Common Mistakes When Hiring a Head of Sales

A Head of Sales appointment that underperforms is rarely a story about a bad candidate. It is far more often a story about a role that was never properly scoped, a process that selected for the wrong strengths, or expectations set at director level for a role pitched at management level.

These are the mistakes we see repeatedly in businesses making this appointment for the first time, or replacing one that did not work.

1. Leaving the scope undefined against other roles

Where a business already has, or plans to have, a Sales Director or Managing Director active in commercial decisions, an undefined Head of Sales brief creates overlap and confusion from day one. Both people end up making decisions the other assumed was theirs, and the new appointment spends the first quarter negotiating territory rather than managing a team.

Fix: write down explicitly what the Head of Sales owns, what they feed into, and what they have no part in, before the role goes to market — and share it with candidates during the process, not after an offer.

2. Hiring a strong seller instead of a proven manager

Interview processes are naturally drawn to people who sell well in the room. That is a reasonable instinct for a rep, and a poor proxy for this role. The evidence that actually predicts success is whether the candidate has built activity standards, coached underperformers into performers, and improved a team's collective output — not their own personal number.

• Ask what a specific underperforming rep's numbers looked like before and after they took over their coaching
• Ask how they define pipeline stages and what evidence each stage actually requires
• Ask what forecasting method they use and how accurate it has been historically
• Be cautious of an answer built entirely around the candidate's own deals rather than the team's

A brilliant personal closer with no coaching evidence is a strong argument for a senior sales role — just not this one.

3. Expecting strategic output from an execution-focused role

Businesses without a Sales Director sometimes hope a Head of Sales will also set commercial strategy, define pricing and choose which markets to prioritise. Most people who are genuinely strong at daily team management and coaching are not the same people who are strong at strategic commercial thinking — the two skill sets exist on a spectrum, and a role built at one end rarely delivers well at the other.

Fix: if strategic ownership is genuinely needed, either budget for a Sales Director or Commercial Director, or accept that the Head of Sales will need significant strategic direction from above rather than being expected to originate it.

4. Under-resourcing the first ninety days

5. Setting revenue expectations before assessing the inherited pipeline

A new Head of Sales inherits whatever pipeline and team habits already exist. Holding them to a revenue number set before anyone assessed that pipeline's real quality sets up an unfair and often unwinnable first year, and pushes toward the kind of optimistic forecasting that later damages credibility.

Fix: build in a short assessment window — often four to six weeks — before finalising the year's targets with the new appointment, rather than handing them a number set months earlier under different assumptions.

6. Choosing the wrong engagement model for the situation

Appointing permanently into a team that is still finding its shape, or engaging fractional cover for a team that genuinely needs daily coaching, both waste time. Match the model to the actual size and stability of the requirement, not to whichever felt like the default choice.

7. Running a slow or inconsistent process

Strong candidates for this role are usually currently employed and have options. A process that drags across several unstructured conversations, changes the brief midway, or goes quiet for weeks between stages loses good people before an offer is even made.