Channel
Interviewed Person
Jeanne Grosser
In the first Executive Function episode, Brett sits down with Jeanne De Witt Grosser, Chief Operating Officer at Vercel. Before Vercel, Jeanne spent nearly a decade at Stripe, where she built and scaled global revenue teams and led product partnerships. In this conversation, she unpacks what separates good executives from extraordinary ones, shares her rigorous executive hiring process, and reveals the brutally honest performance review feedback she'll never forget. In today's episode, we discuss: • What it takes to operate at 30,000 feet and ground level simultaneously • The leap from frontline manager to manager of managers • Inside Jeanne's executive interview process • The inherent value of driver trees for metrics • Why context is everything References: • Akamai: https://www.akamai.com/ • Claire Johnson: https://www.linkedin.com/in/claire-hughes-johnson-7058/ • Culture Amp: https://www.cultureamp.com/ • Guillermo Rauch: https://www.linkedin.com/in/rauchg • John Collison: https://www.linkedin.com/in/johnbcollison/ • Next.js: https://nextjs.org/ • Nike: https://www.nike.com/ • OpenAI: https://www.openai.com/ • Patrick Collison: https://www.linkedin.com/in/patrickcollison • Stanford Graduate School of Business: https://www.gsb.stanford.edu/ • Stripe: https://www.stripe.com/ • Vercel: https://www.vercel.com/ Where to find Jeanne: • LinkedIn: https://www.linkedin.com/in/jeannedewitt Where to find Brett: • LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ • Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: • Website: https://firstround.com/ • First Round Review: https://review.firstround.com/ • Twitter/X: https://twitter.com/firstround • YouTube: https://www.youtube.com/@FirstRoundCapital • This podcast on all platforms: https://review.firstround.com/podcast Timestamps: (01:17) What separates good executives from extraordinary one (02:48) How leadership changes as companies scale (04:15) What an executive is actually accountable for (06:11) The leap most rising leaders never make (07:52) When to dive deep vs. when to step back (10:09) Teaching people to think like you do (11:56) Creating a shared language across the business (13:52) What a COO job description actually looks like (17:20) The upside of owning the full customer experience (19:10) Why marketing rolls up under a COO (21:06) Being demanding and supportive at the same time (22:33) Inside the executive interview process (27:35) The workshop prompts that reveal everything (30:11) The common thread in failed executive hires (36:36) Metrics: the driver tree philosophy (43:04 What a collaborative exec team looks like (57:08) How Stripe got 30 people to operate as one team (1:03:50) Working yourself out of a job (1:10:32) The review feedback you can't unhear

First Round Capital
Interviewed: Guillermo Rauch

First Round Capital
Interviewed: Guillermo Rauch
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? Some of what I would say is, and this was 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 ft and ground level. So, from a 30,000 ft 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, >> just given the amount of change. >> Yeah. with AI like I you just don't really have a sense for if I put together a two-year plan is that reasonable. So I I I think that's one and then at the same time you're 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 ft view and what needs to be true to realize it. And not everybody at your company has had the experience before to know how to go and say, "Okay, well, this was Jean's northstar. I know how to turn that into an hour by hour, minuteby minute operating reality." And so you're in some cases building that yourself. Uh you're in other cases coaching somebody
who's, you know, has the 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. >> 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, a,000 5,000 10,000 does that change pretty dramatically or do you think it's somewhat similar? >> I think there are parts of it that are similar. So you know when I was at
Stripe we were I think 8,000 people by the time I left. Um, Verscell 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 I'm going to get in there almost like an IC alongside the working group. I think like as a as
a company scales, if you've done a good job of hiring, you do have more people that you can give a northstar to, give a set of metrics to, and like you don't have to be in the nuts and bolts of that thing. So it's a bit more maybe of like an altitude question, but it doesn't change the fact that as an effective executive, there are set of things where you're going super deep either personally doing the work or deeply deeply reviewing it, you know, and then a set of other things where you're have confidence that the team's going to go execute without you being super close.
And maybe if you take a snapshot across a couple of the points in your career in sort of the different executive seats, what is the outcome that you are responsible for? You know, it's 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. I mean, you spent a decent chunk working on different parts of the revenue or 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. It's a sort of
multi- 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 tenurs. Hopefully Verscell will be a third for that. Um and so executives have decadel long stints because you are able to replicably produce results year after year after year. And so that means you need to be you know the bulk of your team is going to be focused on executing for inear results whether that's in