Lenny RachitskyHost of Lenny's Podcast | Author of Lenny's Newsletter

You should be losing most of your deals

27 Aug 2026 · 1 min

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In this segment, Lenny Rachitsky explains that a healthy win rate for enterprise sales is typically between 25% and 35%, contrary to the common expectation of a 50% win rate. He notes that win rates higher than this range often signal that pricing is too low, as many market segments lack the maturity to sustain higher prices. Additionally, he highlights that roughly 25% of deals that are initially lost tend to return (or "boomerang") about a year later, emphasizing that it is normal for a significant portion of deals not to progress immediately.

Chapters

The win rate for enterprise, a good healthy win rate, it's actually probably gonna surprise you. It's not 50%. A healthy win rate is usually around, I would say between 25 and 35%. If your win rate is higher than that, your price is too low. There's a lot of part of the market that's just not in a maturity perspective to take you on, and that's healthy. The amount of deals that come, that boomerang a year later of the ones that have lost, that's probably another 25%. So it is totally normal and natural for deals to not advance.