The First 10 Hires: Who I Actually Want in the Room

The First 10 Hires: Who I Actually Want in the Room

Most early teams hire like a mini‑corporate org chart. I care less about titles and more about what the first 10 humans can actually own and fix.

1. The wrong way: mini‑corporate mode

The default pattern:

• CEO

• Head of Marketing

• Head of Sales

• Head of Product

• Head of Everything Else

It looks impressive on LinkedIn. It’s terrible in a 5–10 person company.

Why? Because:

• Everyone wants to “own strategy”

• Nobody actually does the work

• Coordination overhead explodes

Titles are cheap. Execution is not.

2. The roles I actually want early

In no particular order, my ideal early roster:

• 1 founder‑seller (sometimes me)

• 1 full‑stack product builder (code + UX instincts)

• 1 ops / RevOps brain (loves systems, hates chaos)

• 1 customer success / support hybrid (lives in the inbox)

• 1 marketer / storyteller (good at copy, not just performance dashboards)

• 1 data / analytics‑minded person (even part‑time)

• The rest: “athletes”—people who can flex across roles

I don’t care what you call them. I care whether they move revenue, product, or both.

3. My hiring bar for the first 10

For the first 10, my bar is:

• Owner mindset: they say “I’ll figure it out,” not “That’s not my job.”

• Communication: can explain what they’re doing, why, and what they need.

• Taste: they know what “good” looks like in their craft.

• Speed: they can ship a v1 without being hand‑held.

Red flags:

• “In my last big company, we had a process for this…” (and they want to copy‑paste it)

• Need very tight scope to operate

• Want to manage before they’ve done

4. Comp and equity: my simple philosophy

I won’t drop numbers here because markets differ, but the principles:

• First 10 get meaningfully more equity than later hires.

• I’d rather slightly overpay than negotiate them into resentment.

• I make the link between value created and upside extremely clear.

If someone doesn’t care at all about equity, I at least ask why. Not a hard no, but a yellow flag.

5. Onboarding the first 10 like co‑founders

My onboarding is very simple:

• Day 1–7: absorb context (customers, product, numbers)

• Day 8–30: ship real work that goes live

• After 30 days: own a clear metric and a roadmap

If someone is still in “learning mode” after 60 days in a 10‑person team, something is wrong—with them, with me, or with the role.

6. A quick template for your next hire

Before you hire #5, #7, or #10, write this down:

• This person’s superpower is: ______

• The one metric they will move is: ______

• In 90 days, success looks like: ______

• If they disappeared tomorrow, we would feel it because: ______

If you can’t answer those, you’re not hiring—you’re collecting people.