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Tom Verrilli: preference

2 Aug 2026 Lenny's Podcast This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)

“Because you got to ask yourself, do I really want to spend my whole time having this discussion and this debate? But I like being a CPO or a product lead because in a lot of ways what I'm doing is I'm helping translate that vision and that intuition into reality.”

— Tom Verrilli

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Everything needed to verify it.

Speaker
Tom Verrilli
Attribution
Verified speaker
Claim type
preference
Recorded
2 Aug 2026
Publisher
Lenny's Podcast

Transcript context

…Say somebody is looking for a CPO role or a first PM role, they're kind of similar, basically working for a founder. What would be your advice for them to land in a place where they're happy and not just super frustrated by this kind of middle layer where they just don't actually have any agency? Yeah, I mean, I think the first thing you've got to work out is why do you want it? There's this idea that the CPO's job, you get to decide all the roadmaps and all those things, and I've got bad news for you. That's not strictly true. But I think it also comes down to spending some time with that person to work out how do we jam on a topic? How do they like to get pushed? How do they not? And then you spend a lot of your time calibrating. So before I joined Whatnot, I think Grant and I had five or six different coffees where we talked about how do you get this type of team to move? How do you work on those things? And then I obviously went through a series of interviews, and actually came down to LA where Grant and Logan were based at the time, and spent a whole day with them just in a room, going through a couple different problems, talking through different things in the roadmap, just really getting into it. And I tried through that to be my most ordinary self as opposed to interview self, if that makes sense. Because you got to ask yourself, do I really want to spend my whole time having this discussion and this debate? But I like being a CPO or a product lead because in a lot of ways what I'm doing is I'm helping translate that vision and that intuition into reality. And then there is an art to learning how to push somebody without competing with them. And I think a lot of the times I've seen the CPO CEO relationship go badly. It ends up with the CPO is competing with the CEO for vision and they end up at loggerheads. And I think that's not your job. I want to ask more about that, this art of pushing back and nudging things in a direction. Is there one trick or one tip you might share with folks to be good at... Because a lot of people deal with execs and they're always trying to get them to agree to what they want.…

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