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

0:00 I would say one of the mistakes I made from my perspective was just not leaving Microsoft early enough. What is really the secret sauce behind Vanta success? 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 I think when you look at new tools coming out whether it be like Lovable or Vzero or Bolt we actually have Vzero licenses for every PM on my team. How did you make those steps up the career ladder? 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. 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 the team I think for more than like 4 years. I want to go learn something new. I want to go learn how to do a v zero. I think for GitHub, they have a bunch of cool tools for PMs to think about, you know, whether that be C-pilot, 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.

1:12 Encouragement for engineers and even for PN when you're talking to engineers is just ask them the why if you don't understand like why do you want to go do this thing? When you're working on Outlook, another billion plus user product. Can you bring us back? What was a day in the life like as a Microsoft PM on Outlook? 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 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.

1:54 Jeremy Eping 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. Oh, thank you for having me. Excited to be here. So, you worked on Internet Explorer when Internet Explorer was cool. Yeah, definitely. in the like early 2000s I was there and got to work on a bunch of really exciting new features which seem kind of 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 want to go with that and like the early days and yeah it was a really exciting time because so much was changing and this is way before Chrome came Firefox was just starting to become a thing out of Mozilla. and yeah, just a ton of competition and really kind of exciting innovation going on on the web. 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 20page PRGs. Is that what life was like for you as a PM? 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.

3:31 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. 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 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. 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 going to continue to increase where PM support more and more engineers is that kind of the have you seen a straight line trend through your career on that?

4:38 Yeah, definitely. I mean I think that's the way it should be going is definitely the way I'm leading our engineering product and design teams. I mean, I think when you look at new tools coming out, whether it be like Lovable or Vzero or Bolt, we actually have Vzero 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 don't 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, 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.

6:00 We're seeing designers even starting to do pull requests. It's something we're talking within our team about how we get more there. so I do think the whole notion of how engineering, product, and design work together is completely changing right now. Yeah, everybody has 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 guard rails 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? Yeah, I think that the more kind of overlap the better in a lot of cases, but I also am very comfortable having teams work differently. Like 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. I do think 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 Verscell, 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 want to get that product in the hands of customers. I want to 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 cuz like I can tell you when I want to move a button from the left side to the right side, I don't want to go have to go describe and chat like go target this thing and please move it over here under this and do that and change the color to that. I kind of just want to click on it and drag it and move it. And so I think we're going to 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 v 0ero or 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 going to 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.

9:28 There's just a huge opportunity like design systems like I just want to 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.

9:56 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, road maps, 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 crossunctional teams, and monitor development progress in one place. It cuts through the maze of disconnected systems that are complicating my life.

10:33 Product teams at OpenAI, Versell, Rex, 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/ a kh. That's linear.app/partners/ akashos. 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 turn those insights into the digital experience maturity assessment.

11:12 In 2 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. 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 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 type back to it. I was like, I think this is wrong. This interface doesn't exist. What about this? And it comes back. It's like, yeah, you're right. Which I 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. So, anyone who's listened to this podcast knows I can talk about AI prototyping tools for the whole podcast, but I want to turn back the clock again to your next role after Internet Explorer when you're working on Outlook, another billion plus user product and I 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? 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.

12:51 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 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 was definitely a new thing when I think about that in like the 2000s when we were doing it. 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, okay, great. How are we going to do this? How strict 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 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. but yeah, I felt like those were a lot of the problems we were wrestling with as like these new features helping people communicate quickly. 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. I remember having lots of debates around that and where we should go. 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 Balmer at the time is like we need threading and then it slowly works its way down the execs and then it split up amongst tw 10 PMs or how did a feeder like that get built? 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 Balmer and Satia all of them were completely different. I felt like Bomber'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 kind of got delegated down. So when back when I was like an ICPM like my lead or my GPM or something like that, we'd be having those discussions around which features and be like hey somebody shipped something first. We'd be like okay let's go use the product play with it. in the case of threading it was more just like an idea we had internally and we're just like hey this will be really helpful.

16:28 Everyone hates dealing with this. So, we kind of go write one of those massive PRDs, you know what I mean? Spend a week and weeks like researching in a very kind of 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. 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 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 flipping the UI for like RTL scenarios. Where are we not? It's like accessibility thing through all the details of that. And I 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. 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?

18:07 Yeah, I think one of the biggest ways it changed was probably 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. 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.

18:34 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 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 on board. So I felt like we got a lot more tied to customers which was great. The span of control kind of got bigger.

19:15 Design got a stronger voice. which were all like positive trends. So a lot of the changes within Microsoft reflected the changes broadly within the industry. Yeah, I think so. I mean I think they kind of happened a little bit slower than I would say were definitely happening at like other companies. 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 Balmer 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 it missed on mobile, you know.

20:09 So those were like two huge trends to be like late to and I think Satia came back and was like very clear on like what the priorities were. We need to go build a cloud. We're going to go win here. Here's how we're going to 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 moved the company forward to like a modern SAS 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. and then trying to kind of do something more like Apple where it's like deeply integrated.

20:59 Wow. What are the lessons you learned from seeing SATA? Yeah, I mean I think that I I'm a pretty big Satia fan, not just because I was at Microsoft for a long time, but I think he's just a great leader. 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. 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 going to really rightsize 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? being first to regulatory environments and doing that. And I think that was great. You know, he allowed us to experiment more.

22:10 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 going to give away some of that for free like we're going to 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 want to go do it."

22:43 And I felt like Satia 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. A Quantive didn't work out. Some of the other ones, 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.

23:05 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 strengths having office and everything. I think GitHub was like the other big one the developer social network to some degree and like winning back that developer community. 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 and I think there's a good strategy around that like if I think about that like if you're an engineer today 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.

24:00 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 pretty much all AWS, you know, bigger enterprises probably usually lean more to, you know, Azure in a bunch of cases. 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 and it shows up in the stock price right I think when he came it's almost like nine or 10xed I feel like 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 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 your IC to manager or even you eventually I believe made it all the way to VP. Like how did you make those steps up the career ladder? 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. 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.

25:34 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 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?

26:06 Cuz like once you get a team in a charter, there's this just natural like, you know, momentum that happens of like you're just going to 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 where 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 cuz like if you're doing well the company wants to put great people on great problems, you know what I mean?

26:32 And like I guarantee you, you know why 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 u was there. my first time becoming a manager. I think a lot of that was probably building a network of people. I I'm not like the biggest networker. 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 want to go learn something new. I want to go learn how to do a vzero you know like and so I went to the one drive 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 want to store files in the cloud. I don't know what's crazy place for them to go upload them and like that became like one drive and I was there till the first like few million users. We bought this company folder share that I led afterward the sync engine and like sync story for and 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. 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 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 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 going to 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. and I think it it kind of limits your growth potential.

29:10 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 bringing bringing a fair amount of skills so you can like hit the ground running. I think moving through like you said to like VP and things like that. a lot of that is probably better understanding of the business context and how to work with go to market kind of 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 going to go use?

29:46 What is that onboarding experience? How is a AE going to be talking to a customer? Which customer should they be qualifying? Which ones should they be disqualifying? Right? Like how is an SE going to 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?

30:10 I think PMs overall want to make customers happy and that's definitely what like drives me fundamentally. but there's a negative side where they also just want to give away everything for free and it's like we do need the business to make money. So like thinking about okay great what is that line you know 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 look at as really end toend business ownership is really what I think helps you kind of get through that GPM thing into director senior director and VP is really like owning that today's episode is brought to you by Maven the problem with most courses online like Udemy is there's no live component and And the instructors aren't experts in their fields, they are 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/acos.

31:17 This includes courses like AI prototyping for PMs, product sense for PMs, and getting an AI PM certification. Visit it now at mavve.com/x a kh. And then I think another part of it is around communication. So understanding who the audience is and being able to pretty like a real-time adapt like you know when I would go into a meeting like the few that I had with like Satcha or I remember doing a big demo with Nat that we did for Bill Gates 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 because he wasn't as hands-on 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 I think you know the way I would talk to him would be different than how I would be talking to like Satia versus be very different how I talk to my engineering manager or the engineering lead or the marketing team and I think this 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 a 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 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 IC track or thinking about director, senior director, VP. 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 want to 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. This is one of those lessons I maybe didn't learn early enough. If I look back at some of my career, like I was a director of product at a firm and I feel like I should have done that probably. I was leading like 30 engineers at one point and like we there were times when I was like, "Yeah, we probably could have 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 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. 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 crossunctional 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 building great products, but that's not going to help the business succeed because you can have and there have been plenty of products that have been better and still lost. So, you really need to think across that whole thing of like the marketing, the messaging and expanding that breadth. I mean, I think 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 kind of going there where it was like close but not through that far. I think as much as I changed teams internally, I I had a bit of fear around just like it's so comfortable, you know, you get you get tied into these systems. And 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 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 want to 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 should be thinking about do you want to switch within your company or do you want to 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 learned because they're going through hyper growth. Like we're definitely feeling that at Vanta.

36:36 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. so like that's exciting too. But I think like challenging yourself on that fear and it was like a trap that I felt like I fell into and I felt like I would have learned more quickly if I would have done that. But I think the problem is if you stay somewhere less than 2 years, 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 cuz 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 and 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 kind of become like a mercenary, you know, 100%.

37:28 So, GitHub is so cool. That's where you went after Microsoft. And before you even talk about life at GitHub, what do PMs need to know about GitHub? Yeah, I mean, I think for me, like, 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.

37:59 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 co-pilot 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 highle 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 8 to 12 engineers like every week, you know what I mean?

39:21 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 want to 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 want to say like we want to go rearchitect this and it's like well why do you want to rearchitect there's a reason and it's like oh because like we see tons of bugs. I was like, "Okay, great. So, we want to improve quality and we like that's the big message like we want to improve quality for these customers. You know, we can look at this data. We can see SLAs's were 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 want to make build times faster." And I think a lot of people will be like, "Why are we doing this?" And it's like, "I want to 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 want to go do this thing? Because 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 kind of keep the lights on, keep the quality there and improve the quality that isn't just shipping new features. And customers expect because 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. We get in there and you're like, "This thing doesn't actually work." 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.

41:42 They just might not naturally talk about it that way first. That's the newsletter that comes out today. So 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 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. What is it like? You know, how are you we talked about like you need to make impact outside of product 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 you're kind of 24/7 on, right? 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. So that's how I experienced the role. How did you experience the role? 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. so hey there's an incident you need to get on and go deal with it and like the buck kind of stops with you from like the C team because sometime some companies and I think GitHub was more this way like Nat when he was CEO would have relationships with the IC's 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 want to 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 really I think a lot of it the winning the deal fell on the sees. So we spent a lot of time and we're really close to 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 for usage based billing which we had never had before. We had just been seatbased 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. 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 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.

44:42 And so I every day am like using the product and going through like basic cut 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. 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 want to make sure I'm connected to like what we're building because I feel like if you lose that, 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. and so I think staying close to the product but also understanding this like larger business accountability. 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.

45:25 like you know there are 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 because 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 because it kind of feels like can feel like BS work and like not valuable and like I don't know 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 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.

46:34 you know like I I don't know I probably have one especially advant but even I was 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 want to dig into something deep if you're 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 for those calls So, I think you start spending a lot more time on that as well. Okay. Sounds scary.

47:10 Sounds like a lot of work. Sounds like a lot of messages. Yeah. And a lot of meetings. Yeah. I mean, I think for me, I am continually trying to do a better job managing my calendar. 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 seven 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. 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's 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 going to make the job really exciting and I think make you impactful especially if you want to be in a more kind of like founder mode like style startup. 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 and making decisions. 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 going to write docs 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 so similar as you she says she still PMs like one feature a quarter you know it's like you so need to be close to the bare metal. 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 want to do this and she's like yeah of course like 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 like she's super talented. 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 in this flow and like how can we cut cut like some of the ways I think design can be the most impactful is as an editor and PNS as well which is about 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.

50:33 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. 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 want to go do for, you know, we do security and compliance software. We think about like vendor risk management is a big thing for us.

50:58 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 want to 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 going to help the business like drive revenue or usage or like whatever the outcome you're trying to drive is. So now we've alluded to your CPO at Vanta. A lot of people want to get a role like that. Vanta is one of the hottest companies. It's growing really fast. talk to us a little bit about how you got that role. Yeah.

52:02 it was an interesting process. I I think for me I had been at GitHub like three or so years. I was getting 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 to make it really successful. I think I was also like if I'm going to go that early I want it to be my thing so I'd probably just want to found again. but 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 one drive or consumer products or developer products and yeah just started meeting with founders I mean I think 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 firms that I'd known and worked with in the past, they were telling me about different jobs that were there.

53:25 different recruiting firms were kind of like reaching out and I 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 conversations started to happen. and yeah, I met with Christina like I don't know, maybe I've been looking for like six months or so. It could have 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." but at the same time, I wasn't sure if I really wanted to leave like GitHub yet, but I felt like I did.

53:55 And a rework happened there. My team got even bigger and then I was like, you know what, I I don't want to leave. Like we had two good conversations and I was like, I'm happy here. This is all great. 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 interesting. 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.

54:18 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. and Christina had reached out again then. I was like yes like let's like let's talk more. And yeah, it was 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 because we had like a GitHub conference in there with her doing it. 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 kind of 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 do you think our working relationship would be great?

55:08 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. and yeah, I felt like it was great with her. And got to meet some IC's for the team, which I thought was really great.

55:27 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 IC's on the team. So, I actually did a couple calls with IC's. I got to review a bunch of their specs. I got to go meet people from go to market and I 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.

56:07 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 want to 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. I was like I don't know just like go talk to like Josh about this like you know what I mean? And like so I like that type of culture and I felt like we were really building that there.

56:32 Really loved like the leaders and like revenue and everything. And I think I've seen and talked 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 Bant 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.

57:03 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 because like I don't know like just on my team, I think we hired like 40 people in the last quarter and 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's some chaos, you know what I mean, with that. 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. 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. So most people have probably heard, you know, I think Vanta has been advertising on Lenny's for years now.

57:46 They've heard like the basic pitch, right? We do sock two 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 the secret sauce behind Vanta success? Yeah, I mean I think we have a couple different products and I think there's the one that probably a lot of people see through line 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 SOCK 2? Do you have ISO? Do you have some certification to let us know like you're going to take care of our data?

58:29 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. They probably don't have experience in it or like CTO's 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. And so our goal is like, let us come help you.

59:20 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 talked 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 want to go sell your product you're going to 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 could just ask questions to get answers and not bother the security team 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 grow the breadth of our offering 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 going to 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 are 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 and 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 and like you know helping you kind of go through each of those pieces. Okay. So you guys have really become like a full cyber security platform for CISOs and it's not just that 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? Yeah, I would say from obviously the like upmarket customers drive like much bigger deals as you would imagine, but I would still say fundamentally our business is primarily a down market business and we never want to 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? or 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. 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, well, 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 stock, too, like you you have no idea what to go do, 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 because we can talk about our value, what this process looks like, how we're helping you with everything. we're going to connect you with a pin tester and we're going to 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 and then trying to continue to add kind of new products to kind of 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 kind of 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. so you guys, I think you probably are proud of when most innovative security company last year. So a lot of that has to go to the product people. you and Christina probably at the top of that. What are the unique things about how you guys build product? Yeah, I mean I think that in my opinion I've tried not to throw too much shade here. I would say like most security products have a pretty terrible customer experience and 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. 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. you know, we had a design team, but I brought in Deb. She's like an amazing design leader. and we've really invested in building up and giving design a much stronger 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. I run, you know, I think a lot of other companies are called product reviews. I call them like deep dives because I don't want it to feel like like a review, like you're getting a grade, but every week I'm in at least one of those where like I am seeing demos from the team where we're walking through Figma files, you know, I 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 want to 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 road map 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 hm 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 kind of 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 endto-end scenarios and the problems and are those really coming together and then really like unleashing engineering just to like 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 focus 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 want to ship a feature like you know commenting or notifications or any of these types of things or enhance it it just kind of gets better everywhere or it's very little work to kind of 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 want to 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 windsurf or some of these like new editors with built-in AI capabilities to move like even faster?

67:14 awesome. So, if we think about it, you are trying to really embrace all of these AI software out there. 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 three to four months? I think Windinsurf is four months old you guys are adopting it.

67:49 Yeah. Yeah. I mean, I think we encourage people to really try things out, we put a couple guard rails. I would say the biggest guard rail 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 Bant. 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, like OpenAI or whatever else. but I think that's like the hard line, but other than that, we're trying to like really experiment.

68:26 and so we have multiple different teams where people are kind of like running off 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 macroware like what's happening in industry overall micro, what are we delivering, what are we triing, what are we doing. We try to build a strong culture like even when we did the vzero thing is something I was really excited about because I know the versell 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 know 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 going to do enablement for this. So, like I actually just recorded a Loom file and 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 vzero 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."

69:26 And recorded like a 20-minute like Loom demo. And then like now like every PM is producing things. you know, for design we use Figma. So, we got Figma AI and are trying to push that trying to connect that with code connect into cursor and different pieces. So, I think the big thing is to not be hands-on. you know, you kind of need to set some reasonable security guard rails for us, which is like don't never put customer data in these things. but outside of that, I think you should really be open.

69:53 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." 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 onetoone 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.

70:35 Like you know 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. and we have such close relationships with like Figma and Verscell and many of these other companies, it's like, you know, very easy for us just to like work with them and collaborate and give feedback. So, we talked a lot about PMs getting oriented towards business outcomes. We illustrated how that happened over the course of your career.

71:12 How do you evaluate PMs at Vanta? Yeah, I I think there's a couple key things for me. 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 what he always referred to as like the three Bs of program management or he was like big brain he kind of called it like how good are you at like vision and strategy and doing that bulldozer how good are you just like just getting stuff done even if there's a wall you were just going to like plow through it and then like bridgeuer 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, four, five, six, 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 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 want to go into management, it's also a lot of like how are you getting the most from your team, but still making sure the people don't kind of 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 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 a million% 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? 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. so that in and of itself is a great template, but I want to ask if a new PM joined your team with no experience.

73:56 What is the advice you would give them? Yeah, no experience in kind of like program management or product management. Maybe they were an engineer like you started out at. 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 is 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 risk for the company and like securing the actual like foundations of the software that they're building in the company, but instead they're answering for the 3 millionth time like do you train on my data? What is your encryption level?

75:13 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 going to save these people on your team like 5 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 so I won't say their name but they were like literally after Vanta they're like he's like I could work 3 day weeks like it has saved so much time for me and this is someone that's the higher end were 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 want to 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 road map 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. it's a little bit different if you're in kind of an ads driven business where like you're not like selling SAS and all about usage and utilization and things like that. But if you are in SAS 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. I would say also like get on sales calls. Like be on there.

76:57 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 I was like we were talking to companies that were like 10 people or less like or five of them and like you know you know 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. 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.

77:53 Couldn't agree more. Jeremy, thank you for doing the pod. Yeah, thanks for having me. This has been a great conversation. Hope everyone enjoys it. If people want to find you online, where can they find you? Yeah. I'd say you can find me on LinkedIn and on X as well. Just Jeremy Epling on both of them. Keep it simple. and yeah, I think one of the big things I just leave everybody with is if anything here excited you, I would love to chat with you. we are hiring a lot in product engineering, design, but not just there.

78:21 We're hiring in go to market and 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 joining just doing tremendously well. So yeah, there are these career launching companies for me it was Thread Up. It was like I joined it at series C, made it through series E, now it's IPOed. I think those are the type of companies you're looking for at a certain stage of your career and I think Vant is a great example of one. Yeah, definitely. 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.

79:09 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.