Hiring a sales leader is one of those decisions that can look straightforward on paper and become complicated once the person joins. A candidate may have an impressive revenue record, experience at a recognised company and the confidence to handle a room full of executives. Yet none of these guarantees that the person will be able to build a successful sales team in a different business.
The difficulty lies in understanding what produced the candidate’s earlier success. Did they build the sales process themselves, inherit an established team or benefit from a strong brand and a steady flow of leads? Can they repeat those results with fewer resources, a different customer base and a team that needs direction?
Companies that want to hire a sales leader need to look beyond the final numbers and understand the decisions, relationships and working habits behind them.
Research published in the Journal of Personal Selling & Sales Management in 2024 highlights the challenge. In a survey of 182 sales leaders, 70.3% rated finding qualified sales candidates as a significant challenge. The same study found that 37.4% of managers reported that new salespeople took six months or longer to reach full productivity.
The findings concern sales talent more broadly, rather than executive appointments alone, but they point to an important lesson: recruitment does not end when a candidate accepts the offer. The real test is whether the person can contribute, develop others and deliver results in the environment they have joined.
When Should a Company Hire a Sales Leader?
The first question is not who to hire. It is what the business needs its next sales leader to do.
In an early-stage company, the founder may still be closing deals, meeting customers and figuring out which sales approach works. Hiring a senior executive too early can create another layer of management before the business has a repeatable process.
At a later stage, the problem may be quite different. The company has customers and a growing team, but forecasts are unreliable, salespeople follow inconsistent methods and the founder remains involved in every major deal. That is when a dedicated leader can bring structure and accountability.
Before starting the search, consider which situation best describes the business:
- Building from scratch: The company needs someone who can win early customers, establish a sales process and recruit the first team members.
- Scaling an existing operation: The priority is to improve conversion rates, develop managers, strengthen forecasting and make growth more predictable.
- Fixing declining performance: The business needs someone who can identify why deals are being lost, examine the pipeline and address weaknesses without immediately blaming the team.
- Entering a new market: The leader must understand unfamiliar customers, longer sales cycles, local competition or a different route to market.
These responsibilities call for different experiences. A leader who has spent years managing a large enterprise team may not be the best choice for a young company that needs someone willing to make calls, visit customers and build the process personally.
The right time to hire a sales leader is when the business can identify the problem that person is expected to solve and provide the authority and resources to address it.
A Strong Revenue Record Does Not Tell the Whole Story
Revenue figures are important, but they need context.
Imagine two candidates interviewing for the same position. The first grew annual sales substantially at a well-established company with a strong brand, experienced salespeople and a large marketing budget. The second achieved more modest growth at a smaller business, where they had to develop the pipeline, recruit employees and improve the sales process.
The first candidate’s results are impressive. The second candidate’s experience may be more relevant to a business trying to build its sales function. Neither should be selected on these facts alone.
A useful interview explores how the results were achieved.
Ask candidates:
- What were your targets, and how did performance compare with them?
- How much of your growth came from new customers, existing accounts or market conditions?
- What did you personally change in the sales process?
- How did you handle a period when the team missed its targets?
- Which employees did you develop into stronger performers or future managers?
- What would your former team say was difficult about working with you?
The final question is particularly revealing. Leadership is experienced by the people who work under it, not just by the executives who see the quarterly results.
A candidate who can explain a failed initiative, acknowledge a poor decision and describe what changed afterwards may offer more useful evidence than someone who presents every career decision as a success.
This is where executive recruitment becomes a matter of judgement rather than résumé screening. The objective is to understand how a candidate thinks, learns and leads when the numbers are not going in the right direction.
Case Study: What Salesforce’s Research Reveals About Sales Productivity
Salesforce’s State of Sales research offers a useful example of why a sales leader’s job extends beyond setting targets.
Salesforce, in a report released in 2024, revealed in its sixth edition that sales representatives devoted approximately 30% of their working hours to selling, while 70% were spent on non-selling activities. Among others, these activities included internal meetings, preparation and administrative work.
The finding are important because it changes the questions a company should ask when sales performance falls short.
A manager might initially conclude that the team needs more pressure, more calls or a higher activity target. But if employees spend most of their time on administrative work, increasing their targets without addressing the underlying problem may accomplish little.
A capable sales leader would investigate where time is going, which processes create unnecessary work and whether the team has the tools and information it needs to sell effectively.
The research is not a case study of one company hiring a new sales executive, nor does it prove that administrative work explains every missed target. It does, however, illustrate a practical leadership challenge: sales performance can be constrained by the system in which people work, not simply by individual effort.
When assessing candidates, ask them to describe a time they improved productivity without simply demanding more from their team. Their answer can reveal whether they know how to diagnose an operating problem before prescribing a solution.
What are the Leadership Qualities Which Matter After the Appointment?
A sales leader needs commercial ability, but the role also demands patience, communication and the capacity to bring people along.
Five qualities deserve particular attention.
1. The ability to coach
A leader should be able to explain how they helped an underperforming employee improve. Look for examples of specific feedback, practical training and measurable progress rather than broad statements about motivating people.
2. Sound judgement
Sales leaders are responsible for determining what opportunities deserve their scrutiny, for knowing when to negotiate and when to turn their back on a deal. Interview the candidates, whereby they will be asked to explain a particularly hard commercial decision they had to make.
3. Honest forecasting
An accurate forecast is useful even when the news is uncomfortable. A leader who identifies risks early gives the business time to respond. Someone who consistently presents optimistic numbers without evidence can leave the organisation unprepared.
4. The ability to work across departments
Sales depends on product quality, marketing, pricing, customer support and delivery. A leader who builds productive relationships across these functions is better placed to resolve problems that no sales team can fix alone.
5. Accountability
Ask what happened when a strategy failed. Did the candidate examine their own assumptions, communicate the problem and adjust the approach? Or did responsibility always sit with the market, the product or the employees?
These questions help distinguish someone who can personally close deals from someone who can create the conditions for a team to perform consistently.
Why Trust Matters in Executive Hiring
Senior appointments often begin through professional relationships. A founder may receive a recommendation from a trusted adviser, reconnect with a former colleague or meet a candidate through an industry network.
These introductions can be valuable, but familiarity should never become a substitute for due diligence.
A trusted referral tells the company where to begin looking. It does not establish whether the candidate can lead the existing team, handle the company’s challenges or work effectively with the founder.
A sound recruitment process should include clear expectations, structured interviews, relevant references and an honest discussion about the role’s difficulties.
This is especially important in founder-led businesses. Founders may have built the company through personal relationships and quick decisions, but a senior appointment affects more than their own working relationship with the candidate. It affects employees, customers and the organisation’s future direction.
Before making an offer, the founder and candidate should discuss questions that are sometimes left until after joining:
- How much authority will the sales leader have over hiring, budgets and sales strategy?
- Which decisions will remain with the founder?
- What resources are available to achieve the agreed targets?
- What is already working, and what needs to change?
- How will the company assess progress during the first six months?
Trust becomes meaningful when both sides understand the expectations and can discuss disagreements openly.
How to Hire a VP of Sales Without Relying on Instinct Alone
When considering how to hire a VP of Sales, it helps to establish a consistent process before meeting candidates. Otherwise, interviews can become a series of enjoyable conversations in which the most confident person makes the strongest impression.
A practical process has four stages.
- First, define the outcomes. Identify three to five priorities for the first year. These might include building a team, improving forecast accuracy, increasing conversion rates or entering a new market.
- Second, ask comparable questions. Every shortlisted candidate should be assessed against the same core requirements. Interviewers can then compare evidence rather than relying on general impressions.
- Third, introduce a realistic exercise. Share an anonymised sales pipeline or a business scenario and ask the candidate to identify the biggest problems, explain their priorities and outline what they would investigate before making changes.
- Fourth, check references carefully. Speak with former managers and, where appropriate, people who reported to the candidate. Ask about communication, coaching, decision-making and how the person responded under pressure.
A practical exercise is particularly useful when it reveals the candidate’s reasoning. The goal is not to reward the most polished presentation. It is to understand how the person approaches a problem they have not already solved.
The First 90 Days Matter More Than a Dramatic Promise
A new sales leader may arrive with a clear view of what should change. However, making sweeping decisions before understanding the business can damage relationships and remove processes that were working for good reasons.
A sensible first 90 days should balance listening with action.
- Days 1–30: Meet the team, review the pipeline, understand the customers and examine the existing sales process.
- Days 31–60: Identify the biggest constraints, validate the findings and agree on a small number of priorities.
- Days 61–90: Begin targeted improvements, establish operating routines and review early evidence of progress.
The priorities will depend on the business. A company with weak lead qualification may need a different plan from one with a long enterprise sales cycle or high customer churn.
Nor should every appointment be judged on whether revenue rises immediately. Some changes take longer to affect results. Early evaluation should also consider the quality of the diagnosis, the credibility of the plan, the team’s response and progress against agreed milestones.
This gives the company and the new leader a shared basis for reviewing performance instead of relying on shifting expectations.
Author’s Note:
From my perspective as a coach, observing people and their behaviour has reinforced the importance of looking beyond confidence and outward achievement when assessing leadership.
People can make a convincing impression in a meeting. What tells us more is how they respond when something goes wrong, whether they can listen without becoming defensive and how they treat people who have less authority than they do.
I believe these qualities deserve more attention during executive hiring. A sales leader may be responsible for revenue, but the way that person handles pressure influences the people expected to deliver it. If mistakes are met with blame, employees may become reluctant to raise problems. If expectations are clear and feedback is constructive, a team has a better chance of identifying weaknesses and learning from them.
This does not mean that kindness can replace commercial competence or accountability. A sales leader must still make difficult decisions, address poor performance and deliver results. The distinction lies in how those responsibilities are handled.
My view is that businesses should look for evidence of both ability and character. Ask candidates to explain their difficult decisions, listen to how they speak about former colleagues and examine whether their examples show a willingness to take responsibility. These details cannot tell an employer everything about a person, but they can make the hiring decision more considered.
The right appointment should give a business confidence in the numbers and in the way those numbers are achieved.
Frequently Asked Questions
What should companies look for when they hire a sales leader?
Companies should assess relevant commercial experience, team development, forecasting, strategic judgement and the ability to work across departments. Previous results should be examined in the context of the candidate’s responsibilities and available resources.
How do you know when a company needs a VP of Sales?
A company may need a VP of Sales when its sales operation has outgrown founder-led management, when it needs to build a repeatable sales process or when a more experienced executive is required to scale or transform the team.
Should companies hire a sales leader from the same industry?
Industry experience can help when the role depends on specialist knowledge, established relationships or complex buying processes. However, a candidate from another industry may also be suitable if their experience transfers to the company’s sales model and customer needs.
How long does it take for a new sales leader to make an impact?
The timeline depends on the business, sales cycle and scope of the role. The first 90 days can establish priorities and operating routines, but measurable revenue outcomes may take longer. Companies should agree on realistic milestones before the person joins.
Conclusion
The decision to hire a sales leader is ultimately a decision about the kind of sales organisation a business wants to build.
Revenue records and professional networks can help identify candidates, but they cannot replace a careful assessment of judgement, leadership behaviour and the ability to reproduce results in a new environment.
Companies improve their chances of making the right appointment when they define the problem clearly, verify achievements, involve the people who will work with the new leader and set realistic expectations from the beginning.
The strongest candidate is not necessarily the person with the most impressive story. It is the person whose experience, approach and leadership qualities match the work the business actually needs done.
