Why Leaders Stall When Scaling the Business

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