Feb 5, 2026 · 1h 14m · in-depth
Executive Function: Build systems that can decide without you | Jeanne DeWitt Grosser (COO, Vercel)
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In this masterclass on executive leadership, Vercel COO Jeanne DeWitt Grosser explains how top leaders operate simultaneously at strategic and operational altitudes. She shares actionable frameworks for cross-functional alignment, executive hiring, metric governance, and scaling high-performing organizations.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Brett holds 15.6% of the talking time here. How this is scored →
Brett as informed peer 4.5 Guest teaching 6.7 Guest disagreement 1.2 Brett pushing back 2.0
speaking balance: gold is Brett, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 54:40 Pushing back on the assumption that high output is universally visible
Jeanne counters Brett's suggestion about workplace transparency by detailing how political individuals put bows on broken systems while intellectually honest operators expose their own flaws.
Hardest push from Brett ▶ 56:02 Brett challenging the viability of large executive forumsBrett directly challenges Jeanne's description of Stripe's 30-person leadership team, labeling it as seemingly terrible and demanding an explanation for how it could function.
Biggest teaching moment ▶ 33:40 Why functional expertise is required to direct AI workflowsJeanne breaks down the mechanics of prompt engineering and GTM automation, demonstrating why twenty years of sales judgment caught critical nuance that a top SDR and an automated agent missed.
Brett holds their own ▶ 27:35 Brett identifying interview pre-calls as the highest signal stepBrett introduces his own strong operational conviction on executive interviewing dynamics, validating and advancing the interview case study framework.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Brett as informed peer | Guest teaching | Guest disagreement | Brett pushing back | Why |
|---|---|---|---|---|---|---|
| Balancing 30,000-Foot Strategic Vision with Ground-Level Execution | 4 | 6 | 1 | 2 | Brett opens with a focused question about what separates good executives from extraordinary ones across scaling stages. Jeanne provides deep operational framing on operating simultaneously at 30,000 feet and ground level, which Brett prompts her to unpack further across different headcount stages. | |
| Executive Responsibility, Multi-Year Horizons, and the General Manager Mindset | 4 | 6 | 1 | 1 | Brett asks what specific outcomes an executive is responsible for across multi-year tenures. Jeanne reframes the role from hitting short-term quotas to acting as a general manager who creates replicable systems and looks holistically across cross-functional roadmaps. | |
| Overcoming Scaling Ceilings Through Systems Thinking and Shared Mental Models | 5 | 6 | 1 | 3 | Brett pushes Jeanne on the tension between delegating through systems and diving deep into operational details based on his knowledge of Stripe culture. Jeanne clarifies how staying close to top frontline performers and driving early project velocity creates a shared mental model. | |
| Establishing Common Operating Frameworks and Navigating Product-Market Fit Disputes | 4 | 7 | 1 | 1 | Brett asks for specific examples of operating mechanisms and where shared context is hardest to build. Jeanne details lead-to-revenue models and dissects the tension between GTM and engineering over product-market fit in enterprise segments. | |
| Defining the Chief Operating Officer Role and Managing Scaling Culture | 4 | 7 | 2 | 2 | Brett asks Jeanne to define the COO role from a blank sheet of paper and challenges how cultural changes are evaluated. Jeanne gives a pragmatic definition of the COO role as owning what the founder does not want to manage while orchestrating company-wide operational alignment. | |
| Unifying the Customer Journey: Aligning Brand, Demand Gen, and Go-to-Market | 5 | 6 | 1 | 3 | Brett presses on the potential downside of consolidating marketing under the COO at a founder-led, brand-centric company like Vercel. Jeanne explains the rationale of unifying the full revenue engine while leaving brand oversight directly accessible to the CEO. | |
| The High-Support, High-Demand Management Philosophy and Executive Interview Architecture | 4 | 7 | 1 | 1 | Brett inquires into Jeanne's management approach and interview structure for senior leaders. Jeanne details her multi-stage interview funnel, explaining how upfront radical transparency filters out misaligned executive candidates. | |
| Evaluating Executive Practicality Through Real-World Case Studies and AI Prompts | 6 | 6 | 1 | 2 | Brett adds his own experience regarding interview candidate pre-calls, noting how question asking offers high signal. Jeanne agrees and explains the practical prompts she uses for CRO candidates, including real enterprise scenarios and AI integration. | |
| Identifying Executive Pitfalls: Contextualization Failure and Cultural Inadaptability | 4 | 7 | 1 | 2 | Brett asks why failed executives fail and whether the interview process successfully catches those issues. Jeanne outlines the core traps: playbook transplantation without contextualization, lack of cultural adaptation, and inability to build cross-functional trust. | |
| The Crucial Role of Functional Depth in Directing AI-Driven Workflows | 5 | 7 | 1 | 1 | Brett asks whether star executives need to have been top individual contributors. Jeanne illustrates how functional depth is critical in the AI era by describing how her two decades of sales nuance improved an automated AI agent beyond what a frontline SDR could program. | |
| Metric Governance: Utilizing Driver Trees and Standardizing Metric Definitions | 4 | 7 | 1 | 2 | Brett asks what makes metrics tricky to govern as a company scales. Jeanne details the utility of driver trees and emphasizes establishing unequivocal, standardized metric definitions across GTM, finance, and product to prevent siloed debates. | |
| Executive Peer Dynamics, Budget Self-Solving, and Company-First Collaboration | 4 | 7 | 1 | 2 | Brett queries how executives avoid building organizational fiefdoms when allocating resources. Jeanne explains Stripe's concept of self-solving and voluntary headcount transfers built on long-term peer trust. | |
| Principles of First-Principles Org Design, Self-Advocacy, and Brutal Intellectual Honesty | 5 | 7 | 2 | 3 | Brett pushes on the reality of corporate politics versus pure meritocracy and asks how to balance self-advocacy with company interests. Jeanne shares how she navigated organizational redesign from first principles and her core philosophy of brutal intellectual honesty. | |
| Navigating Communication Transparencies, Large Leadership Forums, and Executive Time Alloc | 5 | 7 | 2 | 4 | Brett challenges the efficacy of a 30-person leadership meeting as inherently unwieldy and points out the tension between high performance and visibility. Jeanne explains the specific trade-offs and forcing functions that made the setup work during hyperscale. | |
| Career Progression, Working Out of a Job, and Formative Executive Influences | 4 | 7 | 1 | 1 | Brett explores executive scaling ceilings, career progression inputs, and impactful feedback. Jeanne shares formative career lessons, including John Collison's pointed feedback on cross-functional collaboration and the imperative to continually work yourself out of a job. |
Statements from this episode (20)
Grosser: Vercel headcount exceeds 600; Stripe reached 8,000 before departure
“When I was at Stripe, we were, I think, 8000 people by the time I left. Vercel is now north of 600.”
Grosser: Transitioning to second-line manager is one of leadership's biggest leaps
“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 gotta learn to delegate and get comfortable with that, but you're gonna, you know, seven direct reports on average, like, …”
Grosser: Direct reports should independently mirror the executive's decisions 90% of the time
“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 Ask yourself that question and come up with the answer I would have come up with had I been there alongside you.”
Grosser: Personally leads customer onboarding sessions for every new Vercel hire
“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…”
Grosser: Early enterprise wins lead product to blame sales and sales to blame gaps
“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 pr…”
Grosser: Claire Hughes Johnson managed People before marketing at Stripe
“If you took Stripe under Claire, She had people, but didn't have marketing at the outset, had marketing at a later point.”
Grosser: COO role is whatever crucial functions founders choose not to manage
“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.”
Grosser: Great founder brand marketing alone cannot build a predictable revenue engine
“A lot of founders, Guillermo's a good example, John and Patrick were examples of this well, are like excellent brand marketers, but that does not a predictable revenue engine make on its own.”
Grosser: Laying out real problems in first interview tests candidate motivation
“Mostly telling you these are the problems that, this is the reason I'm hiring your role. I have the following issues that you will need to come and resolve. And I find that by putting those things out on the table in the first meeting, basically, you get a sen…”
Grosser: Strong executive candidates teach interviewers new mental models early on
“Typically, I have learned something. I have learned multiple things. Yes. You know, often, Early, like, you know, 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 imme…”
Grosser: Nike self-hosts Next.js on Akamai rather than using Vercel
“Nike's on Next.js. They're not on Vercel. They, you know, have Akamai as their CDN and WAF.”
Grosser: Vercel is not yet excellent at executive selling
“We are not yet excellent at executive selling”
Grosser: Vercel CPO participates in every executive interview loop to ensure alignment
“Tomo, 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.”
Grosser: Vercel deployed AI lead qualification agents matching human SDR performance
“I launched a GTM engineering team in the first six weeks on the job at Vercel. So basically, we took Three sales engineers were like, congrats, you're now founding members of our GTM Eng team, where we're gonna go bring agents to bear across everything in GTM.…”
Grosser: Vercel's revenue growth model was most sensitive to ACV
“When we did the lead to revenue model, it, 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.”
Vercel standardizes on GAAP revenue for executive-level business reviews
“So that's one of the things in at Vercel we've just decided We're gonna look at things on a gap revenue basis. Just make it simple. Again, I'll have my forecast call, but I'm gonna translate that into gap revenue basis when we talk about it as an executive lev…”
Grosser: Stripe executives donated headcount across P&Ls to self-solve budgets
“Stripe got much, much, much more rigorous about the budget is the budget, like, the, we've got headcount OpEx, and, like, that will be the number that we have collectively as a company. And across the course of the year, opportunities would emerge that you wou…”
Grosser: Stripe ran a 30-person leadership team across product, GTM, finance
“There was a lot of work that Will Gabrick did, to his credit, to get all of product, go-to-market, finance in sort of the same room. Like, we ran basically a thirty-person leadership team for a while, which is a lot to have in a weekly staff meeting, to have i…”
Grosser: Vercel CEO and COO compete in outbound SDR cold-prospecting
“So Guillermo and I currently have a contest on who's going to be the top SDR at the company. So, you know, he's beating me actually on, like, the founder outreach to startups. I'm probably winning an enterprise CXO outreach. But, you know, I, I'm personally do…”