“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 sense pretty rapidly for does that person get motivated by solving those things or not.”
quote is from the automated transcript, cleaned for reading:
filler sounds and stutters are removed, nothing is rephrased. names can be misheard
(the analysis reads context, assessments check outside sources). how →
More from Jeanne DeWitt Grosser
Insight
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“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.”
Jeanne DeWitt GrosserFeb 5, 2026▶ 18:41Executive Function: Build systems that can decide without you | Jeanne DeWitt Grosser (COO, Vercel)
Disclosure
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“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.…”
Jeanne DeWitt GrosserFeb 5, 2026▶ 33:14Executive Function: Build systems that can decide without you | Jeanne DeWitt Grosser (COO, Vercel)
Disclosure
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…”
Jeanne DeWitt GrosserFeb 5, 2026▶ 43:22Executive Function: Build systems that can decide without you | Jeanne DeWitt Grosser (COO, Vercel)
AssertionNot checkable as stated
Grosser: John Collison said cross-functional colleagues she doubts are "dead to her"
“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.”
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Insight
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, …”
Jeanne DeWitt GrosserFeb 5, 2026▶ 5:53Executive Function: Build systems that can decide without you | Jeanne DeWitt Grosser (COO, Vercel)
Insight
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.”
Jeanne DeWitt GrosserFeb 5, 2026▶ 8:53Executive Function: Build systems that can decide without you | Jeanne DeWitt Grosser (COO, Vercel)
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