How to hire a head of sales in real estate without wasting six months

Article by Evgeny Kazimirsky — co-founder RED x RED Experts.

You need to understand that a head of sales is not your best salesperson on the team. It is someone who knows how to build a system and deliver results through other people.

A good sales manager delivers results personally, while a head of sales makes sure the whole team delivers them.

These are different skills, and one does not automatically follow from the other.

What a strong head of sales should actually be able to do:

• Own the revenue — hitting the plan, growing the department, understanding unit economics
• Build the team — hire, onboard, train, retain strong performers and part ways with weak ones in time
• Work systematically — CRM, KPIs, reports, forecasting
• Manage people — mentoring, discipline without toxicity, team development

The hiring funnel: three stages you cannot skip

Stage 1 — Resume screening

Look at the numbers, not the words. A strong resume contains specifics: team growth, revenue growth, implemented processes. If you remove the job title, the text should still make it clear that the person actually managed sales.

What should raise concerns: no metrics, focus only on personal sales, lots of motivational phrases, changing jobs every 6 months.

Red flags: an “inspiring leader” without numbers, no hiring experience, unable to talk about analytics, blames managers for weak results.

Stage 2 — Meeting with the recruiter

After the meeting — always a recording, a transcript and a written summary. The recruiter must know how to prepare one. This is not a formality: the summary helps the hiring manager make a balanced decision instead of relying on first impressions.

Stage 3 — Meeting with the hiring manager

In a small company (5–10 people in the sales department) this is the founder; in a large one — the commercial director. This is the person who makes the final decision.

7 questions you must ask at the interview:

• How did you build your team? How many people did you personally hire?
• Which metrics did you track?
• Which conversion metrics did you improve and how?
• What do you do with weak managers?
• How do you forecast sales?
• What does your onboarding for new managers look like?

Boutique vs systematic: who exactly do you need

At the screening stage, just as when hiring a broker, it is essential to define in detail why exactly you need a head of sales.

In a small sales department, the head of sales must be able to work with each manager deeply and individually — this is the boutique approach. In a large department, you need a different profile: someone who can build a system, delegate, and manage adjacent functions — quality control, analytics, qualification.

These are different people with different skill sets. Decide clearly who you need before launching the hiring funnel.

Why it is hard to hire a good head of sales on the first try

The stronger the player you are looking for, the harder it is to hire them. A $1,000 qualifier is easy to find — many have passed through your hands, you understand what they do. A manager is harder. A head of sales is even harder, because it is a different level of personality and a different skill set.

You must understand the candidate's level: some lack strong skills but know how to push, while others are softer but very strong in terms of skills.

Two criteria matter here: the head of sales must fit your team, and they must fit the leadership style of the person they report to.

If you are hiring a head of sales for the first time, your first attempt will most likely fail. That is normal, but expensive: hiring and onboarding usually take 3 months, but if the person does not “click” with your team, you have to hire and onboard a new one, which ends up taking 6 months. To succeed on the first try, you need an expert who has already hired heads of sales and knows what a strong candidate looks like.

How it worked for us. I had an advisor from a company significantly larger than ours with extensive experience in real estate sales. We built a four-stage funnel: resume → recruiter → me → a final meeting with the partners and the advisor. At the final stage, the advisor asked questions in the areas I might have missed. It saved us months.

Onboarding: the first three months decide everything

Onboarding a head of sales takes 1 to 3 months. Here is what those months should look like:

Month 1 — Immersion. The head of sales fully takes over their responsibilities and builds their workflow. 70% of their calendar is recurring activities: one-on-one meetings with managers, deal reviews, training. Your task is to watch how quickly they grasp the context.

Month 2 — Operational results. The head of sales must deliver results in the form of concrete changes: written playbooks, implemented analytics, configured processes. You should see momentum — the department moving in the right direction.

Month 3 — Financial performance. You should set a revenue target for this month or for all three. Then look at the numbers and make the final decision.

If after 2 weeks the person clearly cannot cope — take note. If by the end of the second month the operational tasks are not done — that is a signal. If by the end of the third month they are far from the financial plan — it is most likely time to part ways.

The key quality of a leader is the ability to let people go

The most valuable skill — both in you as the employer and in the head of sales — is the ability to part ways in time with those who cannot cope (while doing it respectfully) and to hire stronger people in their place. Do not give yourself false hope, and judge the head of sales just as strictly: do they let go of those who need to be let go, or do they keep people out of pity?

A team does not grow when you hire good people. It grows when you know how to filter them out.