The first hire after $1M ARR
Founders who get to $1M with three people often make their worst hire as the fourth. The trap is hiring for the company they imagine, not the one they have.
Crossing $1M ARR with a tiny team feels like vindication. Then comes the urge to hire a Real Head of Something — sales, marketing, engineering. The new hire arrives with a playbook from a much larger company, runs the playbook, and breaks the thing that worked.
Why it fails
At $1M, the company is still product-led, scrappy, and reliant on the founders' intuition. A senior executive expects systems, headcount, and budget — none of which exist yet. They spend their first quarter trying to build the missing infrastructure instead of doing the work.
Hire one level down
What you usually need is a great senior individual contributor who can ship, not a director who needs a team. The director version can come a year later, once there's something for them to direct.
Hire for the company you have, not the one you're imagining you'll be in twelve months.