Updated November 2026
Answer the risk before you sell the vision. A senior candidate leaving a large company is quietly asking five questions: will this company exist in two years, what will I own, who will I work with, what is the upside and what happens to my career if it fails. Give checkable evidence for each, in that order, across your interview process, and keep the equity conversation until the first three are settled.
Most founders pitch a senior hire the way they pitched their seed investors, with the vision, the market and the demo. The candidate is doing different maths. They are pricing the risk of swapping a stable, well-paid job for yours, and every conversation either lowers that price or raises it.
We will follow one illustrative case: Marcus, founder of a nine-person seed-stage software company, hiring a VP Engineering from a large tech company.
Senior people rarely ask these out loud. They ask a softer version, such as "how is runway looking?", and judge how directly you answer.
Equity means little to someone who doubts the company will last. Founders who open with the option grant tend to get polite interest and no decision.
A senior candidate has heard every founder line before. What moves them is anything they can verify themselves.
| Question | What founders usually say | Evidence a sceptic can check |
|---|---|---|
| Will it exist? | "We are well funded." | Runway in months, the next funding milestone and permission to call your lead investor. |
| What will I own? | "You will have lots of autonomy." | A one-page scope naming the decisions they make alone and their hiring budget. |
| Who will I work with? | "The team is amazing." | Time with the team without you in the room. |
| What is the upside? | "Meaningful equity." | What the grant is worth at three exit values, from real share numbers. |
| What if it fails? | Usually nothing. | An honest answer and a reference from someone who joined early and has since moved on. |
Model the grant before the offer call with our stock option calculator. If cash is the sticking point, our guide on hiring without matching big tech salaries covers how to close the gap. Option terms and tax treatment differ by country, so have your lawyer review the offer paperwork.
This example is illustrative. Marcus was still the only person reviewing pull requests at midnight. The strongest candidates he met were engineering directors at large companies, with unvested stock and teams they liked.
His first finalist declined after a good process. Marcus changed the order of his process for the next finalist, without changing the offer much.
The second finalist asked for more equity, slightly less cash and the scope attached to his offer letter. Marcus agreed. The process took the same number of weeks, but every meeting answered a question the candidate already had.
Almost no candidate will ask "what happens to my career if you fail?", yet it often decides the offer, and their partner at home is usually asking it too. Raising it yourself is the most disarming thing a founder can do.
Be concrete about what they will have done by then. Growing a team from three to fifteen and reporting to a board is a story that gets someone a CTO role elsewhere, even if your company does not make it.
Then offer a reference from someone who joined early and has since left. They carry more weight than any current team member, because they have nothing to gain.
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Usually not, provided the gap is explained and the equity is shown in real numbers. Ask early what they need to cover their fixed costs, and design the offer around that figure.
Share runway and the next funding milestone on the first call. Share the fully diluted share count and option terms at offer stage, once both sides are serious.
Yes, offer it before they ask. A short call with your lead investor lets the candidate test your story with someone independent. Brief the investor on the candidate's likely concerns beforehand.
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