How Senior Leaders Negotiate Equity Grants

Episode notes

In this episode, Lucas and Luna dive into the art of negotiating equity compensation at the senior leadership level. Using the example of a hypothetical VP of Product who received a 0.5% stake at a Series B company, they break down the key levers: vesting schedules, acceleration clauses, single vs. double trigger, and the often-overlooked difference between incentive stock options (ISOs) and non-qualified stock options (NSOs). Lucas explains why most executives should negotiate for a shorter cliff, single-trigger acceleration, and extended exercise windows post-departure. Luna pushes back on the standard 90-day exercise window and shares data showing that over 60% of startup employees let options expire worthless. The conversation also touches on how to value illiquid equity, the role of 409A valuations, and why talking about dilution early matters. A must-listen for any senior leader evaluating an offer with equity components.