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

1. 0:00 – 2:05

   From Microsoft to Vanta: a career “too comfortable” at BigCo

   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.

2. 2:05 – 2:50

   Internet Explorer era: shipping browser innovations amid web standards battles

   1. AGAakash Gupta2:05

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

   2. 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.

3. 2:50 – 4:17

   Old-school Microsoft PM: waterfall specs, distance from customers, narrow scopes

   1. 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.

   2. JEJeremy Epling3:02

      Yeah.

   3. AGAakash Gupta3:02

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

   4. 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.

4. 4:17 – 11:23

   AI prototyping and the new EPD operating model (PM/design/engineering overlap)

   1. 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?

   2. 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.

   3. 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?

   4. 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."

   5. 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.

5. 11:23 – 12:16

   Divergent thinking: explore 5 options, then converge—and be honest about AI limits

   1. 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.

   2. AGAakash Gupta12:11

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

   3. JEJeremy Epling12:16

      [laughs]

6. 12:16 – 15:30

   Outlook at billion-user scale: protocols, threading, spam, storage, and privacy tradeoffs

   1. AGAakash Gupta12:16

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

   2. JEJeremy Epling12:22

      Yeah

   3. 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?

   4. JEJeremy Epling12:35

      Yeah. I mean, it was interesting. I think one of the unique experiences for Outlook was it was actually split across two different Microsoft sites. So I actually got my first feeling of, like, remote work and working with remote teams. Like, when I was on Internet Explorer, everything's just based in Redmond. You're there working with people in the same office. Um, a lot of the Hotmail team that built the backend for what became later called outlook.com was actually all in Silicon Valley. So I'd be flying down there, meeting with them consistently, and then we built a lot of the client experiences and some of the server experiences, uh, inside Redmond as well. So getting used to kind of, like, that travel, working remotely, doing that. Everyone knows how to go do it now, obviously, after COVID and everything, but it was definitely a new thing when I think about that in, like, the 2000s when we were doing it. Um, I mean, I think a lot of the day in the life was a lot of work on scale, I think was a big thing for us on, you know, the backend and then even on the client. I remember having big debates of, like, you know, when we were working on a new version of the Mail app for, like, Windows 8, you know, and trying to figure out what we should do for, like, Outlook there of, like, should we support POP or IMAP, and, like, what is the future of those and these different protocols? Which is, like, very silly in retrospect, but definitely we took the forward-looking approach of IMAP, where it's like the protocol basically allows you to say if you mark it unread on your client, it will be marked unread there, and automatically having a two-way sync versus people can remember back in the day of POP, like, you just downloaded emails, and when you deleted them locally, they were still all sitting on the server, so when you connected the next client, you just kind of, like, didn't have any state that roamed. So building those features, thinking about threading. Like, there wasn't conversation threading. That was, like, a big, new feature I remember working on of, like, "Oh, okay, great. How are we gonna do this? How strict do titles need to be the same? How do we think about, like, mapping, and what other indicators can we get for replies to do threading?" And making sure when you're threading that you're actually getting the new unique content. You know how everyone expects in Gmail or outlook.com to kind of hide the back and forth, but that's still in the email body. So how do you detect that section? This is actually when we started experimenting with machine learning. I'd say some of the earliest machine learning at Microsoft, and I'm sure it was true at Google and everything, was actually spam filters and us trying to identify spam problems. That was one of the biggest issues there. Email storage was a huge issue. Like, you had to think about your 10 megabytes- [laughs]

   5. AGAakash Gupta14:49

      [laughs]

   6. JEJeremy Epling14:49

      ... that you were managing and how you were deleting things and not there. Obviously, Google completely changed that with, like, launching Gmail and, like, rethought the whole model of effectively infinite storage. Um, but yeah, I felt like those were a lot of the problems we were wrestling with is, like, these new features, helping people communicate quickly. Um, and then there was this whole notion of ads. Like, how much can we push ads from a revenue side in the business? Can we read people's email? Is that okay? Is it not? Is it just a displayed ads business? We knew that, you know, if we could look into the email and give more relevant ads, you know, you'd have better click-throughs, and you could drive more revenue that way. But then you had the big privacy implications, so I remember having lots of debates around that and where we should go.

7. 15:30 – 17:56

   How Microsoft built features: PRDs, technical depth, and global readiness constraints

   1. AGAakash Gupta15:30

      Oh my gosh, so many awesome features. So if we were to break down a feature like threading, for example, how does Microsoft really build that feature, you know? Is it, like, I guess Steve Ballmer at the time- [laughs]

   2. JEJeremy Epling15:41

      [laughs]

   3. AGAakash Gupta15:41

      ... is like, "We need threading," and then it-

   4. JEJeremy Epling15:43

      Yeah

   5. AGAakash Gupta15:43

      ... slowly works it way down the execs, and then it's split up amongst twen- 10 PMs, or how did a feature like that get built?

   6. JEJeremy Epling15:50

      Yeah. I would say, I'd say my experience, I was there for, like, I think I was an intern maybe when Bill Gates was still the CEO, and then Ballmer and Satya, all of them were completely different. I felt like Ballmer's focus was really on revenue, and that was, like, his superpower in sales, coming from sales and revenue, but was pretty hands-off from my experience on, like, product in almost every way. So usually, that stuff kinda got delegated down. So when I, when I was, like, an IC PM, like, my lead or my GPM or something like that, we'd be having those discussions around which features and be like, "Hey, somebody ship something first." We'd be like, "Okay, let's go use the product, play with it." Um, in the case of threading, it was more just, like, an idea we had internally, and we're just like, "Hey, this'll be really helpful. Everyone hates dealing with this." So we kind of go write one of those massive PRDs, you know what I mean? Spend a w- weeks and weeks, like, researching in a very kind of, uh, waterfall style. Usually, there'd be, like, an engineering team you'd be paired up with, so you'd be spending a bunch of time with that. I was a more technical person. I felt like at the time Microsoft at least skewed that way, so I'd even be working on architectural diagrams around, like, "Okay, great. Like, what's the call flow patterns?" And reviewing those and, like, "How are we going to go scale this, and what type of storage do we need, and how much storage do we need for this?" So I felt like there was a lot of blending at that time. Um, you're maybe a little bit less business-focused, like revenue-focused, and more of, like, the feature down to the technical details around how would this work. And then because Microsoft does have, like, billions of people using the products, I felt like there were a lot of things you had to go do to make sure everything was market-ready everywhere, which to some degree slowed things down. Um, but it was like, "Hey, whenever you launch a new feature, it has to be in every possible language." Like, internationalization has to be there. I would have to define right-to-left languages and, like, what's our behavior here? Where are we flipping the UI for, like, RTL scenarios? Where are we not? It's like accessibility, think through all the details of that. And it felt like design, unfortunately, was kind of almost relegated to kind of being more of, like, colorist and visual only and not as much the user experience, at least the teams that I was on, which I think is completely different now and definitely not how I look at, like, how I want design on my team and how I think most people do.

8. 17:56 – 20:59

   How PM changed over 16 years—and Satya’s strategic reset at Microsoft

   1. AGAakash Gupta17:56

      Yeah. So we talked about some of the trends that have changed, but how would you summarize over 16 years at Microsoft, how did PM change?

   2. JEJeremy Epling18:07

      Yeah. I think one of the biggest ways it changed wasProbably some of the ratio stuff we talked about earlier, like having a larger span of control. You're working with more engineers, thinking about more of the business and these holistic experiences. Um, I think design got a stronger voice, which I think was, like, a very good thing around not just the, like, visuals and making it look pretty, but actually, like, what are the flows? What's the experience driving that partnership a lot more deeply? Um, I felt like at Microsoft too, especially by the time that I left out of Azure, there was, like, much more focus on the business and, like, a really thinking about, is this feature driving revenue? Is it not getting more connected with customers, more connected on sales deals? I did feel like even though when I left though, because Microsoft's so big and sells to so many large customers, you were very just focused on big enterprise deals. So, like, a lot of the time you wouldn't get as much hands-on time with, like, smaller customers, but you were very often brought into conversations with, like, big banks. What are their top requests? What do they need? I remember even, like, flying out to go meet with them and help them onboard. So I felt like we got a lot more tied to customers, which was great. The span of control kind of got bigger. Design got a stronger voice, um, which were all, like, positive trends.

   3. AGAakash Gupta19:20

      So a lot of the changes within Microsoft reflected the changes broadly within the industry.

   4. JEJeremy Epling19:25

      Yeah, I think so. I mean, I think they kinda happened a little bit slower than I would say were definitely happening at, like, other companies. Um, some of that's, like, steering the big ship takes a little bit of time, and I think part of it too was just Microsoft, I would say, in that era with Ballmer, invented lots of great revenue things that I'd argue he maybe doesn't get enough credit for, like enterprise license agreements and how to think about, like, software licensing and, like, a lot of amazing sales innovations that, like, drove revenue up, but the stock price never really moved. And I think that was because there was, like, very little focus on product and product vision, and, like, when it was delegated down, the beats weren't always there. You know, when I was there, Microsoft missed search, uh, it missed on mobile, you know. So those were, like, two huge trends to be, like, late to, and I think Satya came back and was, like, very clear on, like, what the priorities were. We need to go build a cloud. We're gonna go win here. Here's how we're gonna go win. You know, he quickly got all the Office apps on iOS and got them on Android and kind of pushed us to go everywhere and really, like, move the company forward to, like, a modern SaaS way of building and really focusing on the experiences and how to make it great for customers. You know, I think that was when Microsoft started to take hardware more seriously. Not that, you know, I think Surface has taken over the world in any way, but, like, definitely was trying to figure out how can hardware plus software really work better together in an ecosystem that's like Android, you know, which is kind of what Windows is, where you're working on lots of different hardware vendors and partners, um, and then trying to kinda do something more like Apple, where it's, like, deeply integrated.

9. 20:59 – 24:48

   Leadership lessons from Satya: clarity, experimentation, and successful acquisitions

   1. AGAakash Gupta20:59

      Wow. What are the lessons you learned from seeing Satya?

   2. JEJeremy Epling21:03

      Yeah. I mean, I think that I, I'm a pretty big Satya fan, [chuckles] uh, not just because I was at Microsoft for a long time, but I think he's just a great leader. Um, I got to have, like, a few different meetings with him, like, when we did the GitHub acquisition and, like, afterward and demoing some of that stuff and getting feedback on our internal engineering systems, which I was, like, leading a bunch of the work for for a while. Um, I think he's really good at creating clarity and priorities, and I think the company before him was often focused on, yeah, we need to hit the revenue goals, but it was kind of just like do everything all the time. And I think he kind of really went in and said, "No, these businesses matter more than these other ones, and we're gonna really right-size these efforts." Like, where are the growth opportunities that especially align with our strengths? You know, Azure was a big one where he's like, "Hey, we need to go win here." AWS was there first, but I think he really got us clearly of, like, we can win the enterprise business. We need to move all the server customers to the cloud. How do we go do that? How do we differentiate with more data centers, more data localization, um, being first to regulatory environments and doing that? And I think that was great. You know, he allowed us to experiment more, so, like, creating, like, VS Code and things like that, where it's like, hey, you know... That, that was very controversial, the team that was working on VS Code, like internally from my perspective. Because we had Visual Studio, and that's, like, a billion-dollar-plus business, you know what I mean? And you're, now you're like, "We're gonna give away some of that for free? Like, we're gonna build a new editor that everyone can just have for free? Like, what are you thinking?" And so there were a lot of business discussions around, like, what should go into one, what should go into the other, how we should go do it. But, I mean, it was a great engineering team and product team, design team that really just pushed forward and said, "Hey, we think this is transformative. We wanna go do it." And I felt like Satya was very embracing of these ideas. His approach to acquisitions, I feel like all of his acquisitions, I think, have basically been successful. Where I'd say before that, I'd argue, like, very few if none of them were. You know, Skype didn't really work out. Aquantive didn't work out. Some of the other ones. Um, but, you know, think about Minecraft. I think that was a great acquisition for Microsoft. I think all of his have been kind of rooted in social to some degree, so that was about, like, to my mind, it was, like, one, kids and education and that, like, social network that was created was big. Obviously, LinkedIn was, like, really big for, like, businesses and how to connect people and social and what can we go do there that plays to Microsoft's strengths, having Office and everything. Um, I think GitHub was, like, the other big one, the developer social network to some degree, and, like, winning back that developer community. I felt like he put a really big focus on Microsoft was started as a developer company, and we kind of, like, lost our way a little bit, and let's get back to being great for developers. And, you know, VS Code, GitHub, a lot of the investments in Azure to make it better, I feel like all line up there. Um, and I think there's a good strategy around that. Like, if I think about that, like, if you're an engineer today, um, you know, it's hard to, like, not interact with Microsoft to some degree. You know what I mean? It's like you're probably writing code in VS Code, or even if you are using Cursor or Windsurf or something today, it's still a VS Code derivative. You know what I mean? You're probably storing your code on GitHub. You're probably using LinkedIn to go get a job. You know what I mean? So if you think about a lot of what you're doing, you're probably using GitHub Actions to go build and deploy your software. Like, maybe you're using Azure, maybe you're not, depending if you're in their sweet spot for what they focus on versus AWS. Like, most startups, I think are pretty much all AWS, you know. Bigger enterprises probably usually lean more to, you know, Azure in a bunch of cases. Um, but yeah, I think that was a lot of his strategic insight, was, like, how to put these different pieces together and really complement the areas where, you know, Microsoft wasn't in social, so what do we need to go do there? How do we re-energize developers? Because that was, like, the roots of our company, and we just do so well. I think our, the company did so well when it did focus there.

   3. AGAakash Gupta24:41

      And it shows up in the stock price, right?

   4. JEJeremy Epling24:43

      [laughs] Yeah.

   5. AGAakash Gupta24:43

      I think when he came, it's almost like nine or 10Xed, I feel like.

   6. JEJeremy Epling24:47

      Yeah.

10. 24:48 – 33:23

    Climbing the PM ladder: saying no, cutting your own work, and broadening ownership

    1. AGAakash Gupta24:48

       So insane results from Satya there. When you were at Microsoft over those 16 years, that's when you really moved up the PM career ladder.

    2. JEJeremy Epling24:56

       Yeah.

    3. AGAakash Gupta24:57

       What were sort of the key ways you approached that? Because a lot of people, they'll often get stuck in the PM career ladder, where they don't make it past certain valleys or canyons, whether it's from senior IC to manager, or even you eventually, I believe, made it all the way to VP. Like, how did you-

    4. JEJeremy Epling25:12

       Yeah

    5. AGAakash Gupta25:12

       ... make those steps up the career ladder?

    6. JEJeremy Epling25:14

       Yeah. I mean, I think there was a couple things. 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."

    7. AGAakash Gupta25:26

       [laughs]

    8. JEJeremy Epling25:27

       And I thought that was, like, good advice that, like, I kind of maybe twist a little bit to talk about, like, creating focus or creating clarity. And I remember another promotion I got when I made it to, like, senior PM for the first time, and that was, again, because I was given a big problem to go solve in IE. This, uh, some of the extension stuff that I was working on and some of the other things, and I was like, "Hey, we should actually cut like half the work I'm working on." I had like 12 engineers assigned to it, and I was like, "We shouldn't be doing this. We should be doing this other thing as well." And I'm not saying the path to growing your career is, like, cutting things, but I think that so many people rarely will step back out of their area and be like, "Am I actually working on what matters?" 'Cause, like, once you get a team and a charter, there's this just natural, like, you know, momentum that happens of, like, you're just gonna keep doing the same thing and making it better and forgetting to be like, "Is this area actually still important anymore?" And it might be solved, or it might be solved enough, or the business might need to go somewhere else. And I think being able to step in and, like, be direct and make those hard cuts, even if it's your own area. 'Cause, like, if you're doing well, the company wants to put great people on great problems. You know what I mean? And, like, I guarantee you, you know, while it might feel risky and scary, like, if you're doing well and you're the one saying, "Hey, there's something else that's better," like, I guarantee you they have another place that they can go put you, or you can even suggest as part of that, "I, I think this is more valuable. Why don't I go figure out this thing?" So I felt like getting through there, uh, was there. My first time becoming a manager, um, I think a lot of that was probably building a network of people. I, I'm not, like, the biggest networker. [laughs] Um, but I felt like I definitely tried to, in my early career, get to know different managers across Microsoft, and I have always been excited about learning new things. So 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. And a part of that was, like, I always wanted to learn and to push myself to think about, like, "What is a new thing I can learn?" Like, I remember being on IE for like four years, and I was like, "Great. I now know security. I know now, like, browser standards. I know the community. I know all these different things," like I shipped some cool features. "I wanna go learn something new. I wanna go learn how to do a V0," you know? Like, uh, and so I went to the OneDrive team, and back then it was called, like, Windows Files, and that was just an internal name, and we had no idea what it was. And we're like, "Maybe people wanna store files in the cloud. I don't know. What's a great place for them to go upload them?" And, like, that became, like, OneDrive, and I was there till the first, like, few million users. We bought this company FolderShare that I led afterward, the sync engine, and, like, uh, sync story for. We were competing with Dropbox and, you know, eventually Box and, like, you know, Google Drive eventually came along there. And so I think that's something I would definitely give people advice. Um, I find some people really tie their identity around working in a specific area, and if that's really important to you, that's great. You can become an expert there. But I feel like it eventually kind of becomes... It, it is limiting, right? Because, like, you're like, "Oh, I only do security," or, "I only do developer tools," or, "I only do cloud products," or whatever else. I would challenge a lot of people to be like, "Hey, your skills are more general than you think," and, like, get over that fear to, like, try something new because a- you can always bring... I try to look at every new job, like when I went to GitHub or when I went to Vanta or anywhere else or even transferred within Microsoft, around, like, what can I bring that's, like, 70% of what I know or skills I'm bringing, and there's a 30% that's like, I'm gonna learn. And it's like there's a bit of risk and fear with that, but I think, like, taking that plunge will, like, help you just grow so much more versus just kind of it's easy to get comfortable, you know, and stay in that same team. And I've got friends that are successful doing that, that have been working the same product for 20 years, you know? But it's not what excites me. Um, and I think it, it kind of limits your growth potential. So I think that would be the big thing for people. It's like think about, like, where you go, when's the right time for you to go move, what you can learn out of that new opportunity while still b- bringing, bringing a fair amount of skills so you can, like, hit the ground running. Um, I think moving through, like you said, to, like, VP and things like that, uh, a lot of that is probably better understanding of the business context and how to work with go-to-market, kinda getting out of a bit of the feature factory and just like, "Customers need this. How do I build something great for customers?" But also taking real accountability for, like, what does that mean end to end? Like, what is the messaging we're gonna go use? What is that onboarding experience? How is, uh, AE gonna be talking to a customer? Which customers should they be qualifying? Which ones should they be disqualifying, right? Like, how is an SE gonna come in and do a trial? Once we sell the product, what does implementation look like? Where is the product picking up and helping people along the way? Where should we go do that? How do we think about pricing and packaging? Is now the time to change that? How should we be growing revenue? I think PMs overall wanna make customers happy, and that's definitely what, like, drives me fundamentally. Uh, but there's a negative side where they also just wanna give away everything for free. [laughs] And it's like we do need the business to make money, so, like, thinking about, okay, great, what is that line, you know, um, where we need to be charging for this, how much, how... You know, how do you clearly articulate that value to a customer and that pain point? And so I, I look at it as really end-to-end business ownership is really what I think helps you kinda get through that GPM thing into director, senior director, and VP is really, like, owning that.

    9. AGAakash Gupta30:45

       Today's episode is brought to you by Maven. The problem with most courses online, like Udemy, is there's no live component, and the instructors aren't experts in their fields. They're professors.At Maven, you get direct live access to experts and operators from the world's best tech companies. You can't get that access anywhere else, in any university, and you usually can't find them on YouTube either. I've featured so many of Maven's experts in the newsletter and podcast for that reason. To help you out, I've put together a collection of courses I recommend at maven.com/x/aakash. This includes courses like AI Prototyping for PMs, Product Sense for PMs, and getting an AI PM certification. Visit it now at M-A-V-E-N.com/x/A-A-K-A-S-H.

    10. JEJeremy Epling31:33

        And then I think another part of it is around communication, so understanding who the audience is and being able to pretty, like, real-time adapt. Like, you know, when I would go into a meeting, like the few that I had with, like, Satya, or I remember doing a big demo with Nat that we did for Bill Gates, um, right after the GitHub acquisition, and he was like, "Great, I spent $8 billion on this, you know, what did I get?" kind of thing. And it was, like, kind of joking, but, like, also kind of serious of, like, going through it, 'cause he wasn't as hands-on. Satya was there, and it was, like, a two-hour thing of me, like, going through GitHub and explaining it and showing him Git and developer workflows and how it all works, and Nat was, like, outlining the strategy for all those different pieces. And, um, I think, you know, the way I would talk to him would be different than how I would be talking to, like, Satya versus be very different how I talk to my engineering manager or the engineering lead or the marketing team. And I think that's something I still, like, work on and grow on, but I think knowing the right message for the right people, it's easy to overshare and to bring people in all the things that excite you and, like, all of your technical deep knowledge and show it off and how much you care about the product. But, you know, a sales AE is just trying to figure out the value statement to help them, like, land the next deal, and you'll kind of overwhelm them or, like, turn them off. So I think understanding that from, like, a management perspective, like, hey, if you're an ICPM or a earlier career PM or whatever and you're working with a VP, like, what context do they need to make the decisions they need to make, and how do you serve that up on a perfect platter, where you're like, "Here are the three inputs you should consider, and here's my recommendation." Not just, like, dumping it on them to go make the decision, but, like, "And I think we should go do this," and having the right level of conviction around what we should go do, but also being open to feedback. And I think that's the key skill to learn to, like, really transform from that kind of, like, having big impact at staff and principal, even if you're moving up the IC track or thinking about director, senior director, VP.

11. 33:23 – 37:27

    Senior leadership “first team” and the trap of staying too long at BigCo

    1. AGAakash Gupta33:23

       A lot of those lessons really resonate. So the last time we filmed on this set, we had another one of the heads of products of a unicorn company, Brad Schaefer, and I wanna just draw some parallels between his story and yours. I think one of the things you mentioned is speaking up when you should cut your own area. [chuckles]

    2. JEJeremy Epling33:38

       Yeah.

    3. AGAakash Gupta33:38

       This is one of those lessons I maybe didn't learn early enough. I look back at some of my career, like, I was a director of product at a firm, and I feel like I should've done that probably. [chuckles] I was leading, like, 30 engineers at one point, and, like, we, uh, there were times when I was like, "Yeah, we probably could've just put, like, 15 of these somewhere else." And so learning that early in your career, I think, huge, huge lesson for people. I think a second thing it sounds like to me is, like, you were spending, like, four years to get really good in an area, which is, like, enough time to get good in an area, but then you didn't let yourself stagnate, right? You're moving on to new products, new areas, so I think that's really important. And then the final step, which both he emphasized and you emphasized, is moving beyond product, right? At those-

    4. JEJeremy Epling34:17

       Yeah

    5. AGAakash Gupta34:17

       ... final levels, it's like, how do you have a broader impact? Your main team isn't really your product team. It's the leadership team.

    6. JEJeremy Epling34:23

       Yeah. Yeah, and I think that's really true. We use this concept at Vanta that we call, like, our first team, and, like, I think of my first team as actually the C-team suite. So it's like, as much as, like, I am the leader for product engineering and design and, like, all my direct reports, and we have an EPD, we call it engineer product design, like, LT. Like, my first team is Stevie, my CRO partner, David, our CFO, Ari, who's the head of, like, legal and people, and, like, Christina, CEO. So it really is that cross-functional business context that is, like, my first team, because it's also the easiest to kind of, like, fall back into your hole. Like, where is my happy place, and, like, where do I have the most knowledge and experience? It's just, like, building great products. But that's not gonna help the business succeed, 'cause you c- you can have, and there have been plenty of products that have been better and still lost. [chuckles] So you really need to think across that whole thing of, like, the marketing, the messaging, and expanding that breadth. I mean, I think of going back to Microsoft, while I did change teams a bunch, I would say one of the mistakes I made from my perspective was just not leaving Microsoft early enough. I think it ended up working out well with, like, GitHub and everything and kinda going there where it was, like, close but not too that far. I think as much as I changed teams internally, I, I had a bit of fear, um, around just, like, it's so comfortable. You know, you get, you get tied into these systems, and I m- I, I hear the same thing from friends that are still there or at Google or at Meta, you know, or any of these larger companies. I think it's, like, you know the system, you know the people, they know you. They build these great HR systems that are, like, you know, like MMO RPGs, where there's, like, twice the amount of levels and you're slowly moving up and you're always just about to get the next promotion. And, um, it just becomes very comfortable. And I, I guess that would be my challenge to most people, even if you are switching at these big companies and not. Like, if you're comfortable, that should be some level of a warning sign to you that, like, you have now learned everything you need to go learn. I would say you don't wanna leave too early. I feel like two years is a minimum to do anything. I prefer people to be there three or four. But I would say when you get to that three or four, you sh- should be thinking about, do you wanna switch within your company, or do you wanna go to a different one or not? Or maybe you just have a crazy trajectory at your current company, so you are just, like, constantly being challenged and learn 'cause they're going through hyper-growth. Like, we're definitely feeling that at Vanta. Like, we are hiring so much all the time and growing so quickly that, like, everybody's job is changing, it feels like, every couple months. Um, so, like, that's exciting too. But I think, like, challenging yourself on that fear, I know it was, like, a trap that I felt like I fell into, and I felt like I would've learned more quickly if I would've done that. But I think the problem is if you stay somewhere less than two years, um, often you don't see the impact of your decisions, especially as a product person. So, like, you think you did a great job, but you're not around to, like, really take the hard knocks, 'cause, like, you'll make bad decisions. Like, I still will make bad decisions, you know what I mean? And I want to feel the impact of those so I can really learn the lesson and move forward and, like, go from it versus, like, make a bunch of decisions, then I'm off to the other place making it, and you're not really understanding how to build longevity and the impact of, like, a successful business. You kinda become like a mercenary, you know? [chuckles]

12. 37:27 – 41:47

    What PMs should learn from GitHub: developer workflows, technical fluency, and outcome framing

    1. AGAakash Gupta37:27

       100%.So GitHub is so cool. That's where you went after Microsoft. And before we even talk about life at GitHub, what do PMs need to know about GitHub? [chuckles]

    2. JEJeremy Epling37:39

       Yeah. I mean, I think for me, like, uh, for GitHub, I think there's a bunch of interesting tools they're doing to make it easier to code. As much as I love all the AI coding tools, I still feel like people should learn how to code. Maybe five or six years I'll feel different and you shouldn't, but I still feel like they don't get you far enough, you know what I mean? To really be able to do it. It's great accelerant and can help on specific things, but there's still mistakes that are made. So I think people understanding the GitHub workflow is really important. Being able to work closely with your engineering team to know, like, what they're dealing with on a daily basis of, like, pull requests, code changes, how hard it is to make a code change, getting more into architecture. Like, I come from a more technical background. Not every PM I hire comes from that, but I do think there's kind of a superpower that comes. Like, there are times when you need to call BS on, like, engineering of, like, "Can't we go faster here or not?" And be able to actually understand what they're talking about, like why this schema change is really hard or why this performance issue exists, and then know which ones are ones you probably should push harder on. So 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, the high-level mechanisms and systems, because there's still a lot of, like, great PM platform roles. And then being able to have that deeper relationship with engineering where they can trust you and you can trust them because you both understand each other's job. Like, I encourage my engineering managers, I feel like should be able to talk to their team almost as well as the PM of, like, what's the vision, why we're doing it, doing that. Because, like, they're having one-on-ones with, like, eight to 12 engineers, like, every week, you know what I mean? And working with them and keeping them motivated and focused, that shouldn't all just fall on the PM. And then the PM needs to understand how hard it is to engineer and, like, run a product and that, like, these services are alive things and there's, you know, keep the lights on costs and things like that, and fundamentals we need to exist in. And like, "Oh, you wanna move faster?" I think one of the things I encourage the engineering team to go do a lot that I think helps with this translation is always talking in customer outcomes. So I think, you know, we don't wanna say, like, "We wanna go re-architect this." And it's like, "Well, why do you wanna re-architect? There's a reason." And it's like, "Oh, because, like, we see tons of bugs." And it's like, "Okay, great. So we wanna improve quality," and we, like, that's the big message. Like, we wanna improve quality for these customers. You know, we can look at this data, we can see SLAs we're missing, or we can see that, like, people are struggling and integrations aren't connecting as often as we want or something like that. Or they're like, "Hey, I wanna make build times faster." And I think a lot of PMs will be like, "Well, why are we doing this?" And it's like, "I wanna go ship software faster. I want to increase our velocity," and, you know, I'm sitting around twiddling my thumbs if the build takes five or 10 minutes versus if it takes seconds, you know? And, like, I can build that inner loop even faster. As an engineer, I can write more code. So I think 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? 'Cause it probably always is rooted in a customer benefit, and you can help, you know, help show that to the whole organization and maybe actually should be doing more work there. Not saying that's always the case, but sometimes the core thing isn't shipping more features. It's actually just, like, making the current thing better. And I think in the world of AI too, it's just really different. Like, it's very alive. Like, I found the AI products that we ship, like, staying on top of precision and accuracy, understanding what, what quality means for your AI stuff, especially as the models are evolving and changing and you're getting new types of customer input, like, it's very different. And, like, there's a lot more of kinda keep the lights on, keep the quality there, and improve the quality that isn't just shipping new features and customers expect. 'Cause I'm guessing you're probably like me. You've probably also used a lot of AI products that were, like, 80 or 90% hype. [chuckles]

    3. AGAakash Gupta41:26

       Yeah.

    4. JEJeremy Epling41:26

       You get in there and you're like, "This thing doesn't actually work." Um, and so that's something that I really focus on our team, is making sure we can, like, back up those things. And I think PMs can be great for helping engineering translate the why behind what they're doing, because there usually is always a really great reason and a customer benefit. They just might not naturally talk about it that way first.

    5. AGAakash Gupta41:45

       That's the newsletter that comes out today.

    6. JEJeremy Epling41:47

       Yeah.

13. 41:47 – 51:49

    VP of Product reality: always-on accountability, GTM pull, and staying close to the product

    1. AGAakash Gupta41:47

       So many AI products are hype. Here's how not to be. So you read my mind on that one. So you were a VP of product at GitHub.

    2. JEJeremy Epling41:55

       Yeah.

    3. AGAakash Gupta41:55

       And I think a lot of people, very few people reach the VP, let alone at a really big billion-dollar company. But I think people have a lot of misconceptions about what that role is really like. [chuckles] What is it like, you know? How are you... We, we talked about, like, you need to make impact outside of product-

    4. JEJeremy Epling42:13

       Yeah

    5. AGAakash Gupta42:13

       ... for instance. Like, how are you making that impact? You know, how are you spending your time? And at least for me, what I found is the VP role, a big, big difference is that you're kind of 24/7 on, [chuckles] right?

    6. JEJeremy Epling42:24

       Yeah.

    7. AGAakash Gupta42:24

       It's like if the CRO messages me at 10:00 on a Saturday, I will be on with him for another hour, you know, just back and forth.

    8. JEJeremy Epling42:31

       Yeah.

    9. AGAakash Gupta42:31

       So that's how I experienced the role. How did you experience the role?

    10. JEJeremy Epling42:34

        Yeah. I would say the kind of being always on, being the kind of, like, face of the company and accountable for the business becomes, like, very acute, like, at the VP level at, like, most places. Um, so hey, there's an incident, you need to get on and go deal with it. And, like, you, the buck kind of stops with you from, like, the C team. 'Cause sometimes, some companies, and I think GitHub was more this way, like Nat when he was CEO would have relationships with the ICs. I think Thomas kind of does the same thing in there, but you can only know so many people. So I feel like a lot of their direct line into, like, "Hey, I wanna know what's going on in this area," becomes that VP, and a lot of the time it becomes the VP of product, you know, that's there. Sometimes it's engineering, but if it's more technical or quality-based, it'll usually be engineering, but a lot of times it'll still just come to PM first. I think that's it. I think the business side, you spend a lot more time, like, I felt like a lot of my day was just talking to our head of SE, like solution engineering, of like what problems are customers dealing with, how, how we're positioning the product, because GitHub was a more technical sale. AEs did a good amount of, like, setting up the value prop in the high level, but it really, I think a lot of it, the winning the deal fell on the SEs. So we spent a lot of time and were really close to the SE team. So I think at VP I spent more time on that, more time on, like, pricing and packaging and making sure our billing systems were there. We were going through this transformation at GitHub, uh, for usage-based billing, which we had never had before. We had just been seat-based licenses, and, like, when you buy GitHub Actions hosted runners or GitHub Packages or Container Registry or anything, you're paying per megabyte, transfer costs, you know, paying for minutes of compute down to seconds, maybe milliseconds. Don't know if they got to that or not after I left. Um, but yeah. And so I think the way you think about that is, like, very different. How do we pitch that? How do we talk to the value for customers? Spending more time on probably competition at the business level, where it's like, okay, great, you know, a specific area. Who are the other CI/CD providers or package management providers or security providers in the area, and what are they doing? How are we talking about that value?So I feel like a lot of those, like you kind of get pulled a little bit further away from the product. I think the failure mode is to get fully pulled away from the product. [laughs] And so I, every day, am like using the product and going through like basic co- like workflows and like, you know, look at our features. I still comment on like Figma files and try to set a culture where like that's okay and not scary. [laughs]

    11. AGAakash Gupta44:55

        Mm-hmm.

    12. JEJeremy Epling44:56

        You know what I mean? Where it's like, hey, you know, sometimes I'll come in and have like a stronger opinion, but a lot of times it's more just like I wanna make sure I'm connected to like what we're building, 'cause I feel like if you lose that, um, then I feel like you just become this like middle management layer that just like is not rewarding at all to me and I feel like kind of like soul-sucking. Um, and so I think staying close to the product, but also understanding this like larger business accountability, um, and figuring out how do you message to like the CEO and the C team, which is pretty different, especially at like the size of GitHub. Like, you know, they're like well over like a billion in revenue at this point. Like lots of different products, a lot of different things going on, a lot of big partnerships that are happening. And like when I'm talking to like Nat, what are the like two or three things he needs to know, and I need to go talk to him in the minimal context I can give him so he can make a decision and like move on from my area. And what's the stream of updates I can give him that feel right so he just always has confidence in my area? 'Cause I think that's another one. Like I, I've fallen into this trap before too, where I get like so excited about my area and I'm like focusing down deep on it and everything, and I forget to kind of like communicate out what's going on, 'cause it kind of feels like, can feel like BS work and like not valuable, and like-

    13. AGAakash Gupta46:04

        Yeah

    14. JEJeremy Epling46:04

        ... I don't know. I'm, I'm not big on like self-promotion, so like I find it like really weird to like self-promote things. But like if you're not celebrating it and sending that steady stream of communication out, people will start wondering like, "Well, what's this team doing?" You know what I mean? So I think you have to be the voice, the kind of like cheerleader, energizing person for the team, and kind of like play more of that role than you have in the past around like this is the exciting new vision. Get people hyped and excited. I think another big part of it is you just do a lot of like customer roadmap calls. Uh, you know, like I, I don't know, I probably have one, especially at Vanta, but even as at GitHub, like it felt like almost daily. Maybe it probably wasn't daily, but like multiple a week, where it's like big customer wants to go talk about the roadmap. Maybe they wanna dig into something deep. If you're at a really big company and you have like a section of the pie versus now where like all the product is like on my team, and talk about where we're going. I can go deep in certain areas, get them excited about the vision, get direct feedback on things. You know, take that to the team, pull in the right people, um, for those calls. So I think you start spending a lot more time on that as well.

    15. AGAakash Gupta47:07

        Okay. Sounds scary. Sounds like a lot of work. [laughs] Sounds like a lot of messages-

    16. JEJeremy Epling47:14

        Yeah

    17. AGAakash Gupta47:14

        ... and a lot of meetings.

    18. JEJeremy Epling47:16

        Yeah. I mean, I think for me, I am continually trying to do a better job managing my calendar. [laughs] I think it's easy to kind of fall in this trap where like I just look at it and it's like, I don't know, like, you know, it can be like 9 to like 7 and you're just like packed. You know what I mean? And so I think the thing I've learned is like I have to fight that and like record off sections where I can just do IC work. See, something I really value, I think Christina, other founders really value this as well, um, is you're never not an IC. And I think that's when you start to get into what people consider like the bad parts of middle management or general management and things like that, is when you stop owning an actual outcome. So it's like to me, there are still docs that like I write and things I comment on, and like specific issues I want to go drive, or I will go work deeply with the team on this specific new AI feature that we're working on and give them like more detailed, you know, thoughts on, "Hey, I think it should go this way or not," or, "Tell me about this." And I think that's when things get bad, when it feels like you're just a translation layer, you know? And so for me, making sure that you have like a clear set of IC things that you're driving and delivering is what's gonna make the job really exciting and I think make you impactful, especially if you wanna be in a more kind of like founder mode, [laughs] like style startup. Um, and a lot of the Silicon Valley style startups, I think there's very little tolerance for kind of like pure management and just focusing on people and keeping them happy and teams happy and moving along and just delivering. It's like, no, you need to be like a leader and a driver in making decisions. Um.

    19. AGAakash Gupta48:51

        Yeah. I also experienced that as a trend, though. So I first made director in, I guess, 2014. And I was kind of at the director level for six or seven years. I remember when I first started, that was more the expectation. Like, I wasn't gonna write docs-

    20. JEJeremy Epling49:05

        Yeah

    21. AGAakash Gupta49:05

        ... or anything like that, but by the end of it, it was like, yes, you need to be an IC and you need to... Claire Vo, she's a CPTO, right?

    22. JEJeremy Epling49:12

        Yeah.

    23. AGAakash Gupta49:12

        So similar as you. She says she still PMs like one feature [laughs] a quarter, you know? It's like-

    24. JEJeremy Epling49:17

        Yeah

    25. AGAakash Gupta49:17

        ... you so need to be close to the bare metal.

    26. JEJeremy Epling49:19

        Yeah. I mean, I'm 100% aligned with that. Like even recently, Christina, our like CEO founder, like there was an area she was really passionate about and I was just like, "Do you just wanna do this?" And she's like, "Yeah, of course." Like, [laughs] so she like, she wrote the PRD. She worked with the IC engineers and designers, and it was like a small little feature, but it was like impactful and actually ended up having like really good metrics results at the end of it. I guess as you would expect.

    27. AGAakash Gupta49:40

        Expect.

    28. JEJeremy Epling49:40

        Like she's super talented.

    29. AGAakash Gupta49:42

        Yeah.

    30. JEJeremy Epling49:42

        Um, but yeah. And I, I do the same thing. I think that it's hard to tell people how to do a great job if you don't know what that job is and how to go do it. If you're not enough in the details to actually give them practical advice on how to grow and like why this decision makes sense, why this one doesn't. Like, why should the design be focused on this versus that? Should we move this button over here? Or like I go to the page and it's weird. We have like three different status places that are all like disconnected. Can we like pull that together and focus the customer? And like, you know, things I'll go when I dig into designs is like what's the job to be done on this page and this flow? And like how can we cut, cut, cut? Like some of the ways I think design can be the most impactful is as an editor, and PMs as well, which is around creating that focus. What can we cut off to really make sure the thing people are coming to to do most of the time is really the focus and the thing that we're celebrating? Um-Yeah, I think on the AI side, like, there's just so many different things too where I think there's great things about chat. There's cases where it's, like, not the interface that I want. Um, and I think it's really easy to get pulled into these situations where you're have a solution looking for a problem. And, like, the thing that I always talk to, it's like, "What do we wanna go do for..." You know, we do security and compliance software. We think about, like, vendor risk management is a big thing for us. So, you're, like, onboarding all these vendors. You're doing procurement. You need to go do security reviews of them. And, like, the thing that gets me excited is not that, like, I can go chat with an agent about it and tell it to go do things. To me, the best experience is, like, I don't do anything. You know what I mean? Like, it just comes to me and says, "I've done the security review for you. Here are the findings contextualized to your program. What do you wanna go do about these next?" And not that it's just, like, helping with the little tasks and I'm programming it. So, I think keep in mind, like, what is that big goal that you're going after? What's that root customer problem you're solving? And making sure you're always focused on that, I think, is the thing that PMs can go do and, like, the superpower they bring is, like, that focus on, like, the core sets of customer problems and how that's gonna help the business, like, drive revenue or usage or, like, whatever the outcome you're trying to drive is.

14. 51:49 – 57:41

    Becoming Vanta’s CPO: finding the right growth stage and culture fit

    1. AGAakash Gupta51:49

       So, now we've alluded to you're CPO at Vanta. A lot of people wanna get a role like that. Vanta's one of the hottest companies. It's growing really fast. Talk to us a little bit about how you got that role.

    2. JEJeremy Epling52:01

       Yeah. Uh, it was an interesting process. I, uh, I think for me, I had been at GitHub, like, three or so years. I was getting to that four-year mark. It's kind of like, as I said earlier, like, my itch time when I'm like, "Okay, I felt like I understand these businesses that I built there. I feel like they're good. What's something next?" And GitHub was getting just a lot bigger, and I think the thing I've learned about myself is, like, that early scaling phase is, like, what I love. And so I knew for me, I didn't want to do the, like, Series A seed wander the wilderness. Like, I knew that about myself. Where I was like, life stage, I've got, like, three young kids, everything like that. Like, wasn't, like, wasn't ready for, like, that level of commitment, you know what I mean? To something like that where I'm like, I feel like it has to be your, like, entire life and focus, um, to make it really successful. I think I was also like, if I'm gonna go that early, I want it to be my thing, so I probably just want to found again. Um, but, uh, yeah. So, I was trying to find what it was right, and I was like, "Okay, BC stage company feels great. I've done this kind of platforming thing at multiple places. What's a company that wants to go do that?" And something where I felt like I could bring some of the knowledge I either had from, you know, OneDrive or consumer products or developer products. And yeah, just started meeting with founders. I mean, I think, um, for roles like that, you know, there's not usually as much outbound as you do. It's like you'll get... You'll talk to different people, networking. Like, I got to know some venture capitalists and different firms that I'd known and worked with in the past. They were telling me about different jobs that were there. Um, different recruiting firms were kind of, like, reaching out, and I've let a couple of them know, like, "Hey, I'm looking for something. Not exactly sure what it is. It probably has this kind of shape to it, though." And then, uh, conversations started to happen. Um, and yeah, I met with, uh, Christina, like, uh, I don't know, maybe I'd been looking for, like, six months or so. It could've been a little bit longer. I remember meeting with her and just having, like, a really strong connection. And I was like, "Oh, wow, I think this could, like, really work." Um, but at the same time, I wasn't sure if I really wanted to leave, like, GitHub yet, but I felt like I did. And, um, a reorg happened there. My team got even bigger, and then I was like, "You know what? I, I don't wanna leave." Like, we had two good conversations, and I was like, "I'm happy here. This is all great." Um, and then I think it was maybe six months after that, I think she, she reached out back to me, or one of the recruiters did, and was like, "Hey, we're still interested. Would you be up for talking again?" And I realized, like, that completely didn't make me happier. Like, I thought, like, getting the bigger scope and everything would make me happier, and I felt like it was just pushing me into more of this general manager side of just kind of, like, managing this really large scope and not as being hands-on, and just didn't excite me. Like, I felt like I wanted to do that, like, build it, scale it again, and, like, that's what just, like, really gets my juices flowing. Um, and Christina, uh, had reached out again then. I was like, "Yes," like, "Let's," like, "Let's talk more." And yeah, it was an interesting process. It was, I don't know, like, nine weeks we probably went back and forth. I was traveling a lot for GitHub, so I remember taking a call from, like, Paris [chuckles] 'cause we had, like, a GitHub conference in there with her doing it. Um, got to meet a bunch of the C team as part of that process. Had a lot of conversations with her. I mean, I, I kinda look at these as kind of, like, dating maybe. Like, just as much as, like, can you do the skills, it's like, will you fit in the culture, and d-do you think our working relationship would be great? And there's other founders I met with where I was like, "Oh, I love the company and the technology. I think my skills fit," but, like, we just didn't click for whatever reason, you know? And either they weren't interested in me or I wasn't interested in them because, like, it just didn't get to that point. Um, and yeah, I felt like it was great with her and got to meet some ICs for the team, which I thought was really great. One of the huge, like, kudos I can give her in the entire process is I had no surprises when I started this job. She's like, "I am going to tell you all the good and all the bad. Like, here's the team. Here's what's working. Here's what's not working. Let's have you work with some ICs on the team." So, I actually did a couple calls with ICs. I got to review a bunch of their specs. I got to go meet people from go-to-market, and it was like, "Here's one of our sales leaders. Here's how they pitch the product, and, like, ask them any questions you have." And I thought that just built so much trust with me and really showed the type of culture she wanted to go build at Vanta. She also was, like, very big on, like, wanting to get into the details, but not in a controlling, micromanaging way. But like, hey, if there's a problem, she wants to get in. She knows the business really well and, like, can ask hard questions and can go push. She doesn't want hierarchy boundaries, which is something I don't like either. Like, I wanna be able to go work with an IC designer or IC engineer if I need to. Or just, I remember times even, like, at GitHub, which was, like, even larger, Nat would ping me about something, and I was like, "I don't know, just, like, go talk to, like, Josh about this." Like, [laughs] you know what I mean? And like, so I like that type of culture, and I felt like we were really building that there. Really loved, like, the leaders and, like, revenue and everything, and I think I've seenAnd talk to other people where, like, the C team doesn't quite mesh. You know, at a company, you can tell they're not like... It's not like everybody has to be friends, but I think we, one of the nice things about Vanta is, like, we're all just, like, we want to achieve the same thing, everyone's good at their job, and we're all just, like, kind of friends, which is, like, really nice. Like, there's this magical culture that I think Christina has built around it being kind and, like, welcoming, but also, like, focused. Like, we need to deliver. There's always urgency, but there's also clarity to go along with that so it doesn't feel like chaos. There are times it's hard 'cause, like, I don't know, like, just on my team, I think we hired, like, 40 people in the last quarter, and-

    3. AGAakash Gupta57:13

       Whoa

    4. JEJeremy Epling57:13

       ... and we're planning to hire 40 people every quarter kind of as revenue keeps growing the way it is, so it's like it's growing very quickly. So, like, there is some chaos, you know what I mean, with that. Um, but I think there's this magical thing about the culture around if you can find a place where you actually like the people you're working with, and they're good, and you have a good business, [chuckles] like, I find that was very hard to go find out of every startup I talked to, and Vanta has it and has, like, really proven that to me over since I've been here.

15. 57:41 – 1:03:46

    Vanta’s growth engines: automating compliance into a trust management platform

    1. AGAakash Gupta57:41

       So most people have probably heard, you know, I think Vanta's been advertising on Lenny's for years now.

    2. JEJeremy Epling57:46

       [chuckles] Yeah.

    3. AGAakash Gupta57:46

       They've heard, like, the basic pitch, right?

    4. JEJeremy Epling57:48

       Yeah.

    5. AGAakash Gupta57:48

       We do s- SOC 2 compliance, security. We get you ready for the enterprise. I think what they may not know is what are the engines that have been driving that growth, that they could hire a VP of product from GitHub, and that you're hiring 40 people a quarter? What is really-

    6. JEJeremy Epling58:02

       Yeah

    7. AGAakash Gupta58:02

       ... the secret sauce behind Vanta's success?

    8. JEJeremy Epling58:05

       Yeah. I mean, I think we have a couple different products. So I think there's the one that probably a lot of people see through Lenny's or if you're in the startup community, which is, hey, you're a startup, and you have a prospect that came to you. They love your awesome new product that you've built, but they don't know if they can trust your security practices. So they're asking you, "Hey, do you have SOC 2? Do you have ISO? Do you have some certification to let us know, like, you're gonna take care of our data?" Because so many breaches have happened because of not the company having a problem, but one of their vendors having an issue. And so I think that was the magical thing Christina created kind of from the beginning was, hey, 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?" And come in, install Vanta, we'll connect into all your systems, and we'll help you burn down a list that will help you build a really solid security program that will help you pass a successful audit, but guide you along the way, because startup founders, they're not caring about security or compliance probably. [chuckles] They probably don't have experience in it or, like, CTOs either, so it's, like, this very weird process, and they're not familiar with it. They're probably not even ready to hire someone that just does it yet, right? They need to be focused on product market fit. [chuckles] And so our goal is, like, let us come help you. And then we have, like, a very different conversation with, like, large customers. You know what I mean? Where it's like they have CISOs, they have big security teams. What they're looking for is to drive efficiency. And when you think about Vanta, the thing we talk to them about is, like, hey, we're a trust management platform, and it has these eight pillars, and there's compliance, and there's audit. We talked a little bit earlier about, like, vendor risk management is a big thing. Customer trust is a big one with, like, trust centers. Like, you wanna go sell your product, you're gonna get a bunch of security questions. How do we leverage AI to go ahead and automate those and do questionnaire automation and make it so people can just ask questions and get answers and not bother the security team, the engineering team, everything else, just, like, get them the accurate, quick information there? And so those have been, like, new product lines that we've built over the last couple years to continue to grow the breadth of our offering. Um, and I think the really cool thing about it, especially for, like, PMs that are thinking about this, is the security team's never actually had a feedback loop. Like, I think we kind of, like, think about, like, product development, and we're like, "Okay, we're gonna go build it," and we go ship it to customers, and we hear from them, and we have all these signals that come back, and then we use that to go, like, make a better product. A lot of time, the security team doesn't have that, and I think that's what we've created with this customer trust and vendor side. You have this network of people selling software and buying software, and we know the questions people or the buyers are asking, and we can tell you, actually, these parts of your program are having a huge revenue impact, like these certifications, or we're mining gong calls and pulling stuff out of Salesforce and, like, HubSpot and saying, like, people are asking for these certifications or these type of security commitments and red lines or contracts or things like that. And then that can drive as your feedback in how you make your program better, and we can help guide you and automate that, and then we help you show that off, so now you get fewer questions like that and can build that. So I think building that product development life cycle has been, like, the big vision of where we've been going forward or just looking at expanding the breadth of the platform to handle more different pieces of what those teams do, whether it be going deeper into risk management, vendors, you know, questionnaire automation, going deeper into personnel monitoring, like we provide security awareness trainings [chuckles] and, like, you know, helping you kind of go through each of those pieces.

    9. AGAakash Gupta1:01:25

       Okay. So you guys have really become, like, a full cybersecurity platform for CISOs, and it's not just that s- PLG side of the story that people might have heard about. Is one or the other side, the PLG or the enterprise side, driving more of the growth these days?

    10. JEJeremy Epling1:01:42

        Yeah. I would say from, um... Obviously, the, like, uh, upmarket customers drive, like, much bigger deals, as you would imagine. But I would still say fundamentally our business is primarily a downmarket business, and we never wanna give that up. Like, I would say our first passion is, like, helping startups build strong security programs that then help them go win their customers. And so that will never be a lack of focus. We're always doing work of, like, hey, how can we tweak this and make it even better? How can we help people scope their controls and do, like, less work but still get better security outcomes? So I think that's still a big part of the business. Um, one of the unique things about Vanta is, and, like, we're kind of, we're changing this over time, but we still primarily do direct sales, even to, like, small companies. And I think part of that is because we have such an uninformed buyer. Like, when you think about, you know, when I was at GitHub, it's like-One, I guess every developer knows what GitHub is, but like the second you learn code, you probably learn Git and source control pretty early on, so you like roughly know what you're buying and doing. If you're a startup founder and someone tells you to go get SOC 2, like you, you have no idea what to go do. [chuckles] You know what I mean? So you have a very uninformed buyer. So I think that's been a case where direct sales has been really helpful, 'cause we can talk about our value, what this process looks like, how we're helping you with everything. We're gonna connect you with a pen tester, and we're gonna go ahead and make sure audit is in there, and like all the different pieces help you scope that down to like, so you're just doing the work that you need that matches your business to have a great security foundation. So yeah. So I think for us, the down market is a big focus, up market's a big focus, um, and then trying to continue to add kinda new products to kinda diversify like the line, and from the business side, kind of add more new revenue streams. You know, I think like a lot of product people probably think about, I kinda think of it as, you know, we have like different horizons. Like, we have products that are maturing this year, and we're expecting to like drive a lot of revenue and a lot of usage, a lot of excitement. We have stuff we're incubating this year that we think will go big next year, and then we have a lot of kind of like little ideas that we're starting that are maybe three years out or more. Um.

16. 1:03:46 – 1:11:10

    How Vanta builds: design-forward craft, weekly product deep dives, platform foundations, AI adoption

    1. AGAakash Gupta1:03:46

       So you guys, I think you probably are proud of winning Most Innovative Security Company last year, so a lot of that has to go to-

    2. JEJeremy Epling1:03:52

       Yeah

    3. AGAakash Gupta1:03:52

       ... the product people. You and Christina probably at the top of that. What are the unique things about how you guys build product?

    4. JEJeremy Epling1:04:00

       Yeah. I mean, I think that in my opinion, I've tried not to throw too much shade here, I'd say [chuckles] like most security products have a pretty terrible customer experience. [chuckles] You know, when I talk to most CISOs, I feel like they agree. They're like, "Yeah, we just kind of like put up with it," you know? Because like the data is at least good. Um, and I think that's an area where we've differentiated from day one, and I would say when I came in, that's something that I feel like I like really supercharged. Um, you know, we had a design team, but I brought in Deb. She's like an amazing design leader. Um, and we've really invested in building up and giving design a much stronger, um, place at the table. We've really focused on PM, really thinking about like what is the value message? What is the customer problem we're trying to go solve? Still work on the UX side of it and partner deeply with design. Um, I run, you know, I think at a lot of other companies they're called product reviews. I call them like deep dives, 'cause I don't want it to feel like, like a review, like you're getting a grade. [chuckles] But, um, every week I'm in at least one of those, where like I am seeing demos from the team, or we're walking through Figma files. You know, I, um... Or it could be like live demos. So to me, being like really hands-on and giving that specific feedback is really important. Like, I wanna feel the customer experience because it gives me confidence we're building the right thing, and I know how to go talk about it and like the roadmap and everything. But maybe it's back to this kind of like founder mode thing, but it's, you know, being hands-on in the right ways. You know, there are certain areas where I'm like, "Oh, yeah, this project is going great. It's on the rails. It's there. I can pull out." Another one's early, or I have a question, or I'm like starting to like look through the designs and I'm like, "Hmm, I have some questions," and like we can go set up a meeting, you know, or jump onto one of these kind of deep dive meetings that we kinda have every week and like go really deep into like, oh, is the onboarding flow exactly right? You know, to make it so people are like invited into the experience, getting the value. Are we talking about the messaging for the product in this right way and casting the right visions? The sales team know what the key differentiators are of like why they should go sell this and like how we should go market it. So I think a lot of that, getting design more involved, empowering design more, having PMs have broader scopes and thinking more about the business and the end-to-end scenarios and the problems, and are those really coming together. And then really like unleashing engineering just to like build, build, build. Like, we definitely do investments in our platform. I think one of the things we've changed in the last year is getting more focused on building a strong platform. I kind of think of as like we're trying to make this thicker platform horizontal layer with like smaller apps on top of it, so when we wanna ship a feature like, you know, commenting or notifications or any of these types of things, or enhance it, it just kinda gets better everywhere, or it's very little work to kinda to add it to the vendor risk part or to add it to audit or to add it to risk or some of these other verticals we have. So I think that's definitely been a switch for us as well, and we've invested a lot in our engineering foundations. Itch is our head of engineering. She's like an amazing leader and has really built a strong engineering strategy of how, if we wanna ship faster, how do we make our build times better? How do we make our code more clean? How do we improve type checking and like all these different things? How do we get more intentional about like how we're testing our code and doing it quickly? How are we leveraging Cursor or Windsurf or some of these like new editors with built-in AI capabilities to move like even faster? Um.

    5. AGAakash Gupta1:07:15

       Awesome. So if we think about it, you're trying to really embrace all of these AI software out there.

    6. JEJeremy Epling1:07:23

       Yeah.

    7. AGAakash Gupta1:07:23

       I think that's very different from the other companies and leaders sometimes that I talk to. How, as a leadership team, what is your guys' perspective on that? Are you encouraging people basically to always be submitting requests for, "Hey, let's get security clearance for this software so that they can use their software on their own," or are you prescribing different software after you investigate it? How are you handling, like all these new tools every-

    8. JEJeremy Epling1:07:46

       Yeah

    9. AGAakash Gupta1:07:46

       ... three to four months? I think Windsurf is four months old.

    10. JEJeremy Epling1:07:48

        [chuckles]

    11. AGAakash Gupta1:07:48

        You guys are adopting it, so.

    12. JEJeremy Epling1:07:49

        Yeah. Yeah, I mean, I think we encourage people to really try things out. We put a couple guardrails. I would say the biggest guardrail that we put on, especially as a security company, but I feel like the number one question I hear, or as someone who is helping answer questionnaires we can see through our data, is like, "Are you training on our data?" And so we do not do that at Vanta, and whenever we're trying a new tool, we have very strict guidelines. We're like, "Never put customer data into any of these tools that we're trying," especially if they could like train off of it. And some of them, you just pay more and then they don't train on your data, you know, [chuckles] like OpenAI or whoever else. Um, but I think that's like the hard line. But other than that, we're trying to like really experiment. Um, and so we have multiple different teams where people are kind of like running off. Uh, at the all-hands that we have for engineering, we have a whole section on AI every single month that we go through, talking about like macro aware, like what's happening in industry overall. Micro, what are we delivering? What are we trialing? What are we doing? We try to build a strong culture. Like, even we did the v0 thing is something I was really excited about, 'cause, um, I know the Vercel team like fairly well and different people over there, and I was having good experience with it. I remember when I first sent it out, my technical PMs, which we, is maybe like a third of the team, instantly started running with it, and everyone else was like, I just noticed low uptake. And I remember talking to them at like our company kickoff, and I was like, "Hey, like why aren't you using this?" And it's like, "I never learned how to code. I know people say this is easy. I tried to kick the tires. It was hard." And so I was like, "You know what? I'm gonna do enablement for this." So like I actually just recorded a Loom fileAnd I went in and I was like, "This is how you do it. This is a Figma frame. Pick this one." And I gave them a V0 template that they could all fork from. And I'm like, "Just fork from this. Here's an example. Here's what I did, how you move things around," and recorded, like, a 20-minute, like, Loom demo. And then, like, now, like, every PM is producing things. Um, you know, for design, we use Figma, so we got Figma AI and are trying to push that, trying to connect that with CodeConnect into Cursor and different pieces. So, I think the big thing is to not be hands-on. You know, you kinda need to set some reasonable security guardrails for us, which is like, don't, never put customer data in these things. Um, but outside of that, I think you should really be open. I think the other thing, too, is having a low tolerance for, like, BS and, like, hype. I feel like especially when I talk to our sales leader, Stevie, she's just like, "Oh my gosh, so many of these tools." Like, I, we do the demo, and then it's just like it falls down. So I would say really do the demo and try to make sure you're getting the value out of them before you, like, sign a contract or go forward, because I feel like a lot of them have a really exciting message, and hopefully they deliver on that eventually. But I haven't seen that always be, like, a one-to-one, and a lot of the time it's like there's a lot of hype, but there's, like, not really that acceleration. But you need to play with it to, like, try. So I, I'm big into, like, all of EPD is fundamentally changing now, and I want us to be on the, like, cutting edge of that. And I think it's an exciting reason to come to Vanta, too. Like, you know, with EPD hiring, like, you know, 40-plus people, like, every quarter. Like, if you're excited by that and you want to go be part of that environment that's trying to rethink how this works, like, you get to work at an amazing company with a crazy growth trajectory. You know, it's building a great product, and you get to be kind of on the cutting edge of, like, how these tools are working. Um, and we have such close relationships with, like, Figma and Vercel and many of these other companies. It's, like, you know, um, very easy for us just to, like, work with them and collaborate and give feedback.

    13. AGAakash Gupta1:11:05

        So we talked a lot about PMs getting oriented towards business outcomes. We illustrated-

    14. JEJeremy Epling1:11:10

        Yeah

17. 1:11:10 – 1:19:23

    Evaluating and leveling PMs: the ‘three Bs,’ ambiguity, and advice for brand-new PMs

    1. AGAakash Gupta1:11:10

       ... how that happened over the course of your career. How do you evaluate PMs at Vanta?

    2. JEJeremy Epling1:11:15

       Yeah. I, um, I think there's a couple key things for me. Um, you know, one of my first managers gave me this framework, and it's not perfect, but, like, I continue to go back to it a lot of thinking about, like, what are the different PM, like, archetypes. And he always referred to as, like, the three Bs of program management. Or he was like big brain, he kinda called it. Like, how good are you at, like, vision and strategy and doing that? Bulldozer, how good are you at just, like, just getting stuff done? Even if there's a wall, you are just gonna, like, plow through it. And then, like, bridge builder. Like, how well are you at connecting with other people, building relationships, building, like, a team, and, like, helping lots of people get together and drive it? So I use... That's not our exact framework that we use internally, but I think it's, like, an easy to kind of, like, remember one. But think about, like, the impact people are having, and then the right level of them being able to do each of those roles. I think as you grow up the ladder, to me, the big thing is, like, it's all about, like, me giving you a more ambiguous problem. Like, I look at that as the difference between, like, what we think of as IC3, 4, 5, 6, all the way up to VPs. It's like, how big of an ambiguous problem can I give you? And then it's a certain stage when you're just finding your own problems and solving them, and I'm never even thinking about it. And so I look at senior PM as kind of when you've established all those baseline skills. If you look at those three Bs, you're kind of doing all of them well. Like, you can drive for results. You know, you can energize the team. You can create clarity. You can get things done. You can, like, work across team. You're doing that. And then when I look at staff and above, that's when I start thinking about specialization, where it's like, what are your superpowers? What are you really great at? And how do we help you do more of that? And then if you wanna go into management, um, it's also a lot of, like, how are you getting the most from your team, but still making sure that the people don't kinda get trapped into this, like, "I'm just a manager," but, like, also what are you delivering? Like, what are you making great about the business and the impact? And so, um, I think evaluating PMs, a lot of that comes down to kind of the what are they doing? What's the business impact that they had? What did they deliver? What are the metrics that they're moving? As much as you can go have those. And in some areas, it's more ambiguous than others, and I'm comfortable with that. I'm very much an art plus science, like, EPD leader. Not, like, everything's 1000000%, like, data-driven or data-informed, but, like, I'm, I'm very comfortable with, like, gut and this feels right in a lot of cases. And then how did you do it? Um, because, you know, if you look at those, like, three Bs, you can be, like, the best bulldozer and everyone hates working with you, and you're like a bull in a china shop. You know what I mean? You destroy your relationships. Or, like, the bridge builder. Everyone loves working with you, but you, like, don't get anything done because you, like, can't, like, drive for the results side. Um, so...

    3. AGAakash Gupta1:13:49

       That in and of itself is a great template, but I wanna ask, if a new PM joined your team with no experience, what is the advice you would give them?

    4. JEJeremy Epling1:13:59

       Yeah. No experience in kind of, like, program management-

    5. AGAakash Gupta1:14:02

       In product management

    6. JEJeremy Epling1:14:02

       ... or product management.

    7. AGAakash Gupta1:14:03

       Yeah.

    8. JEJeremy Epling1:14:03

       Yeah.

    9. AGAakash Gupta1:14:03

       Maybe they were an engineer like you started out as.

    10. JEJeremy Epling1:14:05

        Yeah. Yeah. I would say the biggest thing I would say if you're brand new is-Find the core customer problems that you need to go solve. Like, go talk to the customers, find out where their most acute pain is. Like, what is their daily life? Like, I would almost create a map of saying, like, "This is what their daily job looks like," and, like, how they could use a tool like Vanta to go make it easier. And it's like, "I do these three things, and I feel like these are where I'm, like, wasting all of my time." Like, it feels like I'm doing low-value work, right? Or areas where I want to be spending my time. And then hone in on those problems and figure out, like, how you automate those and make those take no time. Because then you have a clear business ROI for selling your product, and everyone just loves it because you're, like, helping them do the things they hate doing. You know what I mean? And that are repetitive or boring. Like, questionnaire automation's a great one. Like, no security team wants to give out these questionnaires. They're all the same, but they're slightly different. They should be focusing on the big risks for the company and, like, securing the actual, like, foundations of the software that they're building and the company. But instead, they're answering for the three millionth time, like, "Do you train on my data? What is your encryption level? What is this?" And, like, it's all time lost. And that becomes a really easy conversation then when you kind of move up and you're thinking more about, like, the business. And then you can have a conversation around value with whoever the buyer is and be like, "Hey, we're gonna save these people on your team, like, five hours a day doing all this work." Like, I had a customer come to me, I'm asking if I can use this quote more publicly, uh, so I won't say their name, but they were like, literally after Vanta, they're like, he's like, "I could work three-day weeks." Like, [laughs] "It has saved so much time for me." And this is someone that's at the, the higher end. We're like dedicated security professional, not there. But he was like, "You've just cut two days of work out of my life." And he had only been using the product for, like, a couple months. And so I think finding those pain points, mapping out how people are trying to do their job today, where you can make it easier and really delight them. I think another question I like to ask that I think is interesting is tell them to imagine a future that's not just, like, make this thing better, but, like, what is your crazy wave-a-magic-wand future? You know what I mean? Like, what do you wanna completely eliminate? What would be transformative to you? And I think that will help you figure out where you want to go. And then the other conversation of what they're doing today will help you build that map and that roadmap around, "I need to do these things." So I would say getting really good at having conversations with people, understanding their pain, and being able to tie that to, like, a value statement that someone would put, you know, money behind and, like, care about. Um, it's a little bit different if you're in kind of an ads-driven business where, like, they're, you're not, like, selling SaaS-

    11. AGAakash Gupta1:16:41

        Yeah

    12. JEJeremy Epling1:16:41

        ... and all about usage and utilization and things like that. But if you are in SaaS, where you're, like, selling to kind of, like, small businesses or enterprise or anything, I think being able to tie that pain to that ROI, and then that sets the template for your AEs, you know? Um, I would say also, like, get on sales calls. Like, be on there. You should be able to sell the product. And, like, watch what your best AEs do. Like, if you're using Gong like we do, like, you should be watching the calls of your best AEs and figuring out how they could do better and then what you're learning from the customer response. Like, I was in Sydney at our office down there in, like, October, and I sat in on a bunch of our calls, and it was amazing. Like, just learning for me of just even smaller ones, where it was like we were talking to companies that were, like, 10 people or less, like, or five of them. And, like, you know, you have five people, and just, like, sitting there, hearing how we're pitching it, how we can refine it, how I could make that demo better to, like, help make that, like, salient point, like, right there. "Oh, we should tweak this in the product. Oh, my gosh, this does feel painful. They're having this conversation the, like, wrong way, or I wish they were having it this way." And so I think digging into that. So a little bit of, like, early career stuff around identifying customer pain, problems, doing that. And then I think as you go, go more further in your career, really understanding how to get that value messaging in there.

    13. AGAakash Gupta1:17:53

        Couldn't agree more. Jeremy, thank you for doing the pod.

    14. JEJeremy Epling1:17:56

        Yeah. Thanks for having me. This has been a great conversation.

    15. AGAakash Gupta1:17:59

        Hope everyone enjoys it. If people wanna find you online, where can they find you?

    16. JEJeremy Epling1:18:02

        Yeah. Um, I'd say you can find me on LinkedIn and on X as well. Just Jeremy Epling on both of them. Keep it simple. Um, and yeah, I think one of the big things I'd just leave everybody with is if anything here excited you, I would love to chat with you. Uh, we are hiring a lot in product engineering design, but not just there. We're hiring in go-to-market, um, in marketing, and all these different roles, sales. So would love to talk to anybody that gets excited by Vanta, wants to build things in an AI-forward way, wants to really think about how to build awesome products that people love, that are well-crafted and great, and wants to join a business that's showing, just doing tremendously well, so.

    17. AGAakash Gupta1:18:41

        Yeah. There are f- these career-launching companies. For me, it was ThredUp. It was like I joined it at Series C, made it through Series E. Now it's IPO'd. I think those are the type of companies you're looking for at a certain stage of your career, and I think Vanta's a great example of one.

    18. JEJeremy Epling1:18:54

        Yeah, definitely.

    19. AGAakash Gupta1:18:56

        All right. That's it. I really hope you guys enjoyed that episode. It would mean a ton to me and the team if you could please subscribe on YouTube, follow on Apple and Spotify podcasts, and leave a rating and review. Those ratings and reviews really help grow the show and help other people discover the show, and they help fund the production so that we can do bigger and better productions. Can't wait to share the next episode with you. Until then, see you later.

Episode duration: 1:19:37