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Dear SaaStr: I’ve Started to Hate Selling. Would I Be Happier as Sales Manager Instead?

Dec 9, 2025

Dear SaaStr: I've Started to Hate Selling. Would I Be Happier as Sales Manager Instead? No. Not after a brief moment. Because you will fail at it. So you will also hate sales management. Maybe not being a founder, or a manager in another function. But you will...

Why Your Startup Will Fail, If It Does Fail: The Drama Inside, Not Outside

Dec 8, 2025

The brutal truth about what actually kills high-growth companies I've now been involved in 100+ B2B startups as an investor, advisor, or founder. I've watched companies go from $0 to $1000M ARR. I've seen unicorns born. And I've seen what looked like rocket ships...

Dear SaaStr: How Should I Actually Set the Sales Plan for the Year For My VP Sales?

Dec 8, 2025

Dear SaaStr: How Should I Actually Set the Sales Plan for the Year For My VP Sales? Try the C10, C60, and C90 framework. C = Confidence. https://twitter.com/jasonlk/status/1577403391164104704?s=61&t=ZWlHxY1IQMwjLHbJx9Z4OA You’re essentially building three layers...

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