By Simon Severino, founder of Strategy Sprints, where 2,400+ B2B founders have gone through our programs. Updated November 2026.

Look for a builder, not a star closer: someone who turns your sale into a written process, coaches reps in weekly deal reviews, and leads a sales call with control instead of pitching. Test it in the interview. Let the candidate sell you your own product and watch the order of their questions. Price before pain is a no. 🐬

Get this hire right and you stop being the only closer. Your evenings come back, and your new reps learn a sale that works without you in the room. 🐯

Am I ready to hire a head of sales?

Picture the week your first sales posting goes live. The job ad says "reports to the CEO". That's you. And the whole sales process still lives in your head.

You're ready when three things are true:

1. You can write your sale down on one page. Who buys, why, the steps of the call, what a good deal looks like.
2. You've closed enough deals yourself to know why you win. Not just that you win.
3. There's a team to lead, or one about to start. A head of sales with nobody to coach is an expensive closer.

Hire too early and you pay twice: the salary, and the months your reps spend copying the wrong habits.

If the first one isn't true yet, start there. A leader can sharpen a process. They can't read your mind. Here's how to hire your first salesperson if you're one step earlier. 🌴

What separates a builder from a closer?

A great closer wins deals. A great head of sales makes other people win deals. Different job.

Signs you're talking to a builder:

• They've written a sales playbook before. Ask to see one (with names removed).
• They talk about reps first, deals second. An answer like "both my reps hit target by month four" beats "I closed the biggest deal in company history".
• They've sold at your price point. A $3,000 sale and a $60,000 sale need different skills. Ask what deal size they've led.
• They've built from early stage. Taking over a finished machine at a big company is a different job from building one.
• They run a rhythm. A fixed weekly pipeline review, a scorecard, one priority a week.

How do I test a candidate in the interview?

Don't ask "how would you sell our product?". Make them do it.

Play the buyer. Give them 20 minutes. Then watch the order of what they do:

1. Do they get you talking, mirror your words, and only then lead? (Step 1 Visualize)
2. Do they find your real frustration and what you already tried? (Step 2 Frustration)
3. Do they ask how it fits with everything else on your plate? (Step 3 Importance)
4. Do they ask what happens if you do nothing, then go quiet? (Step 4 Cost of Inaction)
5. Do they let you describe the result in your own words? (Step 5 Deliverables)
6. Do they talk time and people before money? (Step 6 Investment)
7. Do they ask for a start date? (Step 7 Starting Date)
8. Do they offer to put your words on paper? (Step 8 Statement of Work)

These are the 8 Steps of the Repeatable Sale. A candidate doesn't need our names for them. They need the order. Someone who opens with a deck and a price in minute five will teach your reps to do the same. 🐬

Which interview questions reveal the most?

Word for word:

• "Walk me through the last rep you coached from struggling to hitting target. What did you change?"
• "Show me how you'd run our Monday pipeline review. What are the three questions you ask about every deal?"
• "Tell me about a deal you lost after the proposal went out. Where did it really stall?"
• "What would you write down in your first 30 days, and who would you show it to?"
• "When do you step into a rep's deal, and when do you stay out?"

Listen for their answers in specifics: names of steps, numbers they tracked, a rep's real story. Vague answers about "energy" and "relationships" sound fresh in the interview and go stale by month two. 🐯

What are the red flags?

• "I bring my network." A contact list runs out fast. A process doesn't.
• Forecast talk without process talk. They can predict the number but can't explain how a deal moves.
• Discounting stories told as wins. "I got it over the line with a last-minute discount" is a habit your team will copy. It tastes like a win and costs margin on every deal after.
• No questions about your buyers. A builder is curious about who buys and why before they talk about themselves.
• They want to stop doing calls. In a growing company, the head of sales still sells. Player-coach, not spectator.

What should the first 90 days look like?

Agree on it before they sign, in writing:

• Days 1-30: ride along on your calls, write the sale down step by step, show it to you.
• Days 31-60: run the weekly rhythm (Monday Strategy to set the week, Friday Learnings to score it) and coach every rep in a deal review.
• Days 61-90: reps run the written process without you on the call. You check the Friday scorecard, not their calendar.

That's the moment you stop being the only closer, and you feel the weight come off. 🌴

If you do one thing this week: write your sale down on one page, before the job ad goes out.

FAQ

Should my first sales hire be a head of sales? Usually not. Start with a seller who can run a written process. Hire the leader once there's a team to coach.

What's more important, industry experience or sales leadership experience? Leadership of a team at your price point. Industry knowledge comes much faster than the skill of coaching a team.

How do I know if a candidate can coach? Ask them to coach you on a recorded call of yours, live, in the interview. Watch whether they ask questions or lecture.

Should a head of sales still close deals? Yes, while the company is still growing its first team. A player-coach keeps the process honest and shows reps what good looks like.

What if I hire the wrong person? Make the first 90 days a written plan with checkpoints at day 30 and 60. You'll see the gap early and can act on it.

Want the tools, AI skills and a community of founders doing the same work? Join Sprint Club, 7 days free: https://www.strategysprints.com

Ready to accelerate now? Book a Discovery Call: https://calendly.com/strategysprint/discovery-call

Happy hunting.

Simon & The Sprinters 🐬⚡️🐆