“I think there's a direct correlation in onboarding with sellers that are annoying and sellers that are not. And when I say sellers that are annoying, they are constantly asking questions 24-7. … There is a direct correlation with that person being incredible. The inverse is not always true, but I think the folks that are quiet, not asking any questions or asking questions that any AI bot or Notion bot can answer, usually that's going to be weak signal.”
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · Startups & Venture · October 2026
Freeman, who runs sales at Ramp, was asked how quickly he can tell that a new hire isn't going to work out. His test is how much they pester him in their first weeks, with account strategy, pipeline and product questions. He adds that he leaves at least ten minutes of every interview for the candidate's questions for the same reason.
Transcript
…on the segment. Our down market sellers inside sales rep 60 days. Commercial reps, 90 days. Mid-market, four months. Enterprise, five months. And our strategic enterprise is a six-month ramping schedule. The reason why those ramping schedules exist in that way is just due to cycle length timing.
How quickly do you know if someone's not very good? I
think it's actually fairly simple to get a pulse check on if someone is going to be good or not. I think there's a direct correlation in onboarding with sellers that are annoying and sellers that are not. And when I say sellers that are annoying, they are constantly asking questions 24-7. They're very thoughtful. They're talking about account strategy. They want to pick your brain about pipeline and getting you to send emails on their behalf. They want to ask you product questions and it's never ending. There is a direct correlation with that person being incredible. The inverse is not always true, but I think the folks that are quiet, not asking any questions or asking questions that any AI bot or Notion bot can answer, usually that's going to be weak signal.
I totally agree. I always say actually the quality of a founder is very obvious. The quality of the questions a founder asks at the end of an interview with a VC or a meeting.
That's why I intentionally leave at least 10 minutes in an interview for them to fire away at me.
Because it tells you, people think, like, my partners will often say, why, why are we spending so much time answering that question? Because you don't get it. I'm actually measuring them. They go, tell me, you've got four partners. Is it an equal vote in the IC? Or how do you guys think about…
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