Grosser: Vercel CEO and COO compete in outbound SDR cold-prospecting
Jeanne DeWitt Grosser · Executive Function: Build systems that can decide without you | Jeanne DeWitt Grosser (COO, Vercel) · Feb 5, 2026 · at 1:00:48
Jeanne DeWitt Grosser is the COO of Vercel. She explains how she and CEO Guillermo Rauch are training the company to sell to enterprise CXOs by acting as frontline SDRs.
0:00 / 0:23exact quote · 23.5s
▶ Watch the full episode on YouTube → 720p mp4 · rendered on demand · StarZero watermark
“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 doing that and taking a lot of the first calls so that I can figure out exactly what should we say, and then people can listen to my gong calls and hear, okay, what did you do?”
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
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: 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: 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: 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.”
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.”