Maya messaged me on a Tuesday afternoon: "can we talk this week?" I'd been running the company for four years by then, long enough to know exactly what that sentence meant before I even opened the calendar invite she sent back.
She was our fourth engineering hire, joined at seed stage on a standard four-year option grant, and was six weeks from being fully vested. Her manager hadn't flagged anything. Performance reviews were strong. I genuinely had not thought about her equity position in close to two years, because once the offer letter is signed, equity has a way of disappearing from how a founder thinks about compensation. It just sits there, quietly finishing its vest, until it finishes.
The conversation I almost got wrong
She wasn't unhappy with the work. She had a competing offer: about 15 percent more base salary, plus a fresh four-year grant at a company two years earlier in its life than ours. On paper our company was worth more. To her, the new grant felt like more, not less, because it represented four full years of upside instead of six weeks of nothing left to vest.
My first instinct was to counter with a cash bump. That would have missed the actual problem. The issue was never her salary. The issue was that her unvested equity, the thing that was supposed to make leaving expensive, had quietly shrunk to almost nothing, and I had let it happen without noticing.
What I'd gotten wrong for two years
I had budgeted equity like a one-time hiring cost instead of an ongoing retention lever. Maya had been promoted twice since joining, first to senior engineer, then into a de facto tech lead role on our core product. Both promotions came with title changes and modest cash increases. Neither came with additional equity, because nothing in our process ever asked the question. We had a hiring checklist. We didn't have a refresh checklist.
Industry compensation data backs up why that gap matters more than founders assume: employees whose original grant is between 40 and 60 percent vested show the highest measurable flight risk, higher than employees at 20 percent or at 90 percent. It's the window where the remaining unvested shares stop feeling large enough to outweigh a competing offer, but the employee still has enough runway left that a good outcome is genuinely still possible if you act. I sailed past that window with Maya by roughly eight months.
The refresh I should have made eight months earlier
Her original grant was a little under half a percent of the company at hire. By the two-year mark, roughly half of it had vested, which is precisely the point the data says a refresh should already be on the table. Her first promotion happened right around then. That promotion was the trigger I missed, not a calendar reminder, not a review cycle, an actual change in scope that should have come with a second grant.
What we actually did, eight months late
We put together a refresh grant sized at roughly 35 percent of what a new hire at her current, senior level would receive today, vesting on its own four-year schedule starting immediately. I did not frame it as a counteroffer. I told her directly that the two promotions should have come with equity conversations we never had, that this was catching up on that, and that going forward it wouldn't take a resignation notice to trigger the next one.
She stayed. Not because the number matched her competing offer dollar for dollar, it didn't come close, but because the conversation itself changed what she was evaluating. She wasn't choosing between two piles of cash anymore. She was choosing between a company that had just shown her it tracks this and one she hadn't worked at yet.
The 20-minute habit that replaced my blind spot
Once a quarter now, I pull a list of every employee past their 18-month mark and calculate what percentage of their original grant is vested. Anyone who crosses 40 percent gets cross-referenced against their last promotion or title change date. If those two things line up, a refresh goes on the agenda for the next leadership meeting, before anyone has a reason to send me a "can we talk this week" message. It takes about 20 minutes a quarter. Maya's near-departure cost us weeks of anxious back-and-forth and a counteroffer negotiated from the weakest possible position, which is exactly what that 20 minutes is designed to prevent.
If you're a founder and you can't answer, right now, which of your first five hires crossed 50 percent vested in the last quarter, you have the same blind spot I had. Pull that list this week. It's a lot cheaper to check it on your own timeline than to find out on theirs.