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Jessica Fain: commitment

22 Mar 2026 Lenny's Podcast The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack)

“If you have something net new that you want to bring to market and customer success thinks it would really accelerate expansion rates, or the marketing team thinks that signups would be 10X because of this, if you have that cross-functional alignment, and this is where a lot of these lessons don't just apply if you're going into a product executive meeting, but that if you're influencing your cross-functional execs and your cross-functional stakeholders to be advocates on your behalf, I think that we now have more tools than ever to, as product folks, build out the V1, prototype something, build your own app, build the messy version of it, get feedback, iterate, and be socializing that in a way that creates a groundswell of buy-in to the point that the exec can't say no to the funding.”

— Jessica Fain

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Speaker
Jessica Fain
Attribution
Verified speaker
Claim type
commitment
Recorded
22 Mar 2026
Publisher
Lenny's Podcast

Transcript context

…Like if you were in charge of a company, you'd be so excited if someone came to you with a 10X idea that's going to change the trajectory of your product. That's what everybody wants. And so that is a really powerful way of approaching all these things. Obviously not every idea is going to be a big idea. Not every idea is a great idea. A lot of times these take time also. Maybe speak to that. Just like say you have a big idea and they're like, "Nah," what are some expectations to set for people that come up with a big idea that just isn't getting any traction? It really depends on what kind of organization you're working in. If you're working in a smaller organization, if that big idea is something that you can build on your own or you can build within, versus if you need a large scale investment ... I think the real thing about building toward a big idea, towards something net new, the key is really outside and around the executive. So if the executive is the decision maker on whether we're going to invest here, they also want to understand from their peers, from other experts, why this actually matters. If you have something net new that you want to bring to market and customer success thinks it would really accelerate expansion rates, or the marketing team thinks that signups would be 10X because of this, if you have that cross-functional alignment, and this is where a lot of these lessons don't just apply if you're going into a product executive meeting, but that if you're influencing your cross-functional execs and your cross-functional stakeholders to be advocates on your behalf, I think that we now have more tools than ever to, as product folks, build out the V1, prototype something, build your own app, build the messy version of it, get feedback, iterate, and be socializing that in a way that creates a groundswell of buy-in to the point that the exec can't say no to the funding. Along those lines, it feels like to me, the biggest reason that a leader doesn't buy into your pitch is you just have different information. They don't see what you see, you don't see what they see. They have all this other stuff that they're looking at and trying to decide. Maybe speak to just that skill of trying to clarify information on both sides.…

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