There’s so much discussion on LinkedIn and social media about how folks especially VPs of Sales should negotiate hard on the way in.
Maybe. Go for it, by all means.
But I think these posts miss a key second post. There’s an even better time to negotiate hard in many cases — around Year 2, when you’ve totally crushed it:
- When you’ve now built up a great team
- When things have accelerated
- When you outperformed everyone’s expectations
This is so rare, especially these days. To hire a leader that truly crushes it and goes above and beyond.
If that’s you, then for sure, 365 days in:
- Ask for that promotion to CRO (or whatever)
- Ask for SVP-level equity, or at least, another grant
- Push for a higher OTE that ties — to the results you’ve delivered
90% of CEOs, they may not have gotten it right at first. But the last thing most founders want is a truly high-performing leader moving on after a year.
Do it the right way. Don’t make threats you’re going to leave. But also, don’t feel like you have to get everything on Day 0.
It’s worth a shot. But you get another chance to push for more when you’ve truly earned it.
A related post here:
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Jason Lemkin, Khareem Sudlow
