Should i factor in vesting cliff and milestones in my equity offer?

[Kenneth_M]

I’m trying to figure out how to structure my first significant equity offer to a key engineer I’m bringing on board. I have a rough percentage in mind based on our current valuation, but I’m unsure how to factor in the four-year vesting schedule with a one-year cliff—does that sound standard, or should I be considering a different milestone-based approach?

[MasonD]

Yep, four years with a one year cliff is still the default for early hires. We did around 25% at year one and then vesting monthly for the remaining three years. It keeps people anchored to the project without locking them in forever.

[JackQP]

Milestone based can feel fair when you have crystal clear goals, but it often shifts incentives toward finishing a milestone instead of building steady value.

[DavidRH]

We tried tying chunks to product milestones like launch dates or feature completions, but we spent more time arguing about what counted than shipping.

[CamilaMW]

Question: is the issue really the vesting itself, or is the bigger problem the overall package, timing, or how you frame the offer?

[LoganCL]

I’ve wandered into admin land before and pulled comps, but the simplest path was the standard schedule, so I kept it.

[Jacob25]

Action I took: I ran a quick cap table/dilution rough cut to see how big a slice would feel, and it helped set expectations and a backup plan if retention dipped.

[Mia99]

And a final side thought about equity: it’s a long-term partnership, not a one-off number, so I’d test how it lands when you explain the long horizon and potential exits.