What this $2.45B CPO knows that you Don’t!

1. JEJeremy Epling0:00

   I would say one of the mistakes I made from my perspective was just not leaving Microsoft early enough.

2. AGAakash Gupta0:05

   What is really the secret sauce behind Vanta's success?

3. JEJeremy Epling0:08

   This process is extremely hard and, you know, takes months and months and, like, a year or more. It costs $100,000 or more, and we're like, "Hey, how can we bring software automation to this?" I mean, think of when you look at new tools coming out, whether it be, like, Lovable or V0 or Bolt. We actually have V0 licenses for every PM on my team.

4. AGAakash Gupta0:26

   How did you-

5. JEJeremy Epling0:26

   Yeah

6. AGAakash Gupta0:27

   ... make those steps up the career ladder?

7. JEJeremy Epling0:29

   I remember the first promotion I got at Microsoft, and I remember one of the things my manager said with me that obviously I've never forgotten was like, "You're getting this promotion because you've, like, learned how to say no." [laughs] I had a small startup before that and a small business where I had, like, been building websites for companies and things like that, like, in college and high school, and then I came in and just felt very divorced from customers. Even though I do have, like, a really long tenure at Microsoft, I never stayed on a team, I think, for more than, like, four years. I wanna go learn something new. I wanna go learn how to do a V0. I think for GitHub, they have a bunch of cool tools for PMs to think about, you know, whether that be Copilot, some of the agent stuff that they're doing. People should be playing with, just like they should all these other tools. But I think understanding the developer workflow, how software is built. Encouragement for engineers and even for PMs when you're talking to engineers is just ask them the why if you don't understand. Like, why do you wanna go do this thing?

8. AGAakash Gupta1:19

   When you were working on Outlook-

9. JEJeremy Epling1:21

   Yeah

10. AGAakash Gupta1:21

    ... another billion-plus user product, can you bring us back? What was a day in the life like as a Microsoft PM on Outlook?

11. JEJeremy Epling1:29

    I mean, I think a lot of the day in the life was, I remember having big debates of, like, you know, when we were-

12. AGAakash Gupta1:35

    Really quickly, I think a crazy stat is that more than 50% of you listening are not subscribed. If you can subscribe on YouTube, follow on Apple or Spotify podcasts, my commitment to you is that we'll continue to make this content better and better. And now on to today's episode. Jeremy Epling is one of the most senior product leaders in the Triangle. He's worked at GitHub, Microsoft, and now he's the CPO at Vanta. Welcome to the podcast.

13. JEJeremy Epling2:03

    Oh, thank you for having me. Excited to be here.

14. AGAakash Gupta2:05

    So you worked on Internet Explorer when Internet Explorer was cool.

15. JEJeremy Epling2:09

    [chuckles] Yeah, definitely. Uh, in the, like, early 2000s, I was there and got to work on a bunch of really exciting new features which seem kinda old hat now, but tab browsing was, like, brand new at the time, working on tab grouping, all the different associated features there, thinking about, like, browser extensions and where we go. Also dealing with standards around, like, privacy, HTML, where do we wanna go with that in, like, the early days. Um, and yeah, it was a really exciting time 'cause so much was changing, and this is way before Chrome came. Firefox was just starting to become a thing out of Mozilla. Um, and yeah, just a ton of competition, uh, and really kind of exciting innovation going on on the web.

16. AGAakash Gupta2:50

    So when I was a PM in the late 2000s and early 2010s, it was very waterfall. I wasn't very connected to my customers, and my entire life revolved around writing 20-page PRDs.

17. JEJeremy Epling3:02

    Yeah.

18. AGAakash Gupta3:02

    Is that what life was like for you as a PM?

19. JEJeremy Epling3:04

    Yeah, it was pretty similar, and it was actually kind of shocking at first when I came there. Like, I had a small startup before that and a small business where I had, like, been building websites for companies and things like that, like, in college and high school, and then I came in and just felt very divorced from customers. And I remember even seeing that first spec template, we called them, at Microsoft, and it was like 20 pages, just, like, the template to go fill out, and I was like, "Is this how software development is really done?" Obviously, it's not at all how we do it now and definitely not how we do it at Vanta. Um, but yeah, at the time, it was very inward-focused, you know? It was like, "What did we think was best for customers?" You felt very detached from customers. Um, and I felt like PM, at least for Microsoft there, you did a lot of other roles. You were leaning a lot more into kind of design, sometimes doing your own designs depending on what we had, spending a lot more time with engineering. I felt like your scope was much smaller, too, which is something we do differently at, like, Vanta, where we try to give PMs really broad scopes, and I actually try to have, like, a very thin, light PM team so they can have even broader scopes and own more of the business and more of the scenario there. Where I felt like at Microsoft at the time, a lot of new PMs would start, and you were, like, only paired up with, like, three engineers. And it's like, I felt like half the time I was, like, distracting them from what they should be doing, you know what I mean? And, and so felt like we were too hands-on and too prescriptive back then.

20. AGAakash Gupta4:17

    Yeah. I think that is a lot of broad trends in the industry, and just in that one example exemplified, especially the one around PM-to-engineering ratio. And I think that people are wondering, like, "Is that ratio gonna continue to increase, where PMs support more and more engineers?" Is that kind of the s- Have you seen a straight-line trend through your career on that?

21. JEJeremy Epling4:38

    Yeah, definitely. I mean, I think that's the way it should be going. It's definitely the way I'm leading our engineering, product, and design teams. I mean, I think of when you look at new tools coming out, whether it be, like, Lovable or V0 or Bolt, we actually have V0 licenses for every PM on my team, and it has been transformative. Even PMs that don't come from a technical background like me, that, like, stuttered computer science and still write code to this day, they're able to go in and really quickly build prototypes and share those with customers and get that really fast feedback loop. Is it the most well-designed, perfect thing that our design team would build? Like, no, not yet at least. Maybe it will get better there, but it's enough to show a customer and get a reaction. I know I have, like, a lot of catchphrases internally. One of mine is kind of like, "Seeing is believing." And I think one of the key things is it's awesome to get a great PRD or, like, a strategy doc around what we should be doing and why, but I don't really know what it means until I can experience it. And so I think the fact that people can prototype so much more quickly and get that into real code that's interactive has just been transformative. And we've had PMs, especially if they're slightly technical, be able to build very deep, like, walkthroughs very quickly, where you can really start to feel the experience and, like, the UX of it. And then, you know, P- PM or design can pair up with them. But I do expect PMs to be covering a broader area. I see, like, a merging of design and engineering, especially on the front end. Like, we see some companies having design engineers now. We're seeing designers even starting to do pull requests. It's something we're talking on within our team about how we get more there. Um, so I do think the whole notion of how engineering, product, and design work together is completely changing right now.

22. AGAakash Gupta6:13

    Yeah. Everybody's been asking me, "Do you know of any orgs that are actually using these AI prototyping tools?" So now that I have a CPO who is asking his team to actually use those orgs, and as you said, you lead product design and engineering, so you're not coming at it from just a PM point of view. What are the right ways as a leader to give the right guardrails for people? Because I think historically, when PMs got into design, design could get a little bit protective, and same engineering could get a little bit protective, and for good reasons, of course. But how do we correctly give the guidance to teams about where the handoff points should be?

23. JEJeremy Epling6:50

    Yeah. I think the, the more kind of overlap, the better in a lot of cases. But I also am very comfortable having teams work differently. Like, uh, some teams, we have PMs that are, like, very strong on the UI side, right? And, like, want to spend more time there. Or we have some that are really strong on the technical side. Or we have engineers that are just amazing product engineers and can kind of run on their own to, like, a large degree and think about all the different pieces. So I look at it as a team by team and, like, let there be different shapes as opposed to, like, one template that has to work for every team. Um, I do think, um, when I think about some of the boundaries, like, I believe, like, design fundamentally should be accountable for the experience, and I'm excited to have them deliver more of that experience over time. Like, when I've talked to friends of mine, like at Vercel, like I'm good friends with Manuel there, who, like, leads design. And I know one of the things he does is he actually owns a lot of the implementation of the front end, and that's something we've been playing with more. I don't know if we'll go there, you know, immediately for our design team doing that, but design and engineering working even more closely together is something we're spending a ton of time doing. And design really feeling that accountability for the quality and craft of what's delivered and not just, "Hey, I delivered a great Figma file," and, like, "I'm done. I'm on to the next thing." But, like, did it show in the product? And I think as a designer or a PM or even as an engineer, what's exciting is actually shipping. You know what I mean? It isn't the, like, "I delivered a great design, and I hope someone implements it. I feel good." Like, I wanna get that product in the hands of customers. I wanna see that delight and excitement. And so I think that's one of the things for me. So for PMs, I think them being able to prototype, but then not having to kind of obsess on the exact UI, and then partner with the designer that could ideally even collaborate in these tools. And that's one of the reasons why I think, like, Lovable has an interesting take on this because they're not just looking at it from the standpoint of AI chat only. 'Cause, like, I can tell you, when I wanna move a button from the left side to the right side, I don't wanna go have to go describe in chat. Like, "Go target this thing and please move it over here under this and do that and change the color to that." I kinda just wanna click on it and drag it and move it. And so I think we're gonna see a blend of these UI paradigms there where there's direct manipulation there. We're spending a bunch of time trying to figure out how do we translate from V0 or, um, or Lovable or Bolt or any of these things directly into cursor code and then getting that directly kind of into GitHub, which is what we use for, like, our code repository and actions for building and testing and deploying. And building that pipeline I think is gonna be really exciting and change kind of who does what. So I expect the breadth of PM to grow, and I think this, it'll be the same for design as well. As they get these tools that can help them move faster and prototype more quickly, there's just a huge opportunity. Like, design systems, like, I just wanna be able to upload our design system into, like, Figma or, you know, Lovable or one of these tools and then just be able to, like, describe what we want. And I think divergent thinking is a really big thing in, like, design overall. I'll say design a lot, but I don't necessarily mean it has to be the product design team doing it. But I love looking at things where it's, "Hey, can I see five different versions of which direction we should go do? And then let's whittle it down to, like, two, and then let's get to one."

24. AGAakash Gupta9:56

    Hey. Let me take a quick break to talk about something that's completely changed my product management workflow: Linear. As a PM, I was drowning in tools, one for planning, another for issue tracking, roadmaps and sheets, and jumping between Slack, Intercom, and app reviews just to piece together customer feedback. Sound familiar? I was spending more time keeping systems in sync than actually building product. Every time development kicked off, my carefully crafted plans would immediately need updating. I was the human API between all our teams, constantly chasing updates and translating between tools. That's why I love Linear. I can capture customer feedback, shape product ideas collaboratively, quarterback cross-functional teams, and monitor development progress in one place. It cuts through the maze of disconnected systems that were complicating my life. Product teams at OpenAI, Vercel, Brex, and Cash App all use Linear. If you're tired of spending your days keeping different tools and teams in sync, check out Linear at linear.app/partners/aakash. That's linear.app/partners/aakash. Today's episode is brought to you by Amplitude. Building great digital products is hard. You know that better than anyone. Getting teams aligned, measuring what matters, and scaling your product strategy isn't easy. But what if you had a clear framework to guide your next steps? That's exactly what Amplitude built. They studied the best product teams to understand what really drives impact and turned those insights into the Digital Experience Maturity Assessment. In two minutes, you'll be able to see where your team stands and what you can improve to build better products faster. Click the link in the caption to take the free assessment and get a clear path to product growth.

25. JEJeremy Epling11:23

    Where I think a lot of the time when people try to go find the one idea and take it all the way to perfection, you get too much personal identity attached to it. It's hard to take feedback and criticism, you know, because it becomes tied to you versus like, "Oh, I did these five different things. Which one do we like and how do we get down?" And being able to explore more breadth of options more quickly I think will be really powerful, and then translating them into code, um, more quickly with AI tools. And they're not perfect, you know. There's times when, like, I'm using, you know, any of these, whether even, like, I had this experience with Claude the other day where I was working on some code. I was, like, writing something, and I was like, "I know this is wrong," and I even typed back to it. I was like, "I think this is wrong. This interface doesn't exist. What about this?" And it comes back and it's like, "Yeah, you're right." [laughs] Which I just found to be this, like, silly experience. But they're getting better and they're learning, and I think we'll be able to move a lot faster with all these tools.

26. AGAakash Gupta12:11

    So anyone who's listening to this podcast knows I can talk about AI prototyping tools for the whole podcast.

27. JEJeremy Epling12:16

    [laughs]

28. AGAakash Gupta12:16

    But I wanna turn back the clock again to your next role after Internet Explorer. When you were working on Outlook-

29. JEJeremy Epling12:22

    Yeah

30. AGAakash Gupta12:22

    ... another billion-plus user productI don't think many people get the opportunity to work at that type of scale. Can you bring us back? What was a day in the life like as a Microsoft PM on Outlook?

Episode duration: 1:19:37