You've tailored the cover letter. You've optimized for keywords. The startups you want still don't reply. The gap isn't your experience; it's that founders don't hire like corporate recruiters. They're not scanning for credentials. They're asking one thing: will this person be more work for me than the work they take away?
Early-stage founders aren't filling slots. They have a pain they want off their desk. When they sit across from you, they're weighing whether you'll run with that pain without hand-holding, whether you'll adapt as the role changes, and whether you can pay for yourself directly or by freeing them to sell or raise. Job descriptions are often placeholders. What they need is someone who can say what they'll take off the table and then do it.
That changes how you search. Job boards bury you. Getting in sideways does not: talk to someone who already works there, show up at startup events, volunteer in the ecosystem. When you're in the room, ask about the company and the vision. When they ask what you do, be specific about what you've built or run, then add that you'll take any project they need. The signal that gets offers is humility and willingness, not heroics. Founders hire people who will run with it, not people who need to be managed.
Compensation at startups usually means less base and more variable. Equity is a lottery ticket; treat it that way. Variable comp only makes sense when you can actually move the outcome. Proposing "I make money when I make you money" aligns you with the founder and makes it easier for them to say yes, but only if you can deliver. The real upside for the right person is learning: you see how a business is built and where it breaks, across functions, in a fraction of the time it takes in a big company. If that trade works for you, you're in the right room.
Watch the Full Episode on what founders actually want when hiring with Anthony, Chris, and Stephanie below:
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