Preparing for Your First Head of Sales – Andre DeRussy

The threshold most operators use is $1.5M–$3M ARR with at least one non-founder rep closing deals repeatably. Below that, a VP Sales typically has nothing to manage and ends up doing individual contributor work they were not hired – or priced – to do. Above $3M ARR with multiple reps and a working motion, you are likely already late. The right moment is when you have enough evidence of repeatability that a VP Sales can document what exists and build on it – not invent it from nothing.

The highest-signal questions are about documentation and self-sufficiency. Ask: "Walk me through the last sales playbook you built from scratch – what triggered it, what you put in it, and how you validated it worked." Ask: "Describe a time you inherited a broken motion – what was the first thing you fixed and how?" Ask: "What would you need to see in the first 30 days to know whether this role is the right fit?" Candidates who have only scaled existing motions will struggle to answer the first two questions with specifics. Candidates who have built from scratch will answer immediately.

Three practices reduce early failure significantly. First, build the infrastructure before the hire – playbook, CRM, at least one rep – so the VP Sales inherits a working system. Second, define the success criteria for the first 90 and 180 days before making the offer, and share them with the candidate before they sign. Third, keep the founder in at least one deal per week for the first 90 days so there is continuity between founder-led relationships and the new motion. Most VP Sales failures trace back to one of these three gaps.

Not immediately, and not completely. The transition works best when the founder moves from primary closer to strategic support over 90–120 days – staying in select enterprise deals, handling C-suite relationships, and attending key board presentations, while the VP Sales owns the pipeline, the reps, and the operational motion. A clean break on day one almost always creates problems: customers ask for the founder, the VP Sales inherits deals mid-cycle without context, and the founder second-guesses from a distance. Staged transition with a clear milestone – "founder exits day-to-day sales when the VP Sales closes their first unassisted enterprise deal" – works better.

For a Series A B2B company at $2M–$5M ARR, a VP Sales with five to eight years of relevant experience typically expects $180,000–$240,000 base, $360,000–$480,000 OTE at plan, and 0.4%–0.8% equity vesting over four years. Early-stage VP Sales candidates with the specific profile – built a motion from scratch, managed a team under ten reps, comfortable in unstructured environments – sometimes accept lower base in exchange for higher equity. Candidates from large enterprise backgrounds (Salesforce, Oracle, SAP) typically expect higher base and are often wrong-fit for early stage, regardless of comp structure.