There's a folklore that 'startup equity isn't negotiable'. It is, especially for senior or in-demand roles. The trick is knowing what to ask for and how — equity has more dimensions than salary, and most candidates only push on one (number of shares).
Negotiable elements, in roughly decreasing order of how often candidates win
- Number of shares: most often negotiated. Typical successful asks are 15–40% above initial offer.
- Extended exercise window: ask for 5 or 10 years instead of the default 90 days post-departure. Costs the company nothing; saves you a fortune in optionality.
- Acceleration on change of control: 'double-trigger' (acquisition + involuntary termination) is standard senior hire ask. 'Single-trigger' (acquisition alone) is rare and hard to get.
- Early exercise option: lets you exercise unvested options and start the LTCG clock. Often available if you ask.
- Vesting schedule: 3 years instead of 4 is sometimes negotiable for senior hires. 6-month cliff instead of 12 is occasionally available.
How to ask
Frame it around competing offers and market data. 'I have another offer with X shares at a similar valuation; can you stretch?' is more effective than 'I want more equity'. Companies will counter or hold firm; either is information.
If you can only push on one thing, push on the extended exercise window. It costs the company nothing today, but it can save you $50K+ if you leave the company before the next liquidity event.