Fundraising6

The Option Pool Mistake That Almost Cost Us Our First VP of Engineering

We had a signed offer letter and 0.6% left in the pool for a 1.5% ask. Here's how a VP Engineering hire nearly fell apart over sizing math.

We had the offer letter drafted, the VP of Engineering candidate had verbally accepted, and I was already picturing our first real engineering leader showing up on day one. Then our cap table software flagged something I hadn't checked in three months: 0.6 percent left in the option pool, against an offer that needed 1.5 percent to be competitive.

The math didn't work, and the candidate had another offer with a start date two weeks out. That's a bad place to discover you've mismanaged the most important recruiting lever a pre-revenue startup has.

Here's what happened, and the numbers that would have caught it four months earlier.

Where the pool actually went

We'd sized our option pool at 12 percent going into seed, which sits comfortably inside the 12 to 15 percent range Carta's benchmark data shows is typical at that stage. On paper, that looked like plenty of room to hire six or seven people before our next round.

What the sizing exercise didn't model was the shape of who we'd actually hire. Our first four hires were individual contributors, at 0.15 to 0.3 percent each. Cheap, in pool terms.

Hire five was the VP of Engineering search. VP-level grants at seed stage run 1.0 to 2.5 percent, per Index Ventures' benchmarking data, five to ten times the size of the ICs we'd already granted. We'd tracked shares granted against pool size and watched the top-line number stay comfortable. We hadn't modeled that one senior hire could eat what four ICs had left untouched.

The number that actually mattered

By the time we opened the VP Engineering search, granted shares against the pool showed 68 percent used, which still read as fine on the dashboard. What that number didn't show: two pending refresh grants for early employees approaching their one-year cliff, already board-approved but not yet issued. Add those in and available shares dropped to 0.6 percent, not the 32 percent the dashboard implied.

Available equity for a new senior hire is pool size minus granted minus committed, and committed is the number that lives in board minutes and Slack threads, not in most cap table tools by default. We were reading the wrong number for four months and didn't know it.

How we actually fixed it

With a signed verbal offer on the table and two weeks before the candidate's other deadline, we didn't have time for a leisurely board process.

We went back to our lead investor the same week with the real numbers: current pool, committed grants, and the specific gap for this hire. Because we came with a clean breakdown instead of a vague warning that we were running low, the board approved a 3 percent pool top-up by written consent in four days instead of waiting for the next scheduled meeting.

We also restructured the offer slightly: 1.1 percent at grant, with the remaining 0.4 percent as a documented follow-on grant tied to a six-month milestone, pre-approved as part of the same board resolution. That kept the immediate ask inside what was actually available while still landing at the full number the candidate expected.

The hire closed. But a same-week emergency board resolution is not a repeatable process, and I don't recommend building a hiring plan around getting lucky with a responsive investor.

What I'd track differently now

The fix that actually stuck wasn't the emergency top-up, it was changing what number we look at monthly. We now review three figures alongside cash runway: shares granted, shares committed (offers out, board-approved refreshes not yet issued), and what's actually available once both are subtracted from pool size.

We also stopped sizing pool math around headcount alone. A pool built for seven hires without accounting for seniority mix will run out early the moment one of those seven is a VP-level role instead of another IC, because the multiple is 5 to 10x, not a rounding error.

The takeaway

If you're heading into a senior hire and haven't checked committed grants against available pool in the last month, do that before you extend an offer, not after a candidate has already verbally accepted. A VP-level grant at seed or Series A routinely runs 1.0 to 2.5 percent of fully diluted equity, five to ten times a typical IC grant, and a pool that looks 30 percent available on a dashboard can be effectively empty once pending commitments are counted. Check available, not granted, before you write the offer number down.

Frequently asked questions

How much equity does a VP of Engineering typically get at a startup?

At seed stage, VP-level hires typically receive 1.0 to 2.5 percent of fully diluted equity. At Series A, that range compresses to roughly 0.5 to 1.5 percent, with product and engineering roles at the higher end.

What's the difference between granted and available option pool shares?

Granted is shares already issued against signed offers. Available is pool size minus granted minus committed, where committed includes board-approved refresh grants and pending offers not yet issued. Most cap table dashboards default to showing granted, which overstates what's actually free to offer a new hire.

Can a board approve an option pool top-up outside of a scheduled meeting?

Yes, an emergency top-up can be approved by written consent between meetings if the board agrees, but it requires a clean, specific ask rather than a vague low-pool warning, and it shouldn't be the default plan for time-sensitive senior hires.

Should I structure a senior hire's equity grant differently if the pool is tight?

A split grant, a smaller immediate grant plus a board-pre-approved follow-on tied to a milestone, can bridge a temporary pool gap without underpaying the candidate relative to the full offer.

If you haven't set up monthly tracking yet, the three-number run-rate check catches this months before an offer letter forces the timing.

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