“When a startup is competing against a large competitor, they aren't competing with the entire company, they are likely competing with some PM focused on internal politics/career progression. With this framing, it shouldn't be surprising to see startups win as often as they do.”

Dalton Caldwell Digital music entrepreneur; Managing Director at Y Combinator

Competing With One PM

From a LinkedIn post by Dalton Caldwell, February 2024.

It is a category mistake to call the PM a competitor. The PM is not trying to beat the startup; they’re trying to get promoted. The path runs through internal politics, performance review packets, and cross-team alignment. The startup and the PM are chasing different prizes.

Steven Kerr’s 1975 Academy of Management paper called this the folly of rewarding A while hoping for B. At large organizations, A is what the formal performance system pays out for (the promotion, the green OKR), and B is what would make the company win. Kerr’s argument is that the gap is structural and durable. Beating the startup often requires moves that hurt the next promotion packet: cannibalizing a sibling product, or shipping a risky bet that might miss the quarter. The reward system cannot be fixed from within, because the people who would fix it are the ones it selected for. The startup is the only party in the picture whose payoff requires winning the market.