Executive Function: Building systems that can make decisions without you | Jeanne DeWitt Grosser (COO, Vercel)
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Episode: Executive Function: Building systems that can make decisions without you | Jeanne DeWitt Grosser (COO, Vercel)
Pub date: 2026-02-05
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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 ones
(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
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