7 Steps to Hire Your First Head of Sales

Hiring your first Head of Sales is one of the most important commercial decisions a growing business will make.

The right person can turn founder-led selling into a repeatable sales operation, recruit and develop a high-performing team, improve forecasting and create a predictable route to revenue growth.

The wrong person can introduce unnecessary processes, hire the wrong salespeople, miss targets and consume months of salary, commission and management time before the business recognises the mistake.

This is also a uniquely difficult appointment. You are not hiring someone to inherit a mature sales department with established processes, reliable data and clearly defined territories. Your first Head of Sales may need to create many of those things from the ground up.

Here are seven steps to finding the right person.

1. Confirm That You Are Ready for a Head of Sales

Before beginning the search, determine whether a Head of Sales is genuinely the appointment your business needs.

Some companies hire too early. They expect one person to validate the product, define the market, generate every opportunity, close every deal, recruit a team and create the entire commercial strategy.

That may be closer to a founding salesperson or senior business-development hire than a conventional Head of Sales position.

Other businesses hire too late. The founder remains involved in every opportunity, individual salespeople work in different ways and forecasting depends more on optimism than evidence.

You may be ready for your first Head of Sales when:

• The business has evidence of product-market fit.
• There is a defined or emerging ideal customer profile.
• The founder or existing team has already closed repeatable business.
• There is enough market opportunity to justify building a sales function.
• Several salespeople need consistent direction and accountability.
• The business needs more reliable pipeline management and forecasting.
• The founder needs to transfer day-to-day sales leadership to someone else.

A Head of Sales cannot repair every weakness in the business. If the offer is unclear, customer retention is poor or the company has not identified a viable market, changing the sales leader may not solve the underlying problem.

2. Define the Commercial Outcome, Not Just the Responsibilities

Many Head of Sales job descriptions contain familiar responsibilities:

• Develop the sales strategy.
• Manage and motivate the team.
• Build relationships with key customers.
• Deliver revenue growth.
• Report sales performance to the board.

These points describe the function, but they do not define what the person must accomplish.

Create a measurable success profile before starting the search. It should explain what success looks like after 90 days, six months and the first year.

Depending on the stage of the business, this could include:

• Assessing the existing team, pipeline and sales process.
• Defining market segments and ideal customer profiles.
• Introducing qualification standards and opportunity stages.
• Establishing credible pipeline coverage and forecasting.
• Recruiting and onboarding additional salespeople.
• Improving conversion rates or shortening the sales cycle.
• Winning a defined number of strategic customers.
• Delivering a specific new-business revenue target.
• Reducing the founder’s involvement in routine sales management.

Agree on the numbers internally. If the founder, board and finance team have different expectations, even a strong candidate can appear unsuccessful.

The scorecard used to select the candidate should later become the foundation of their performance plan.

3. Decide Whether You Need a Builder, a Scaler or a Turnaround Leader

Not every successful Head of Sales is suited to every commercial environment.

A leader who managed 50 salespeople in a recognised international company may struggle in a business where there is no sales operations support, limited marketing resource and an incomplete CRM.

Equally, an entrepreneurial sales leader who thrives on building everything personally may not be the best choice for a company that now needs structure, delegation and operational discipline.

There are three broad profiles to consider.

The builder

A builder is comfortable creating the foundations: messaging, territories, sales stages, reporting, recruitment and early customer acquisition. They are usually willing to remain personally involved in important deals.

The scaler

A scaler takes something that already works and makes it larger, more consistent and more predictable. They are often strongest in team development, process improvement, forecasting and multi-market growth.

The turnaround leader

A turnaround leader diagnoses why an established team is underperforming and makes difficult changes. They may need to restructure territories, replace people, improve accountability and rebuild confidence.

Be honest about the environment the candidate will inherit. A title alone does not demonstrate suitability. The relevant question is whether the person has succeeded under comparable conditions.

4. Set a Realistic Package and Incentive Plan

Determine your budget using current market evidence, the complexity of the appointment and the results expected from the individual.

The package will normally include:

• Base salary.
• Target-based bonus or commission.
• Benefits.
• Equity or share options, where appropriate.
• Clear rules governing when variable compensation is earned.

Do not advertise an impressive on-target earnings figure unless the target is genuinely achievable.

Candidates will want to understand:

• How the target was calculated.
• Whether anyone has previously achieved comparable results.
• The value and quality of the current pipeline.
• The average sales cycle and contract value.
• Available marketing and lead-generation support.
• The size and capability of the existing team.
• Their authority to recruit or restructure.
• How much of their target depends on personal selling.

The best sales leaders examine the commercial assumptions behind the package. Detailed questions about pipeline, conversion rates and resources are normally signs of commercial discipline, not reluctance.

A package below the relevant market rate often creates a false economy. The financial consequences of a failed sales-leadership appointment can be substantially greater than the salary difference required to attract the right person.

5. Search Beyond Active Applicants

A job advertisement may attract capable candidates, but the strongest person is not always actively looking for a new position.

Successful sales leaders are often delivering results, earning commission and treated well by their current employers. They may listen to a compelling opportunity, but they are unlikely to discover it through a generic advertisement.

Build a target market around evidence that matters:

• Businesses with similar products, customers or sales cycles.
• Leaders who have operated at a comparable growth stage.
• Candidates who have built teams, not merely inherited them.
• People who have entered new markets or launched new propositions.
• Leaders who have sold at the required deal size and seniority.
• Candidates with experience of the company’s target geography.

Direct experience with a competitor can be useful, but it should not become the only criterion. A candidate from an adjacent sector may bring stronger leadership, a more relevant sales motion or experience solving the exact growth problem your business faces.

For a revenue-critical appointment, a specialist sales headhunter can also reach passive candidates, test the market and provide an informed comparison between applicants and individuals who would not otherwise enter the process.

6. Interview for Evidence, Not Presentation Skills

Sales leaders are usually accomplished communicators. A confident interview, however, is not proof that someone can build and lead your sales operation.

Use structured interviews based on the scorecard created at the beginning of the search. Ask every serious candidate comparable questions and assess the quality of the evidence behind their answers.

Useful questions include:

• What commercial situation did you inherit in your last role?
• What was the revenue target, and what result did you deliver?
• How much of that growth came from existing accounts versus new business?
• What did the pipeline look like when you arrived?
• What changes did you make during your first 90 days?
• How did you determine which salespeople could succeed?
• Tell us about a sales hire that did not work. What did you learn?
• How did you improve forecast accuracy?
• Which conversion metrics did you monitor?
• Describe a target you missed and why.
• How involved were you personally in winning strategic opportunities?
• What resources were available to you?

Look for specific numbers, starting conditions, actions and results. Clarify whether the candidate personally led the work or was part of a larger organisation that produced the outcome.

A practical assessment can provide additional evidence. Give the candidate realistic information about your market, people, pipeline and objectives, then ask them to present:

• Their initial diagnosis.
• Priorities for the first 90 days.
• The information they would need before making changes.
• The risks they see.
• The metrics they would introduce.
• How they would balance immediate revenue with long-term development.

Do not expect a complete unpaid sales strategy. The purpose is to assess how the candidate thinks, prioritises and challenges assumptions.

Include the founder and relevant stakeholders, but avoid an excessive interview process. Strong candidates are likely to be considering other opportunities, and unnecessary delays can result in losing them.

7. Complete Due Diligence and Build the First 90-Day Plan

Reference checking should test the claims that influenced your decision.

Whenever possible, speak directly with former managers, peers and team members. Ask about:

• The commercial situation the candidate inherited.
• The targets for which they were accountable.
• The results they personally delivered.
• Their approach to forecasting and pipeline management.
• The quality of the people they recruited.
• How they handled underperformance.
• Their leadership and communication style.
• Whether the referee would hire them again.

Listen carefully for vague or qualified answers. Important information is often contained in what a referee hesitates to confirm.

Once you have selected the candidate, move decisively. Present a clear written offer covering salary, variable compensation, benefits, reporting lines, authority and performance expectations.

The recruitment process does not end when the offer is accepted. Before the person starts, agree on a structured onboarding and 90-day plan.

During the first 30 days

The new Head of Sales should learn the business, meet key customers and stakeholders, assess the team, review the pipeline and understand the available sales data.

During days 31–60

They should begin defining priorities, correcting obvious weaknesses, establishing reporting standards and agreeing on the sales strategy with leadership.

During days 61–90

They should start implementing the agreed plan, coaching the team, addressing capability gaps and producing a more credible view of future revenue.

Avoid demanding immediate wholesale changes before the new leader understands the business. At the same time, do not leave authority ambiguous. If the Head of Sales is accountable for the number, they must have appropriate influence over the people, process and resources required to deliver it.

Common Mistakes When Hiring a First Head of Sales

Several mistakes repeatedly lead to unsuccessful appointments:

• Hiring a famous company name rather than examining the candidate’s individual contribution.
• Choosing the best salesperson instead of the best sales leader.
• Expecting one person to solve product, marketing, positioning and sales simultaneously.
• Hiring a corporate scaler into an early-stage builder role.
• Using an unrealistic OTE to compensate for a weak base salary.
• Failing to agree internally on targets and priorities.
• Accepting general claims without verifying numbers.
• Running a slow, inconsistent interview process.
• Providing responsibility without sufficient authority or resources.
• Judging the appointment only on immediate revenue before accounting for the sales cycle.

Final Thoughts

Your first Head of Sales should not simply be the most senior or impressive candidate available.

They need to be the right sales leader for your company’s current stage, target market, commercial model and growth objective.

Define the outcome before defining the person. Search for evidence from comparable situations. Test that evidence carefully. Then give the successful candidate the authority, information and support needed to deliver.

The Sales Experts recruits proven sales leaders, including Heads of Sales, Sales Directors, Commercial Directors and VPs of Sales, across the UK and international markets.

If your next sales-leadership appointment is critical to revenue growth, contact us to discuss how we can identify, assess and secure the right person for your business.