Executive Function: Building systems that can make decisions without you | Jeanne DeWitt Grosser (COO, Vercel)

Jeanne: I think a lot of executives over pattern match and do not have intellectual curiosity to figure out what's different.

Brett: If someone's effective at 25 million in ARR and their goal is not to be layered or managed out, are there things they should be doing?

Jeanne: You need to work yourself out of a job. You're comfortable doing the job you have become good at. That is no longer the job.

Brett: What do you think are the things that tend to keep star talent from ascending to sort of the top spot, in maybe any functional area or in the C-suite?

Jeanne: They try to scale via what has made them successful so far and basically just continuously become a super IC and so you now have to design a system. You have to understand what are the metrics that you need to be watching? What are forums that you need to review? Who are your key people?

Brett: Is there a performance review that was the most valuable?

Jeanne: One of the things he said to me was cross-functionally, when you don't think somebody's good at their job, they're dead to you. You can't unhear that.

Brett: Well, let's do it. Thanks so much for joining.

Jeanne: Thanks for having me.

Brett: I wanted to start by getting your perspective. When you think about being an executive at a scale-up startup, what's the difference between somebody who's very good and someone who's extraordinary?

Jeanne: Some of what I would say is, and this is something that Stripe valued, and I think a lot more companies are generally valuing this, which is you have to be able to operate simultaneously at 30,000 feet and ground level. So from a 30,000-foot perspective, you have to develop a multi-year point of view on where you ought to go and how to get there, which I will say feels harder than ever in the current moment that we're in.

Brett: Just given the amount of change.

Jeanne: Yeah, with AI. You just don't really have a sense for if I put together a two-year plan, is that reasonable? So I think that's one. And then at the same time, you are still hardcore building a company. So there are all sorts of operations that are not yet operational, and there can be a pretty big gap between that 30,000-foot view and what needs to be true to realize it. Not everybody at your company has had the experience before to know how to go and say, "Okay, well, this was Jeanne's North Star. I know how to turn that into an hour by hour, minute by minute operating reality." And so, you're in some cases building that yourself. You're, in other cases, coaching somebody who has the will, but not yet the skill, and then in other cases, being able to delegate more freely to somebody who has done it before and can bring that vision to life.

Brett: How do you think about those two big jobs to be done in various points of scaling? So if you're at a 500-person company, 1,000, 5,000, 10,000, does that change pretty dramatically or do you think it's somewhat similar?

Jeanne: I think there are parts of it that are similar. So when I was at Stripe, we were, I think, 8,000 people by the time I left. Vercel is now north of 600, and as a leader, I'm always sort of figuring out what are the three big rocks that either I'm not going to be in the weeds on, but I'm going to be reviewing and very, very close to, or the things that are so hard to figure out exactly what's the right way to approach it that I'm going to get in there almost like an IC alongside the working group. I think as a company scales, if you've done a good job of hiring, you do have more people that you can give a North Star to, give a set of metrics to, and you don't have to be in the nuts and bolts of that thing, so it's a bit more maybe of an altitude question, but it doesn't change the fact that as an effective executive, there are a set of things where you're going super deep, either personally doing the work or deeply, deeply reviewing it, and then a set of other things where you have confidence that the team's going to go execute without you being super close.

Brett: And maybe if you take a snapshot across a couple of the points in your career in the different executive seats, what is the outcome that you are responsible for? As an IC, it's very clear you're a PM, you're working on a product, or you're an engineer, you're deploying some piece of code, but do you think about it? I mean, you spent a decent chunk working on different parts of the revenue org that it's just, "I have to hit this number in this segment and that's my job," or you think about results differently than that?

Jeanne: You're thinking about things on multiple time horizons. So I am accountable to specific results within a year, but an executive is meant to be long tenured. My career has been marked by basically two nearly decade long tenures. Hopefully, Vercel will be a third for that. And so, executives have decade long stints because you are able to replicably produce results year after year after year. And so, that means the bulk of your team is going to be focused on executing for in year results, whether that's in product or go-to-market, et cetera. You have to have a set of leaders who then are also capable of thinking about, "Well, what about next year?" And then, you, as a leader, need to be thinking even past that. How is the competitive dynamic changing? How is the market around me changing? I work in sales, but how do I feel about our product roadmap relative to what I'm seeing in customer conversations? I think that's probably the other thing that you're doing as an executive is you've got a functional swim lane you own, but most effective executives are going to be looking more broadly. Do I feel like the finance org is using the right set of metrics to measure success and allocate resources? Again, do I feel like product has the correct roadmap that's constantly going to keep us competitive? And so, I think any really strong executive typically is thinking more as a general manager with depth in the particular thing that they own, but also an ability to make trade-offs that might not be in their own self-interest because it's going to set them up for success or the company up for success really in the long run.

Brett: Are there things that tend to keep star talent from ascending to the top spot in maybe any functional area or in the C-suite, CRO, et cetera? So they get up to being a star VP of sales, and they just never become one of the generational CROs, or they are in any of the other functions. They're an incredible VP of ops. They're never going to be a COO if they're coming up in that. Are there things that tend to stitch together all the people that get stuck other than bad luck or they chose the wrong company or anything like that?

Jeanne: I do think it's an ability to transition into systems thinking. So if you move from an IC into an operator into a leader, it's not about you anymore. It's about, can you get a group of people to execute the way you, as an IC, would have done a thing? I think actually, one of the biggest leaps in leadership to make is going from a frontline manager to a second-line manager. So there, you've got to learn to delegate and get comfortable with that, but you're going to seven direct reports on average. You're pretty darn hands-on. When you get to manager of managers, you can't now go and be in every deal, be in every product review, all that type of stuff. And so, you now have to design a system. You have to understand what are the metrics that you need to be watching. What are your leading indicators to know when something's off track? What are forums that you need to review? Who are your key people? How do you keep a pulse on what's actually going on through them? And so, I think often, where people get stuck is they try to scale via what has made them successful so far and basically just continuously become a super IC rather than empowering the other people around them to be excellent ICs as well.

Brett: What's the balance there between sort of empowering people and also being in the details? I think one of the things that you started to say, and I think my guess is knowing you a little bit over the years and certainly the culture of Stripe, is that there's the altitude shifting. And so, it's not just, "Here's my six leads underneath me. I'm just focused on them," there's a lot of diving into the details. And so, how do you think about that in what conditions you're sort of behaving in what way?

Jeanne: I think a big thing for a leader is pattern recognition. And so, one of the ways I get at that is by staying close to the most effective people at various layers in the organization. So in a sales org, as an example, I will spend a lot of time selling alongside some of our top sellers because I want to see, is their messaging evolved? Is my pitch starting to diverge from their pitch, and what does that mean about my own/the one that a hundred other people are doing? Are they getting a new set of objections that they're handling effectively? So that's sort of one way I'll do things. And then, the other one, I mean, it's sort of different version of an earlier answer, which is the projects that are key to driving step function change in some area typically at the outset. I'm in the room with you doing the whiteboard. When you write your first brief on it, you've got a comment on every other sentence from me on how to do something. For the first three meetings while we're getting the project out of the ground, I'm there actively participating right alongside you. And then, when I sort of feel confident like, "Okay, this thing's got exit velocity. Great," we'll go into biweekly, monthly, whatever's an appropriate review cadence because I now sort of feel confident that we have a shared mental model, which I think is another big thing you're trying to do as an executive is... One of the things I always feel I've succeeded is I'll have people work for me say, "Jeanne, I was in a meeting earlier today. We were discussing X, Y, Z, and I sat there and I thought to myself, 'What would Jeanne do?'" And if I've done a good job of helping you understand my mental model, then nine times out of 10, you should be able to ask yourself that question and come up with the answer I would've come up with had I been there alongside you.

Brett: What are examples of the types of things you're trying to teach?

Jeanne: I mean, so you can have processes that facilitate this. OKRs are an example of that, all hands, how you communicate priorities, staff meetings. We always kick off every one of my staff meetings with Jeanne's top of mind, which is meant to communicate my mental model. So maybe some other things within go-to-market, actually at the company, this has been helpful is a segmentation framework, so we can all talk about customers the same way. We talk a lot in go-to-market. I'm a big proponent of lead to revenue models. I've run operating model where you've broken down all the funnel math, so we can have a similar way of evaluating performance where things are green or not. Those are other examples. I think of like operating mechanisms that basically also give you a shared language. Another example of that actually within sales is often, you'll have like a sales methodology that you brought in, which lets you... I mean, MEDDPICC is a common discovery framework, but it's also another way to speak the same language. I think that's a challenge you can sometimes have at companies where you're sort of speaking past each other. And so, shared metrics with common definitions, that's a great way to have finance, product, sales, all speak the same language. Segmentation framework often at companies is a go-to-market thing. At Stripe, I strived really hard to have that be a company thing. At Vercel, it was a little easier to just come in, and this is going to be a company thing. And now, actually, every new hire, I deliver one of our company values is KYC, know your customer, and I deliver the KYC onboarding session where I walk through every new hire at the company, "Here's how we think about customers, how we break it down. Here's what our customer base looks like." So again, you sort of have a shared mental model across the whole company.

Brett: What do you think are the hardest areas of the business to develop shared context on a team?

Jeanne: A lot of startups is product-market fit, right? So when you aren't yet replicably selling into a segment, a vertical, however you're cutting your customers, is that because the product isn't good enough there or is it because your go-to-market isn't strong enough there? So we're going through that one now at Vercel where really beloved product by startups and developers, we've had some awesome enterprise wins, but to what degree do we actually have enterprise product-market fit? You get situations where you've got these wins. So if you work in product and engineering, that suggests in your mind, "Well, if one enterprise brought it, surely all of them can, right?" And so, this must be a go-to-market problem of like, "You're not doing a good enough job of bringing forth the value of our product and all these other enterprises," whereas a go-to-market team might say, "Well, actually, we have the following feature gaps that we need to do to make this more expansive." So we're trying to, right now, get at it both from a data-driven perspective of just objectively speaking if you use that three by two I just articulated. Where is our revenue today? Where is it growing organically? And then, within go-to-market, preparing our point of view in each of those boxes for each of our product lines, what's our view on the degree to which we're totally green? We can sell this to every company on the planet in that segment versus, "Hey, we're halfway there. There's a set that we're really strong at and then a set where you might need one or two things, and then here's where we need to build into," with the hope then that we can agree on those and either we put in certain things on the roadmap, and therefore, we'll plan to go pursue revenue in that segment or we say, "This is not the year of X product and Y segment."

Brett: If you take a step back and you look at your job of being the COO of a 600-person company, and you would take a blank sheet of paper out and sort of just start from scratch to say, "Okay, what is the job description of a COO by your definition for a company at this scale," what's on the piece of paper?

Jeanne: This is one of the tougher things about the COO role is there's not sort of a canonical definition of a COO to start. my functional job at Vercel is a soup to nuts go-to-market role, so I have marketing, all of sales, all of your technical sales functions, customer success, support partnerships. Basically, if it touches a customer, makes a dollar, it's in my remit. That's not necessarily the typical COO role. If you took Stripe under Claire, she had people but didn't have marketing at the outset, had marketing at a later point. I often think COO is sort of like the set of functions that a founder knows are incredibly important and doesn't personally want to manage at this particular moment in time. But broadly, I sort of think of my job as two things. One is go execute the functions that I run excellently, turn those into predictable engines, and then two, enable the company to run more effectively. And so, that'll be things like company planning, or even though data science doesn't roll up into me, how do we have more uniform metrics across the company? How do we do things like a segmentation framework? There's places on people that we want to dive into. Our executive team is doing a half-day offsite tomorrow, and one of the sessions I'm leading is we're currently doing planning. And so, that's a lot of the what of what's going to be the revenue target and what are we going to do to get there. Tomorrow's session is all about the how. So when you're scaling as rapidly as Vercel is, there are going to be a lot of things that are working about your culture that you actually need to be thoughtful about ensuring you carry forward and then certain things that worked really well at a certain scale that aren't going to work at the next scale that you might want to refine. So we're going to spend some time talking through our-

Brett: How do you figure that out? Is it just judgment?

Jeanne: I think like a lot of well-run companies, we use Culture Amp. So we actually do our employee engagement surveys. We just shifted now to doing them three times a year. So you have data about the places that your own executive team thinks things are and aren't working. Your employee base does, so bring that to bear. And then, I'm planning to basically also do a bit of a stop, start, continue of just like four folks in the room. What's our views on the things that are working and not? And I think that'll be elucidating on the degree to which we all agree. I imagine there are going to be some places where we do and others that we don't, and that in and itself is something that you want to surface and work through because if executives don't believe on an aspect of the how, you actually will not have cultural uniformity on a thing that might have, say, been really important to Guillermo and we did in fact need to codify.

Brett: And you're doing this with your exec team or the exec team by the company?

Jeanne: The exec team, so this would be chief product officer, CFO, head of people, et cetera.

Brett: What's the benefit based on your time at Vercel of packaging the COO role in the way that it is at Vercel as you outlined? What are the trade-offs? Clearly, there are downsides to any given org configuration. How would you kind of group those things?

Jeanne: One of the things I'm really excited about in it is it does give end-to-end ownership of the customer experience. So we are the external facing functions. You do have a singular owner of the revenue, right? So you can't have sales point its finger at marketing. Marketing points its finger at sales because I own both of them. So it's my job to make that work. How I often describe it is I feel like marketing and sales end up being this like Venn diagram of strategy, and then you have the same thing actually with sales and support often, and then everyone winds up doing each other's job. And so, I think if I'm doing my job right, that feels more like an integrated strategy and a continuum rather than somewhat overlapping set of goals. I think that's the benefit. Similarly, from a feedback into the product and engineering org, you often have support has this set of asks, sales has this set of asks, marketing might be thinking about what we want to sell in the future, they have this set, and now, EPD has to go decide of these three inputs like how do I stack rank them? Whereas if I'm doing my job effectively, I ought to say, "I've looked across all of these and here's what I think is the right strategic mix of those," I think those ought to be the benefits. From drawbacks... I mean, a COO role has a fair amount of breadth. So across my functional remit, I have places where I have depth and places where I've historically been adjacent to that. And so, I have a lot of exposure to it, but it's not like I'm a 20-year marketer. You've got to believe I'm going to hire well and then manage well for that particular function. I think that's often true with a COO is you'll spike in certain areas, and then you sort of have to believe you can cover the others.

Brett: Why did it make sense in the context of Vercel, specifically in the marketing function, the roll up under you, given that it's such a marketing and brand-centric company? The natural thing I think is you see a founder that has those type of brand and taste sensibilities, and so they would want marketing very close to them and not being disintermediated. Was it just that the entire owning the end-to-end customer experience is so much more valuable that the trade-off is worth it basically?

Jeanne: I think so. I think it's interesting. I mean, marketing is brand and then it is the tip of the sphere-

Brett: Demand gen and everything else. Yeah, exactly.

Jeanne: Demand gen like tip of the sphere of your revenue engine.

Brett: Exactly.

Jeanne: A lot of founders, Guillermo's a good example, John and Patrick were examples of this as well, are excellent brand marketers, but that does not a predictable revenue engine make on its own. And so, I think that G and I got to a point through the interview process where he had enough confidence that I was going to let him continue to be chief brand officer, and then I could go build that machine that was going to drive our B2B growth.

Brett: So do you have that explicitly carved out or no, it's just more informal?

Jeanne: No, it's more informal. The way I operate as a leader is like... I've always been somebody where it's like, "All right, if you want to talk to a direct report of mine, you don't have to go through me, just go talk to them." It's my job to have broad awareness of what needs to be true to achieve the set of results we're going for, but I don't need to be in charge of all of it. So my CMO as an example, I'm like, "You should have weekly one-on-ones with G. I want you to know what he's thinking about. I want you to know all of the things he's concerned about from a brand perspective." And then, he and I can debrief and figure out when there are places where we might need to prioritize something differently or whatever the case may be, but I don't have a need to block any of that or be an intermediary of it.

Brett: How do you think about your role in the team that is under you in being incredibly demanding and supporting?

Jeanne: I think this is one of the things that people say is like differentiating about me is the ability to sort of be in that upper right quadrant of supporting and demanding. I think on the demanding front, one, it's a standard I hold myself to. Two, I think most people that I'll hire and work with really do want to produce excellent results. The thing then that is differentiating is the ability to bring the supportive, which is I'm going to bend over backwards to help you get there. And so, I think the folks who have worked for me for a long time, you get into that dynamic where you know, I'm going to be your best sounding board. I'm somebody who you can bring problems to that you don't have to be worried about. It's fine to take things to me in draft form, and we'll work through stuff. And as long as you're being communicative, upholding commitments, we'll figure it out. But when folks are not upholding commitments, not escalating issues, letting bad outcomes happen that we haven't tried to intervene and solve is sort of when you get into more issues.

Brett: Do you find that it's hard to calibrate or manage between those or it's just very intuitive?

Jeanne: Honestly, I think it's intuitive. I'm doing a lot of executive hiring right now. So we hired a CMO in June, just hired a global head of field engineering less than a month ago, in the market for a CRO. I spend a fair amount of time with those folks while in the interview process. One of the things I actually do throughout the interview process is a fair amount of coaching them because if I'm going to hire you, we'll have that type of dynamic. So in an interview process, I'm also here to set you up for success and see if we go back and forth in that capacity, does it result in you doing well in some of these forums versus sort of let's hang you out to dry and see what you can independently produce. So by the time I hire people, I feel like we've built a pretty solid working relationship. I meet very frequently with new executives when they start. You're trying to be in constant communication. So again, we can develop that shared mental model. I'm fortunate enough that our CMO and I take the same ferry to work, so he and I have all sorts of ad hoc one-on-ones, but you're pretty quickly just trying to get to that safe space of like, we are going to talk about the business, we're going to talk about how to make the business better, and then we're going to partner in the places where that makes each of us more effective and go off and conquer where each of us knows exactly what we want to do and can just go execute.

Brett: What's the core of an interview for you when you're running an exec search for your own team?

Jeanne: So my first interview is sort of like just bidirectional, learning more about your background, going pretty deep into the things you've done, and then selling you a fair amount in a very, not selling actually, mostly telling you, "This is the reason I'm hiring your role. I have the following issues that you will need to come and resolve." I find that by putting those things out on the table in the first meeting, basically, you get a sense pretty rapidly for, does that person get motivated by solving those things or not?

Brett: So what did that sound like for the CMO search when you're communicating, "This is the job to be done"?

Jeanne: Yeah. For the CMO search, it was, we're moving up market into enterprise. So we've got some early enterprise wins, but we don't have enterprise awareness, enterprise brand recognition, so we got to go build an enterprise machine. Second was we do not have an investible model, so I need somebody who's going to come in and build a real demand gen machine where we know we can put a dollar in, we'll get this money out. So I need somebody who is into the quantitative aspects of this. Another big one was Vercel now actually has a lot of product surface area. So had been known for front-end cloud, we now do a bunch in security. At the time, AI was still a little bit more nascent. Now, it's not, but basically, it was like, we're going to have to do some major positioning work to actually figure out how do you graduate into being a much broader set of products while not losing the core of what got us here. And then, you sort of describe the realities of some of the messiness behind all of that. So that's sort of like my first call. My second call, I typically send a prompt for before where basically, it'd be like, "Okay, I teed up these areas in the first call. Now, I actually want to go and spend this entire hour talking about those four and things you have done that are similar at prior companies and then how you might think about starting to tackle it here."

Brett: And what's excellence? You leave that second meeting going through that prompt and you're like, "I desperately want to spend more time with this."

Jeanne: Typically, I have learned something. I have learned multiple things.

Brett: Novel insight.

Jeanne: Yes. Often, early, that second meeting, they already are giving me a mental model I didn't have. They're talking to me either about a thing they did where I can immediately see, "Oh, if we did that here, it would work." So I generally lead that second call if it's somebody who has a shot at being hired, very excited about, "Oh, okay. I would be able to not pay attention to these things because you are better at that than I." Same thing just happened with the field engineering leader on that second call. He was pulling up some dashboards that he had built and talking me through how they run their proof of concepts, and I was like, "We do none of that, and you just pointed out five metrics that I've never heard of." So that's sort of that second call. Then, we fan out into meeting other folks. A lot of these rules at Vercel, it's incredibly important that you get product depth, and you will be credible with our EPD organization. So we've got those meetings. We're getting into people topics, et cetera. Then, we'll regroup coming out of those. Next one then is a 90-minute workshop. So there you are doing work product. We have three prompts. Typically, they align to stuff you would be expected to do in your first 90 days. And then, they'll do a one-on-one with G. Any executive reporting to me has got to be somebody he also trusts and would go directly to. Then, we'll do stuff with the folks that are going to be their direct reports.

Brett: What's the prompt in that second category?

Jeanne: Yeah. So CRO, we're doing right now. First one is effectively, we give them, "You're going to go talk to Nike's CTO." So Nike, the reason I picked this, Nike's on Next.js. They're not on Vercel. They have Akamais their CDN and WAF. They clearly are investing in AI, so they sort of have all the things you could possibly sell to them. And this person is going to have to figure out we are not yet excellent at executive selling, so I'm curious how they'll come up with a value proposition for that executive. I'm going to be interested in the degree to which they go really research our product and can speak intelligently to why if you're self-hosting Next.js, that might not be a great call for you. So that's sort of the first one is basically like, "Do they start to geek out on our product?"

Brett: And do you only give a one-line prompt or you're giving supporting material?

Jeanne: It's like too small. It's probably six sentences total, but it's two small paragraphs. So that's the first one.

Brett: If they ask you for additional information, do you give it to them?

Jeanne: So actually, with both CRO candidates that we're about to bring on site, I did prep meetings with both of them, which is also a really interesting interview. What do they ask me? How are they thinking about breaking down these problems?

Brett: In doing so many of these problems, I found that if you could not have somebody do the problem, but you just have the pre-call where they're asking questions, that's as high signal as the project itself.

Jeanne: I totally agree. I actually think that was one of the reasons I wound up getting employed at Vercel is I had to do the homework assignment, and they set me up with one of the VPs to walk me through. I can ask whatever questions, and I think I did. That was probably my best interview. But yeah, so our second one is all about, are you going to be a tight operator? So it's digging into what's your operating cadence, what are the metrics you're looking at, how would you drive results? So just basically looking at what's their machine and then in the conversation, can they contextualize it? So will they be able to say, "Hey, I did this really well at the company I'm at currently. Here's ways in which I think that would likely pull through directly to Vercel and ways at which I might tweak." Our last one is, I think Vercel is like a 99th percentile AI company, and one of the things I'm passionate about is bringing AI to bear on everything that we're doing and go-to-market to really build a unique AI forward experience. And so, the last prompt is about that. The world's your oyster. You've got a GTM engineering function. You've got a killer data science team. You basically blank check for me to go, "AI eyes what you're going to run. Tell me what you'd do." And there, I'm trying to figure out, are they creative? Do they have good ideas, or are we mostly going to be running out last year's playbook?

Brett: Is there a thread that ties together all the failed executives that you've hired in your career or they all didn't work out for all sorts of random reasons?

Jeanne: Maybe a more interesting way, just because at Stripe, we hired so many, so if I go beyond just the ones I hired, I think it was a couple things. One was typically, they did not actually go get their hands dirty. Actually, the thing I should have started with was they had a playbook and they did not contextualize it. So I think a lot of executives over pattern match and do not have intellectual curiosity to figure out what's different. We had a lot of this at Stripe where you had AWS consumption-based business model that feels like it ought to be similar, and actually, payments has fundamentally different margin profile. It's totally different competitive space, et cetera. So I think that's first is over pattern matching and not going and getting your hands dirty to adjust. Second was did not culturally adapt. I saw this happen at Google. I saw this happen at Stripe, which was like you ended up with... We had an Oracle leader at one point in the org I was in. And so, that org started to feel like a Google-y version of Oracle. So we had pockets of that at Stripe as well. And then, typically, it was also a failure to develop your network and collaborate effectively to get buy-in from other orgs.

Brett: Do you think in the way that you outlined how you approach evaluating exec talent, it's quite good at screening all that out, or these are the pockets of error that no matter what you do, it's surprisingly hard to figure that out before somebody joins and is eight weeks in or 90 days in or whatever?

Jeanne: I've gotten better at the, can this person contextualize in particular? I think a lot of times when you're hiring an executive, you get like shiny resume syndrome. And so, now, if you go back to the three questions I just outlined, the middle one is really meant to be like all my questions during that portion of the onsite will be like, "Well, how would you tweak it given this? How would you figure out whether or not that's relevant?" I'm actually looking for folks to open by saying, "Hey, I don't know enough about your context. I'd hypothesize the following might be true, and therefore, this is transferable." So if they open that way, great signs. If not, through the discussion, can we pull out mental flexibility? I think that's one. I think it's probably harder to get. I mean, the network one I try to get at by lots of cross-functional interviewing. So like Tom O, our CPO, is on all of my executive loops because he's got to be as excited about this person as I am. So that's meant to correct for that one. I mean, the workshop is a great way to force an executive to go get their hands dirty. A lot of those people won't have written a two to three-page doc by themselves all alone for a long time. So you'll have to bring me back a year from now and see if I've done a good job with everybody.

Brett: Do you think most of the best executives were extraordinary I see in the function or it's non-correlated? So the best CRO at one point was an unbelievable seller, top 1%?

Jeanne: I tend to think there's some of that. I do think I'm better at my job having been deep in sales within the COO remit. I am better at how do I really push the sales org than how do I really push the marketing org? Because I know in sales, when I am making an ask, that is hard, but it is reasonable. Whereas in marketing, I may not have that same reasonableness. I do think that that matters. Also, somebody asked me a question along these lines at a dinner a month or so ago, I hypothesize it may matter more in the AI era because a lot of what you're trying to do is now in part functional acumen, not only to your team, but to an agent. A very tactical example of this was I launched a GTM engineering team in the first six weeks on the job at Vercel. So basically, it took three sales engineers like, "Congrats. You're now founding members of our GTM eng team where we're going to go bring agents to bear across everything in GTM." The first thing we tackled was building a lead agent, so people who contact sales. This would help qualify them more effectively. So we had one of the GTM engineers work with a top performing SDR on that team, and they did a lot with human in the loop. And basically, after about six weeks, we were ready to largely take humans out of the loop because it was now performing in line with all the human-based KPIs we were using. Then, a couple of weeks ago, so this has been running since the start of August, we now have built this thing called a playbook platform where we have all these plays that have agents running. So I was playing around in that to go make sure I'm still aware of what's going on in this playbook platform. So I click in to some of the emails that the agent is recommending we send as a first response, and I was like, "Ooh, that's actually not what I would've said." I realized it's because even though that was modeled after our best in class SDR, I have 20 more years of sales experience than that best in class SDR. And so, I know a little bit better what you should say if an executive wants to talk to you about a product than that person did. I think you're going to see that across a lot of places where actually, functional depth combined with your depth of context in your company, those two things together are kind of what makes AI work better.

Brett: What have you figured out about metrics? What is kind of persnickety or difficult about them? What are the things that seem obvious, but when you run a business on this type of number, there are these issues. Do you have wholesale like you spent so much time trying to govern businesses as they scale with numbers? Is there a handful of things that you've figured out that are kind of truths in what goes on when you pick a number?

Jeanne: Two things, I would say. Thing one is I'm a huge believer in driver trees. So literally, can you start at the top total revenue and break that down into the hundred different nodes that actually drive that outcome? Can you do that X anti so that throughout the course of the year, if revenue is green or some other color, you know exactly either what's working well that you can lean into more or what's not or you can course correct? That is like a biggie that I try to get in place anywhere.

Brett: Which you would think of as like leading metrics or drivers to some lagging metric or output?

Jeanne: Yeah. It's basically, okay, you've got total revenue. So what is that going to be? It's going to be net new revenue from new customers. It's existing revenue for existing, expansion from existing. Okay. Net new revenue, that comes from, you can break it down by segment all the way down to the bottom. So that was actually one of the first things I did my first 30 days at Vercel was in the go-to-market side, put together a lead to revenue model, which is here's exactly everything that needs to be true, how many leads we're going to need, at what rate will those convert into an opportunity? At what rate will we win them? What will be the ACV? How much time will it take by segment, by geo, massive model? And you want to do that at a company level as well so that you can be aligned across the engineering side of it, too. So that's sort of one is actually understand your drivers and which are levers. So I'll give you another example on this. When we did the lead to revenue model, the model for Vercel this year was most sensitive to our ACV. So the most credible way for me to increase revenue growth rate was that particular area. Similarly, in our PLG funnel, we also built the lead to revenue model where that one, the biggest one was actually our signup conversion rate. So that helps you figure out where to focus. So two is actually the definition of a metric. This was a challenge we had for a while at Stripe when we brought in a bunch of new executives at the same time. Sales will define revenue a certain way, typically more bookings oriented. Finance will define it differently, perhaps gap revenue, and EPD might define it another way that might actually be more usage oriented than actually the revenue dollars, or it might be revenue dollars, but some ARR variant. I've frequently found that if you don't have the exact same definition, then you can have things be green or red depending on how you're cutting the data and looking at it. And so, that was a big thing that we focused on for a while, and getting right at Stripe was a singular way to review the business across go-to-market, EPD, and finance. Go-to-market could then lead the room and run a forecast call with the way we were going to look at quota and target, but you needed to report out on it collectively with the same way to cut the data. We sort of had the same thing actually coming to Vercel. I sat down with finance to look at that one as well because we had a quarter where you had one result on bookings, but actually, sales was super green, but you'd had a churn somewhere in the business. So total revenue that the company was looking at was different. So I think that's the biggest way is we cannot debate metrics. They have to be set, definitions agreed, and then we're all out, and we all agree. If this is green, we all think it's green, and if it's not, we're all fixing it.

Brett: What was the difference between how the group decided revenue should be accounted for at Stripe and the way the group decided revenue should be accounted at Vercel, and how does that map to how you actually go about bringing clarity to a given metric?

Jeanne: Stripe always had, I think it's shifted more since I've left, but payments was one of the earlier consumption-based businesses, but it was really unusual for a long time to do a committed contract because payments actually is arguably maybe the first ever consumption-based business. And so, sales would sign deals, they weren't technically bookable, so you were sort of approximating the value of them, and that may or may not realize. That was one of the things that sort of would get us wrapped around the axle sometimes. And then, sales looks at stuff again on the basis of how we're quotaing people. And so, there, you can get some things as well where if we're grossing up on partner revenue, you can be hitting your quota from a sales perspective. It looks different from a revenue perspective. It's basically a bookings revenue mismatch in many cases. So that's one of the things at Vercel we've just decided we're going to look at things on a gap revenue basis, just make it simple. Again, I'll have more forecast call, but I'm going to translate that into gap revenue basis when we talk about it as an executive level.

Brett: When you think about company health or health inside of your part of the organization, what is the hardest thing to find numbers to govern?

Jeanne: Product marketing is one mostly in that it is less isolatable. So if you're in charge of both launching and then landing, you've got to work closely with the demand gen team. You're working with parts of sales. That's a little bit of one that maybe you can tie day of launch metrics to product marketing, but that's not why product marketing exists. Brand is another one that certainly has metrics around it, but you're looking, you can do all sorts of awareness studies, but there are certain things that are less immediately quantifiable. Within sales, you got different... How exactly do you determine just how effective your RevOps org is? Typically, there's a little feels of like, are they helping you with throughput? But how exactly would you quantify whether or not you have an A or an A plus RevOps team? I'm not totally sure the answer to that one.

Brett: How do you think about your job as a peer on the executive team? You have your own body of work that you're owning, and you're part of the org and the outputs and outcomes that come of that. And at the same time, you sort of wear this other hat, which is you're one of a handful of a number of people that are kind of governing the entire business, and you're a manager of your exec team and a teammate or peer of this other team. What are your thoughts on specifically when you wear that hat, what you're trying to do to be effective?

Jeanne: I think most folks, if you've done the kind of five dysfunctions of a team, you're supposed to think of your peer set as your primary team. And so, in that forum, I'm meant to help facilitate better outcomes for the company while bringing my functional perspective to bear. But I think that means you're going to wade outside of your functional area pretty frequently. Our chief product officer this morning, I woke up to a lot of feedback on aspects of the sales process. He's just took a couple of sales calls with us, which was great, super motivating for me. There are things where he was wanting to also check, "Hey, I'm newer to sales myself, so just tell me if this is how this works," or "This felt off to me. I think we could do better here." Similarly, I'll go give feedback obviously on a roadmap coming in while we were getting set up here. I was messaging back and forth with CFO about some of the budgeting decisions we might want to be dialing up or down in Q4, sort of given what we're thinking about for FY27 plans. So I think in general, as an executive, you need to be highly accountable to having your function do its job, but you should just be contributing more broadly to what are the set of things that you think are more likely to make the company successful. One of the ways in which I saw this actually work the best, Stripe, sort of late in my tenure there, Stripe got much, much, much more rigorous about, the budget is the budget. We've got headcount OpEx, and that will be the number that we have collectively as a company. Across the course of the year, opportunities would emerge that you would want to fund, and you had this concept of self-solving and would frequently donate headcount, take it out of my P&L, go give it to product because I actually think if they can go do this thing, I'm more likely to make money over here.

Brett: How did that work? Because I think this sort of normal dynamic would be everybody builds their fiefdom, right? A new dollar comes available, and everyone on the exec team is trying to grab that. So what was the dynamic where that was the inverse?

Jeanne: One, you had actually a leadership team at that point that had worked together for quite some time on average. And so, we had built a fair amount of trust. There was a lot of work that Will Gaybrick did, to his credit, to get all of product, go-to-market, finance in sort of the same room. We ran basically a 30-person leadership team for a while, which is a lot to have in a weekly staff meeting, to have on every single offsite that you're doing quarterly was a lot of time with 30 people. But I do think that built a level of trust. I wish I had a more framework-based answer for you, but it literally would be like, I'm in a room with Fran Ryan, John Affaki, they were two of the more senior engineering leaders, and we'd just be like, "All right, guys, this thing's not tracking. I think if I gave you two partnership heads and you put them on that engineering team, we'd actually make that thing bright green, whereas this is not going to really go from red to yellow." And it was truly just some of the better same team functioning that I've been a part of. But again, Fran and I, John and I had worked together for half a decade.

Brett: But is that part of it is just so much at the end of the day depends on the quality of the relationship between a small number of people?

Jeanne: I think it's that, and it's a pattern of people showing up with the best interest of the company in mind. So it's a trust of like, you're demonstrating that you're optimizing for company outcomes and not your own.

Brett: Do you think if you were in the CEO's seat or you have your own executive team, multiple functions, that it's easy to understand who's optimizing for what or it's tricky?

Jeanne: I think it's relatively easy. I did this when... So I changed roles at Stripe seven years in. I moved to run all of our global product partnerships, so everything with like the banks, Visa, Amex, that type of stuff. And so, I came in, and that org had had a fair amount of leadership turnover over an 18-month period and was pretty clearly in need of some org changes. To me, that was a bit of a new function for me. Product partnerships is adjacent to go-to-market. There's a lot of functional acumen I can pull through, but I didn't know anything about how you partner with a bank, et cetera, so I was learning where it wasn't like I could just go take a sales org design and stick it in this context. So basically, I went to that leadership team, everybody agreed our current org design is suboptimal, so that was good. We agree that something needs to change, and I basically said, "I would like to do this change with you all. And so, to the extent that you all are demonstrating that you are keeping your Stripe hat on, we will do this together." I want to be clear that I am the decider. And so, the minute that I think people are putting their own person hats on, then I will make the decisions going forward, and we will stop the collective decision-making here. To that group's credit, everybody did keep their Stripe hat on, and we made very tough calls. I think every single one of my direct reports had their remit changed by close to 50%, so gave half their Legos to someone, kept the other half. All of them, I think, ultimately liked the shape it landed in, but it was one where you can tell when people are doing first principled thinking, using frameworks, taking names off org charts, and just designing, "Here's what's the best outcome, and then sure, we'll put the humans back into it" versus when you have a lot of like, "Well, but this, I feel that. How would this person react," that type of stuff.

Brett: Is there anything else you did to encourage people to behave that way or once you put in the stake in the ground, it sort of took care of itself?

Jeanne: No, I mean, there was a lot of one-on-ones that would happen throughout that so I could understand where each individual was nervous and then use that as ways to go back to frameworks that would help us make decisions. So we had to make a call on, are we going to be partner aligned, functionally aligned or regionally aligned? Those are all rational ways to set up an org. You could make arguments for all of them. So we actually just decided we're going to go and make the case for every single one of those, and then we'll make the case why each of them doesn't work, and then we'll work through it. But if you sort of started by, again, sort of just how would you first principles make an argument for any of these, then that sort of got facts out on the table as much as possible. And then, you could debate how to optimize, but created a solid foundation. It was a lot of workshops, so it was a lot of getting people in the exact same room with a whiteboard and having the space to debate. I think often, we'll do offsites and you try to make something that should take three hours fit in one hour on the agenda. So we did a lot more of that because I think a lot of times, if people can talk through things out loud, then that also makes you less nervous that you haven't been heard or we haven't worked through your concern.

Brett: It would seem that a company utopia would be, you have people that all they do is wear the company hat and they do great work, and over time, the people who are best situated to ultimately be C-level of this or VP of that would be in those roles. My sense is across companies, it never really works that way.

Jeanne: No.

Brett: And there is this sense of you have to advocate for yourself. And then, there's extremes where either self-advocacy gets in front of what's right for the business, so the classic version of that is you get a marginal dollar and you just want to build your fiefdom would be one example. You quickly get into, well, what is politics and politicking? And at scale companies, you have the classic thing, which is the people in a lot of the functions are just the best at politicking as opposed to running the function, whatever. What's kind of your perspective on that? How do you toe the line between advocating for yourself and advocating for the company? Is there a tension in that?

Jeanne: I mean, one of the things, I'm a big believer in your work should speak for itself. I have definitely learned over the course of my career that there have been many times where not purposefully putting more visibility on my work meant that it was less well understood. So I certainly had experiences where my peer set was acutely aware of the work I was doing and its impact. The layer above me was less so because I was not spending a bunch of time doing internal marketing of myself. I think you have to be probably aware of that at larger companies. For me, personally, I just hate it. And so, that often becomes, to me, a time when I debate whether or not this sort of company has scaled beyond what I want it to be for me, personally. I remember actually the moment at Google where I went to business school at Stanford GSB, and they had a class there. It was called Paths to Power. It was basically a class on politics. I did not take the class. I reached a point in my Google career where I reached out to the professor and was like, "Can you send me the syllabus," because I realized I was being outpoliticked by people who were less effective than I was. And then, I never read anything on the syllabus. I decided to leave. I had a little bit of that at Stripe too, which sort of I like being at companies when it's truly intellectually pure. That was actually one of the things that really got me to Vercel was the interview process that I had with the executives who were going to be my peer set was one of the most transparent showed... There's actually a session with the head of people and the CFO that was like, "We are going to spend the next 45 minutes only talking about the warts on this company because if you join, you will be stuck with them, too. And do we want that?" I just had this sense for this was a group of people that were some of the most fundamentally apolitical people I had met, which has been true since arriving at the company. I do a working with Jeanne doc for my orgs, and one of the things in the about me session is I just believe deeply in brutal intellectual honesty. And the definition of that is basically your ability to detach your ego from an idea. So most folks have those very deeply intertwined. You have an idea. I think it's a bad idea. You feel that now, you aren't smart versus I'm very smart. I just had a bad idea. It's actually pretty rare for people to have the level of self-confidence to be able to detach an ego from an idea. I like operating in those types of environments, so I tend to seek them out.

Brett: Is there anything else you do in the part of the org that you own so that great work speaks for itself and as much as you can, all the other shenanigans are sort of kept at a minimum?

Jeanne: Yeah. I mean, I think you do this by how you highlight work, who you highlight. That's often I'm spending my time with the people that I know are doing really great work.

Brett: How do you know they're doing great work?

Jeanne: I normally end up being close to it, and you can see it. I think it's often pretty clear to most people who are the individuals that are doing three to 5X the number of humans. For me, coming into Vercel, you're trying to figure out who are the set of people that are going to give me the most insights, help me ramp, figure things out. In a lot of cases, those people will seek you out, too. I think the way I'll experience the way they interact is also just like very selfless sharing of information. There's clearly no agenda. They are similarly just trying to have a sounding board with you, "Hey, I witnessed this. I've got this insight. What do you think about this" with nothing, what's in it for me versus others. You can tell when people want to get on your calendar to give you some feedback, but they're mostly trying to position it as, "Look at me." I think if you've been in leadership for a while, you sniff that out pretty readily.

Brett: Isn't the opposite of the point true at various points in your career? You made the statement that if you're doing three to 5X the work of the average person, it's clear, but in many points in your career, if you look at a level up from you or two levels up, they weren't aware. It seems that that was you at that point in time. And so, what's going on? Is it just people intentionally sort of trying to make that obscure, or is there something else that it's actually harder to be aware of all of that as an org begins to scale?

Jeanne: I think it was people were always aware that I was a high performer. I think there had been other individuals who were very effective at putting bows on things that maybe other people knew had warts under the surface. And then, one of the potential downsides of being somebody who's pretty brutally intellectually honest is you actually expose all the things you know to not be working. If I'm in a forecast call back in Stripe days and we're struggling on a certain thing, I will talk about all the ways in which this thing is not working. "Here are the things I'm trying to do to fix it." I know the peer next to me has the exact same problem, and sometimes that person instead might be like, "Oh yeah, we got this. We're on top of it. We'll fix it." There's that version of the world of like, "I'm not going to uncover reality to you. I'm going to mostly hope you look over there while ideally I figure it out," versus "I want you to be acutely aware of the things I'm working on so you're not blindsided by it, but you are then going to know that this isn't all perfect on route to getting to hopefully what is the right outcome." Probably, there were points where I should have just put a bow on it.

Brett: You mentioned at various points at Stripe, there was kind of a formal or informal exec team that was, call it, 30 people. That seems very bad. Why did that work, or what was the good parts of that, or how did that end up being for some period of time?

Jeanne: So Stripe had LT, which was basically like John and Patrick's directs. It had OG, which was basically more or less the directs of those directs. And then, it had GPTL, which was go-to-market, whatever. It was go-to-market and product. I always like invert some of the letters, too. And so, it was basically born out of as Stripe had gone through hyperscale. We had lost some of the connectivity between GTM and EPD. And so, mostly, it was actually to bring those groups together, squash them together and be like, "We will be one team because right now, we are operating as two functions." And then, you also had finance and some other folks in there that would make everything work together more effectively. So it was more like these were the core operating groups of the company and that we needed to get to that, sort of overcome the five dysfunctions of a team to be like, "This is your team, not the go-to-market org, not the EPD org."

Brett: And so, how was the time spent? How do you have that number of people-

Jeanne: Yeah, I mean, so-

Brett: ... do anything productive?

Jeanne: ... I think anybody who is in those forums will tell you there are things that worked and things that didn't. So things that worked was at least everybody did have shared context. You were in the room. Things that didn't work was with 30 people in a room, probably 10, if that, are going to take up the majority of the air time, and the 10 who did weren't always the 10 who likely should have. I think there were times where you weren't getting to the right answer efficiently or the people who really should have been weighing in were being silent just because of how they wanted to participate, so that was a bit of a challenge. It was a lot of time, I mean, hours and upon hours every week together, so it was a real commitment. I do think we did really turn a corner as far as operating as a same team. Yeah, and I don't know that we would've gotten there without that level of forcing function. So it was an expensive investment, but I would argue it paid off in the end.

Brett: So how do you spend your time in a given week? And maybe if you think back over the last few months, what are you sure is the correct attention you're spending in a given week? And are there areas where like, "Ugh, I really feel like it should be optimal for me to do X or Y, but I haven't sort of done that yet"?

Jeanne: I don't necessarily have a framework per se of like, "I'm going to spend 10% time of this, 30% of time on this, et cetera." This is not a week by week thing, but I tend to have one to two quarter periods that are more internally focused versus externally focused. So often, I'll realize there are a set of things that are not functioning about an org, and then we'll have a period where I'm going really deep on our core operations. Do we have the right org design? Do we have the right ways to look at the business? Do we have the right set of initiatives? And then, you sort of get that foundation set, and then now, you can be much more externally facing. I'm doing a lot more sales calls, getting back squarely in the market. I find it's hard to do both of them equally at the same time. That's sort of one way for me that things tend to ebb and flow. I find one of the things that I have to keep myself honest about is carving out time for deep thought and more of long-term thinking. It's extremely easy for that to get scheduled over. Plane flights are my favorite these days.

Brett: But now with Starlink, it's going to be less effective to disconnect.

Jeanne: Yeah, yeah. Yeah, there you go. Anyway, I mean, that's sort of the number one thing I have to check myself on is my job is not to be triaging every day. It is very easy to triage every day. It tends to be that when I do things that have the most impact on the org, it has been because I have taken time out to go have deep thought. Also, there are certain themes in a quarter where I'm particularly trying to move the needle on in that more hands-on way. A great example of this right now is as Vercel becomes more of this platform, we need to be better at selling to executives, and that's a hard muscle to build if you've been selling to developers. And so, I am spending a lot of my time right now personally doing that. So we need our SDR team out prospecting to executives and getting comfortable with that. So Guillermo and I currently have a contest on who's going to be the top SDR at the company. So he's beating me actually on the founder outreach to startups. I'm probably winning in enterprise CXO outreach, but I'm personally doing that and taking a lot of the first calls so that I can figure out exactly what should we say. And then, people can listen to my Gong calls and hear, "Okay, what did you do? How would I emulate that?" So that's a top of mind thing where I'm super in the weeds right now as we sort that out and build the muscle.

Brett: When you build a new capability, if you go back to Stripe and you're operating at mega scale, order of magnitude maybe more than where you are today, do you still believe that the exec should basically be inventing on their own or just doing the thing first?

Jeanne: I do think so. At Stripe, we would update our core narrative, and I would be super in the weeds with typically some of our best sales leaders, best AEs, product marketing that was figuring it out, coming up with that deck. I'd be dry running it. I'd be the person that you would record the video for folks to listen to. I'd be the one delivering it. I think that's important in having connectivity to your org and to the market. More recent example that was at Stripe was we were trying to drive a pretty different partnership motion with some of our payment method providers. So that was another one where I was like super... At one point, I think I mocked up how you would change the UI, which I'm not a product manager, but I saw this great commercial opportunity from a partnership perspective, was trying to go pitch product that we should invest in this and went out and did that, got the buy-in as a result of that. And then, we drove an 18-month long massive initiative across changing product, huge partnership motions, et cetera.

Brett: The topic of execs, one of the things that comes up all the time is the person was great at X scale, but they couldn't scale, so they got us to 100 million and then they couldn't scale. When someone says that in your experience, what do they normally mean? Where do people struggle to uplevel or grow?

Jeanne: I think it's in two ways. So either one is they fail to scale their people leadership, so going from frontline management to second line to third line because each of those does require a different way of operating. So that's one area. And then, the other is actually typically the business changed and you didn't adapt your skillset to that. So a great example of this, it would be like companies that are scaling revenue. Typically, you start in one segment and you wind up needing to be in another. So a lot of them will start with the PLG-heavy inside sales type motion, and then that sales leader, as an example, cannot scale when you start doing big enterprise deals. I think that's where people get more stuck is I couldn't acquire the incremental functional acumen or hire under me such that somebody brings that in and shores up that weakness for me. And as a result, you become a rate limiter on the org's ability to perform.

Brett: If someone's effective at 25 million in ARR as some simple proxy metric and their goal is not to be layered or managed out and they want to get into hundreds of millions, again, in this fictitious example, are there things they should be doing or ways they should be spending time or investments they should be making in some marginal unit of time that will increase the chance that they can be in the seat for longer?

Jeanne: Look, you can say, "Go read a lot of books. Go try to learn things." I actually think the best piece of advice I ever got that stuck to me is that you need to work yourself out of a job, which is as you're scaling, you're comfortable doing the job you have become good at. But if you keep doing that job, that is no longer the job at 100 million versus 25 million. And so, I think that the minute you feel you have deeply mastered something is probably the point at which you should be figuring out how somebody else does that. So either you're teaching it to somebody below you who is going to be able to move in and take that off your plate, or you're starting to think about how do I hire for that so I now have the bandwidth to go learn the next thing.

Brett: So a way to think about that is the CRO. The dominant motion is PLG. That's kind of your jam. You came up through that. You want to get out of the PLG business in short order and start working on the other part of the business. Is that sort of what you mean?

Jeanne: Yeah, because you should if you've got expertise there. Sort of like we were talking about earlier, you ought to be able to now know where to poke pretty easily. You did that job, so if somebody else is doing it for you, you're going to have more comfort and handing that off and then being able to monitor, and then you can go invest in the new place. And then, I think you just have to have self-awareness of when you are climbing that learning curve effectively yourself versus when you need to bring in additional expertise. I mean, I'll give you an example at Stripe. My sales career path started in PLG also. The first sales team I ever ran was sold into the less than 50 employee segments, so that's real small. And over the course of subsequent roles, I kept having an opportunity to move up market, and Stripe started to move more squarely into enterprise. There are a bunch of ways in which I had been effective at picking that up, had been involved in a lot of our early deals, made the case for getting into enterprise to the board, but enterprise sales leadership is a skill that's learned over decades, period. When we got serious about we are now going to go from, we had the enterprise tiger team, so our sort of seven first figure it out reps to actually know we're now investing in enterprise and we're going to have multiple managers here was when I went out and said, "Okay, it's time for me to bring in an enterprise leader who is somebody that I will learn from while we continue to scale this organization."

Brett: When you zoom all the way out and you think about ending up sort of in this COO role, if you remove anything related to the genetic lottery and you remove anything related to good luck and you try to figure out what were the controllable inputs for you in your career, what do you distill it down to?

Jeanne: I very purposefully followed high-quality leaders. So Claire Johnson, a lot of people know, I worked for her three times. Another gentleman, Rich Rao, I worked for him twice. I worked for him before business school. I came back from business school explicitly to work for him because I felt he was somebody I could learn from. In both of those cases, those were individuals who I not only felt I could really learn from and who were invested in teaching me, but they were also clearly people who were driving exponential growth for their own careers that then if I'm adding value to them, they're pulling me along with them. So I think I was very thoughtful about who I worked for. I was somebody who always did value depth, and I think people are willing to take risks on you when you are definitely good at certain things, right? So they're like, "This job description has five major things. You clearly are quite good at three, so I feel confident you'll go figure the other two out." That was frequently the story of my career. I did a stint in APAC at Google. I knew nothing about the region. I was going to manage both SMB and mid-market. I did not know mid-market, but I had done a lot in the year prior to sort of be like, again, you'd check half of the boxes on that resume. Same thing happened at Stripe when I moved into partnerships. I actually remember having a conversation. That job, at the time I accepted it, rolled into the CFO, and I remember having a conversation with her that was explicitly, "I've looked at the job description for this. I checked half of the boxes and I don't on the other half, but I think given my Stripe experience, hopefully, you can believe I'll get there." I do think the third, we've talked about it a lot, is just being somebody who's known for trying to make an organization better. And so, a lot of people root for me because I've typically helped them be better at their job too.

Brett: Is there a formal or informal performance review that you've had in your career that was the most valuable?

Jeanne: I have had quite a few that have stuck with me. I don't know that this is the most valuable per se, but it's definitely the one where I left the review and I certainly will never forget it. So I reported to John Collison for an interim period. I had one performance review with him, and one of the things he said to me was going back to the conversations we had on being demanding and supportive. He said, "Within your own organization, you do a great job of being both demanding and supportive. Cross-functionally, when you don't think somebody's good at their job, they're dead to you." And that phrase, you can't unhear that. That's not very flattering, which of course, I went home, and I was like, "What is he talking about?" And then, I slept on it, and I was like, "I actually think that's a completely fair comment." And then, I saw myself doing that very frequently of completely writing somebody off when I did not think they were effective at their job in a function that I was not running. I don't know that I have fixed that, but I am now far more self-aware.

Brett: I still write them off, but I know that I'm doing it.

Jeanne: I really try, and I actually think being in this role of a COO, because I've got this many more functions, is you just develop a lot more empathy of like a lot of times when you think someone's not doing well, it's because you don't have visibility into how their functional sausage is made, and the fact that it's actually hard to produce the output from you on the outside in maybe looks a little bit more straightforward. So I do find, over the course of my career, I've developed meaningfully more empathy through various points of either failure or relatively harsh feedback.

Brett: What about on this theme of things you've had to figure out or actual skill development versus sort of innate parts of you? When you think about becoming a C-level executive, if you sorted everything you had to figure out over multiple decades, are there a few things that are both the most important and the hardest from an actual, "I needed to develop a competency in this standpoint"?

Jeanne: I chose to go to business school because I thought I did not have enough hard skills. I was a French major, and I went to Google and the role that I was in and support at Google was great at teaching you how to get things done, and influencing without authority was something I really learned, but I was not facile with a spreadsheet. And so, I went to business school specifically because I did not feel like I could understand P&L effectively, could use data effectively. So that was sort of my crash course in hard skills. Other ones have been more around like leadership development. Google really had pretty exceptional leadership development training during the years that I was there, which thanks to Sheryl Sandberg. There are a lot of those that were hard. I remember one. Claire made me cry at in front of 15 people, which was another one that leadership development, how you influence, how you show up, et cetera. But there were a lot of those that I think shaped me a fair amount as a leader and how you scale and get people on board.

Brett: Maybe just to wrap up on sort of a similar vein, who's the person that's influenced you most in the role of an exec and what's the most tangible thing they imparted on you?

Jeanne: I'll answer this two ways. I do think Claire had the most influence on me in how I show up as a people leader. I was always really impressed by how she got cross-functional groups of people together and aligned around a common goal. She stepped out of her swim lane so beautifully and was somebody who always, I think, was trying to facilitate honest dialogue to get good answers. So I definitely credit her with a lot of things I looked up to from like a how perspective. I think from a content perspective, because I do pride myself on being a leader who isn't just a general athlete, like I'm not in an executive role because I have leadership skills, I'm also in executive role because I really do have functional depth. And that actually, I think, was more self-initiated, and it was basically my experience going out to APAC and being like, "Oh, I now manage a bunch of sellers who have sold for a decade, and I've never carried a bag, and they have skills I don't have, and I had better go learn them real quick so that I can be credible." And that was sort of the moment where I was like, "Okay, sales is a functional skill, and depth at that is differentiating as well."

Brett: Good place to end.

Jeanne: Yeah.

Brett: Thank you so much.

Jeanne: Thank you.

Brett: I really appreciate it.

Jeanne: Yeah.

Brett: That was great.