The Equity Conversation Most Founders Aren't Ready For

A senior engineer will ask you about equity. And most founders stumble through that conversation in a way that kills the offer — not because the equity is bad, but because the founder clearly hasn't thought about it carefully. That stumble doesn't just lose the candidate. It signals something about how you run the company.

Here's what unprepared looks like versus prepared. The unprepared founder quotes a percentage and moves on. But that percentage means nothing without knowing the post-next-round dilution, the current 409A valuation, the strike price, and how the vesting schedule handles acceleration. An engineer who's done this before will ask all four. If you can't answer them cleanly, you've signalled that your cap table is a mystery to you. The prepared founder has thought through each of these in advance, knows the answers, and can explain them without hedging.

Know these four things before that conversation happens. One: your current fully diluted share count and what it becomes after your next round. Two: the 409A valuation and what the strike price actually means in dollars at your current valuation. Three: the vesting schedule — four years, one-year cliff, and whether you offer acceleration on acquisition. Four: how many options the role gets, as a percentage of the fully diluted post-raise cap table — not the current one. An engineer who's been through an exit will ask exactly these four things. Be ready.