How to Find a Good Head of Sales:
A Guide for CEOs and Founders

At a certain point in every company’s development, sales cease to be a product issue and become an organizational one. The founder cannot remain the sole salesperson indefinitely—but hiring the wrong person for the Head of Sales role is one of the most costly mistakes a company can make during the scaling phase. It sets the organization back 12–18 months, not just 3. That’s why the decision of when to recruit, who to look for, and how to screen candidates is just as important as the recruitment process itself.

When is a company ready for a Head of Sales—and when isn't it?

The first pitfall most founders fall into is poor timing. Hiring a Head of Sales too early results in the new leader having nothing to work with—no repeatable process, no ICP, no working playbook. Hiring too late means the founder wastes months on sales that should be spent on the product, strategy, and investors.

Four signs that it's time:

• The founder spends over 30% of his time on sales and has no time for anything else
• The company has closed at least a dozen deals using a repeatable process
• The pipeline is growing faster than the organization's capacity to handle it
• The company plans to expand into new geographic markets or segments

It’s just as important to know when the time isn’t right. If the company hasn’t achieved product-market fit, if every deal is different and you don’t know what you’re actually selling—a Head of Sales won’t solve that problem. Before you start looking for a sales leader, make sure you have something that can be scaled.

Head of Sales, Sales Director, VP of Sales — which role are you actually hiring for?

Most founders use these titles interchangeably and start the hiring process with the wrong candidate profile. This wastes weeks of the process and ends up with the hiring of someone who is qualified—but not for that specific role at that specific stage of the company. The three titles represent three completely different sets of responsibilities and require different candidate profiles.

In practice: DoxyChain needed a traditional Head of Sales—someone who could take over sales from the CEO and simultaneously build processes from scratch. Perfect Gym was looking for a profile closer to that of a Sales Director—with experience in sales management at a mature SaaS company with a global reach. Vercom needed a Head of International Sales who straddled these two roles—a strategist who would close the first enterprise deals on their own before building a team. Each of these projects required a completely different sourcing strategy and different screening criteria.

What sets a good Head of Sales apart from a good salesperson

The most common mistake in the briefings we receive from clients: requirements written for a great salesperson, not for a sales leader. These are two completely different things—and it’s rare for the same person to be truly good at both at the same time.

A player-manager, not just a manager. In the early stages of a company, the Head of Sales must close deals themselves—not just manage the team that closes them. A candidate who has spent the last five years managing exclusively without direct sales experience may have serious trouble stepping into a role that requires both. Vercom was looking for exactly this profile: someone who would design an international expansion strategy while personally acquiring the first enterprise clients. The hired candidate had previously built a 7-person business development team and generated 291% year-over-year revenue growth—while simultaneously conducting active outbound sales.

Experience in the sales model, not the industry. A Head of Sales with a track record in FMCG may not be the right choice for a B2B SaaS company with a long sales cycle and a multi-tiered decision-making process on the customer side. Don’t ask about the industry; ask about the model: transactional or enterprise, inbound or outbound, sales-led or product-led growth. Perfect Gym was looking for someone with experience scaling SaaS sales in foreign markets—not just someone who was generally good at sales. The difference is fundamental.

Building from scratch vs. scaling what already exists. These are two completely different skills. Someone who has successfully scaled a 50-person sales department in a mature organization may not be able to establish the first process in a company that lacks one—and vice versa. DoxyChain needed someone with “two sides”: the startup flexibility to work without established structures and the corporate discipline to build processes the company didn’t yet have. That’s an exceptionally rare profile.

Cultural fit with the company’s stage of development. A Head of Sales moving from a large corporation to a 20-person startup often struggles with the lack of structures they previously took for granted—the absence of defined processes, the lack of off-the-shelf tools, and the need to make operational decisions on their own. Conversely, someone with exclusively startup experience may lack the process discipline required in a mature organization with an extensive structure.

10 Questions You Must Ask During an Interview with a Candidate for Head of Sales

Not “Tell me about yourself”—questions that reveal what isn’t visible on a resume. A good Head of Sales answers these questions with specific numbers and examples. A candidate who speaks in generalities doesn’t have a track record of tangible results.

1. What was the biggest deal you closed on your own? Describe it from the initial contact to the signing of the contract.
2. Describe the sales process you built from scratch. What worked, what did you change, and why?
3. What did your pipeline look like 30 days after joining your last company, and what was it like 6 months later?
4. What KPIs do you set for your team, and how do you hold them accountable when someone consistently falls short?
5. Describe a situation where a salesperson seemed great during the interview but didn’t perform well on the job. What did you overlook?
6. How do you develop a go-to-market strategy when entering a new market—where do you start?
7. What will you do during your first 30 days with us? (This question assumes that the candidate has done their homework before the interview.)
8. Where do you see the biggest problem in our current sales process?
9. What CRM tools are you familiar with, and how do you build pipeline reports for management?
10. What motivates you more—closing deals on your own or the results of the team you're building?

The last question is crucial. There is no wrong answer—but the answer reveals whether the candidate is a natural player-manager or a manager who doesn’t like to get back into direct sales. Depending on the company’s stage, you need one or the other—and it’s worth knowing this before you hire, not after.

Why aren't job postings reaching the right candidates?

Candidates for Head of Sales who are actively looking for a job are usually not the best ones. The best ones are already employed, deliver results, and don’t browse job boards. That’s why effective recruitment for this role requires reaching out to the market proactively—not waiting for the market to come to you.

A founder’s own network and referrals are the fastest route if they have a strong network in the industry. Problem: Recommendations are subjective and limited to the founder’s existing network. They overlook candidates outside that network—who are often better. Recommendations from investors and advisors are underrated. A good VC with SaaS experience knows the sales market and can point out specific people—it’s worth asking proactively, rather than waiting for someone to suggest them.

Direct search is the only method that consistently reaches passive candidates. It involves mapping the market, identifying specific individuals who meet the criteria, and initiating direct contact. Vercom couldn’t afford to wait for applications—given the very limited pool of candidates combining experience in global SaaS sales with the ability to build structures from scratch, the only effective approach was active outbound outreach to 94 candidates, 4 of whom made the shortlist—the top 4% of the pipeline.

How much does a Head of Sales earn in Poland in 2026?

The Head of Sales’ compensation consists of three components: base salary, OTE (On Target Earnings—total compensation upon meeting targets), and a potential stock option package. The structure and proportions of these components vary significantly depending on the company’s stage.

Three things to keep in mind when putting together an offer. The OTE must be achievable —a Head of Sales who realizes after three months that the plan is unrealistic will start looking for a new job, not deals. At startups, equity is often more important than base pay —a good candidate who believes in the product may accept lower compensation in exchange for a meaningful stock option package with a clear vesting schedule. The commission structure must be simple —complicated commission systems generate conflicts and demotivate rather than motivate.

The First 90 Days — How to Tell If You’ve Hired the Right Person

This is a question no one asks before hiring, and then asks too late—when six months have passed and it’s unclear whether the problem lies with the candidate, the product, the market, or the fact that the company failed to provide the resources promised during the interview. Three specific milestones allow you to assess this earlier.

The first 30 days. The Head of Sales should conduct at least 20 conversations with current and former clients, review the entire pipeline and history of closed deals, and present a preliminary assessment: what works in the sales process, what doesn’t, and why. If, after 30 days, the candidate does not have this assessment—it’s a sign that they either don’t take the role seriously or aren’t capable of performing it.

The first 60 days. A proposal for changes to the sales process should be ready, complete with specific success metrics, a defined or updated ICP, and the first draft of the sales playbook. During this time, the Head of Sales should also close or significantly accelerate at least 2–3 deals from the inherited pipeline.

The first 90 days. The first measurable results: changes in conversion rates at each stage of the funnel, changes in average deal size or sales cycle length, and the first hires to the team if that was part of the role. Not “building relationships” or “getting to know the company”—specific numbers that show the direction.

Summary

Hiring a Head of Sales is one of the most critical HR decisions when scaling a company. The right person in this role accelerates growth, establishes processes that function independently of the founder, and recruits additional salespeople. The wrong person, on the other hand, sets the organization back a year or more and demotivates the entire sales department.

Key takeaways: Define exactly which role you need—Head of Sales, Sales Director, or VP of Sales. Look for a player-manager, not just a manager. Verify their experience within your specific sales model, not just within the industry. And don’t count on the right candidate to stumble upon your job posting on their own— the best Heads of Sales aren’t looking for a job. You have to reach out to them.