What we keep when we're underway. Field notes from running sales searches for founder-led companies pushing into bigger water. Long enough to be useful. Short enough to be read.
The sales team that got you to $20M is rarely the team that takes you to $50M. The motions change, the comp plans change, and the leaders you need are often not the ones in seat. A field guide to the second leap.
When a search fails, the founder usually blames the firm. Sometimes that's right. More often, the role itself was scoped wrong — built for a stage the company hasn't reached, or for a motion the company has already outgrown.
Founders spend three months on the search. Then they spend the next three months unable to let go of their biggest accounts. The hire doesn't fail because the leader is wrong. It fails because the handoff never happened.
The first BDR hire is rarely the hire that defines the function. Notes from building the outbound motion at a $4M ARR company — the org design, the comp model, the playbook, and the mistakes we made along the way.
The most common mistake we see in late Series A and early Series B: founders hire the team they need today, then have to re-hire half of it eighteen months later. The right scope is one stage ahead — and the firm that can hire there.
A working note on what first-CRO comp actually looks like for founder-led companies between $5M and $30M ARR. Base, OTE, equity, accelerators, and the most common mistakes founders make in offer architecture.
The most common scoping error in our work. Founders pattern-match to the title their peers are hiring. The right scope is almost always one rung lower — and the hire holds.
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