have to get super efficient.

(Joel Beasley at 00:14:27) Yeah. And I want to get into the new AI developments. And I was a customer of Crunchbase for many years, and I want to get into all of that. But before we do, I just want to see if there's anything more at all to add. I'm going to sell this as a master class, essentially, when I put it in the title on transitioning from engineering to product leadership, right? Be like, this is the guy. You shared a ton of good insights. Is there anything else you want to get out there to the world about that transition?

(Megh Gautam at 00:14:58) I still fall into this trap today, but it's like if you are transitioning or if you're thinking about transitioning from engineering to product, you have to like talking to people, and you have to spend time with your customers. And the interesting thing is everything about the whole history of product management—oh, you have to be agile, you have to do this thing, you have to write this other backlog. All of those activities take you away from talking to your customers. And so if you think that you have saturated talking to customers or that's the thing you don't inherently enjoy, you still have more conversations to get to. And it's probably not the right field if you don't enjoy talking to customers about their end goals because, until, you know, things massively change, it's still solving a human problem, which is a business problem, delegated to a person.

(Joel Beasley at 00:15:56) Very cool. You get it, man. I like you. Thank you so much for listening. And if you found this episode useful, please share it with a friend or colleague who you think would get value from it.

(Joel Beasley at 00:16:07) And if you have topics that you'd like to hear discussed on the podcast, either add me on LinkedIn or send me an email, [email protected]. Every time I get an email or LinkedIn message, it absolutely makes my day and inspires me to keep going.

(Megh Gautam at 00:16:25) [No spoken content]