M
Matt Wensing
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Jul 24, 2026
EP107 From Founder to VP: What Changes About Product Judgment at Scale
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32:06

Jay StansellHOST
To go into then someone else's vineyard and produce wine for someone else, How do you either consume their standards and recalibrate yourself or how do you bring in your own standards and get them to recalibrate? What does the tactics, the play, the mindset look like to do that in a way that is obviously sensitive to your point, the velocity of progress and decision making, but also whilst either reflecting on the existing standard or asking those around you to respect the new standards? What does that look like as an approach?

Matt WensingGUEST
The company matters a lot, so I would say start with an understanding of what kind of company am I in.

Matt WensingGUEST
My first company was bootstrapped for a while, then it was VC funded, and then ended up being private equity owned.

Matt WensingGUEST
Very different companies in terms of the DNA, the culture, who gets to establish the taste.

Matt WensingGUEST
What environmental factors, including the market, are dictating our taste? Are we hell bent on being the fast follower of this market leader and therefore our tastes, all of our cues are gonna come from that.

Matt WensingGUEST
So you really need to get your bearings in terms of what kind of company am I in? Now, Customer.io is the kind of company that was founder built and led, I would say bootstrapped and then fund strapped.

Jay StansellHOST
What mechanisms, what tactics, how do you stay in touch with the decisions that have been made around you knowing that you're not the one making those decisions or being across all of them all of the time? How do you stay in touch with that and how do you ensure that you can operate as a VP knowing you're not in the room for every decision? But a lot of time you could be accountable for some of those decisions regardless.