Don't Hire a Head of Sales Yet
The hire feels like the fix. It's usually the cap. Until the founder has closed ten deals on the same playbook, the Head of Sales has nothing to inherit.
The Head of Sales feels like the unlock. The founder is exhausted from selling. The board is asking when the motion scales. The candidate has a real resume. The offer goes out.
Six months later the VP is still figuring out who the buyer is, the pipeline looks worse than when the founder was running it alone, and the board is asking what went wrong with the hire.
Nothing went wrong with the hire. The hire was made one year early.
The Head of Sales role exists to scale a motion that already works. The role does not exist to discover the motion. Discovery is the founder's job. A VP hired before the motion is written ends up writing it — out of their last company, which sold a different product to a different buyer at a different price point. The playbook they build is plausible. It is also not your playbook. You will spend the next six months either rewriting it after them or watching the team execute it into the floor.
The readiness signal is ten. Ten closed deals on roughly the same motion. Same ICP, same discovery flow, same demo, same procurement path, same close cycle. Written down well enough that a new rep could execute against the document on day one. If the founder cannot write that document — if every deal feels bespoke, every close required a different unlock — the motion is not yet a motion. It is a series of personal sales.
Personal sales do not transfer.
The math against early hiring is brutal. The fully-loaded cost of a Head of Sales is roughly four hundred thousand a year. The opportunity cost — the time the founder spends managing the hire instead of closing deals — is another quarter. The six-month ramp produces zero pipeline. By the time you know the hire was premature, you have spent two years of runway on the wrong sequence.
The cleaner sequence: founder closes ten on the same motion, writes the playbook, hires an Account Executive to run the playbook for three more closes, then hires the Head of Sales to scale what is now demonstrably scalable. The VP arrives to a working motion and grades up the execution. The hire works.
Most boards push for the VP early because the VP is a visible artifact. We hired a Head of Sales is easier to put in an update than the founder closed three more this quarter while writing the discovery script. Resist the push. The visible artifact and the right move are different things.
The founder you replace yourself with should be replacing a function the founder no longer needs to do. Until the motion repeats, the founder is the function.