Head of GTM - Pitstop

Help create the global standard for sales excellence — and build the GTM engine that takes it to market.

Pitstop is hiring a Head of GTM.

We are beginning the search ahead of our Seed funding round. This will be one of the most important hires we make, so we are prepared to take our time to find someone exceptional.

This is a hands‑on player‑builder role for someone who wants to build a global GTM function, not inherit one.

About Pitstop

Pitstop is the Continuous Sales Coaching company.

Our mission is to enable every salesperson to reach their full potential.

Our vision is to create the global standard for sales excellence .

We help salespeople practice, get coached and objectively measure how they are improving, continuously.

If we succeed, “What’s your Rep Score?” could become a question people across the sales industry instinctively understand.

We are still early, as you would expect at this stage. But the product is live and more than 10 organizations are already using Pitstop across free and paid deployments.

Don’t just take our word for it.

Go to takeapitstop.com , click Try Now and experience Pitstop yourself.

Start with a sales role‑play. Then upload a transcript from a real sales conversation to get your Rep Score and see where Pitstop believes you can improve.

The Role

Today, Pitstop’s GTM is highly founder‑led.

Your job is to change that.

You will build the GTM engine that proves Pitstop can become a major company: winning customers, establishing repeatability and creating strong customer evidence.

Your success will be measured by whether we establish genuine market traction, repeatability and customer evidence. If we do that, Series A should follow.

Initially, you will be extremely hands‑on.

You will open doors, run discovery, demo Pitstop, build relationships, negotiate, close customers, test positioning and pricing, work closely with product, develop partnerships and coach people.

As we grow, you will recruit the team around you.

Ultimately, you will be responsible for GTM across sales, marketing, partnerships, RevOps and customer success.

You will report directly to our CEO, who previously led product at Headspace, sit on the Pitstop leadership team and be the executive responsible for GTM.

Why Join Pitstop?

You will join early enough to shape almost everything about GTM, but far enough along that there is already a live product, early customers, market demand, a clear point of view and a growing audience of sales leaders.

You will have the opportunity to:

• Build GTM from scratch.
• Work directly with the founders and leadership team.
• Recruit and lead the GTM organization.
• Help establish Continuous Sales Coaching as a category.
• Help create the first global standard for measuring and improving sales performance.
• Influence the product directly through what you learn from customers.
• Participate meaningfully in the value you help create.

The package will include a competitive base salary, performance‑related compensation and share options .

Pitstop is fully distributed today, with team members in Seattle, Dublin, the UK and Poland. We are flexible on location for the right person.

Building GTM Differently

We do not want our growth engine to depend primarily on sending more outbound emails.

We already have the beginnings of a different model.

AI GTM Lab

is our top‑of‑funnel engine. Leading GTM operators share practical ways they are using AI, helping us build an audience and relationships with senior sales leaders around the world.

freemium product

creates another potential engine. We believe individual salespeople experiencing Pitstop, getting value from it and spreading it internally can create bottom‑up adoption.

Your job is to prove how effectively that converts into team and company‑wide deployments.

Alongside those motions will be direct selling, partnerships and whatever else the market proves works.

The objective is not to copy somebody else’s GTM playbook. It is to build the one that works for Pitstop.

Who We Sell To

Our focus is B2B companies with meaningful sales organizations.

Today, we are engaging with companies from roughly 20 salespeople upwards. As Pitstop grows, we expect our minimum customer size to increase.

Our economic buyers are typically CROs and RevOps leaders. Sales managers are important champions.

Part of your role will be identifying where the strongest market pull exists, sharpening our ICP and turning that into a repeatable commercial motion.

What You’ll Own

You will:

• Build and execute Pitstop’s GTM strategy.
• Personally win strategic customers.
• Move us from founder‑led selling towards a repeatable sales motion.
• Refine ICP, positioning, pricing and packaging based on market evidence.
• Develop AI GTM Lab as a top‑of‑funnel engine.
• Build partnerships and other scalable distribution channels.
• Ensure customer learning feeds directly into product.
• Establish RevOps and customer success disciplines as we scale.
• Recruit, coach and lead the GTM organization.

Who We’re Looking For

We are looking for a player‑builder.

You will probably have:

• Built GTM inside a high‑growth B2B tech or AI company.
• Personally sold complex technology to senior commercial leaders.
• Experience selling into larger, multi‑stakeholder organizations.
• Helped move a company from founder‑led selling towards a repeatable GTM motion.
• Carried a number recently enough that selling is still instinctive.
• Strong commercial judgment across positioning, pricing, pipeline and closing.
• Operated successfully without large teams or extensive infrastructure.
• A strong bias towards action.
• The ability to represent Pitstop externally with senior sales leaders.
• An international outlook, ideally including experience selling into the US.

We care more about what you have built than the prestige of the companies on your CV.

Sell. Coach. Be Coached.

This is fundamental.

You should have a proven ability to make both salespeople and sales managers better.

You can diagnose where someone is struggling, give specific feedback and help them improve — not simply inspect their numbers.

And you need to be coachable yourself.

We believe great sales leaders should be able to sell, coach and be coached .

We need to practice what we preach.

Sales Excellence Starts With Who You Hire

There is little point investing heavily in onboarding, training and coaching if you hire average salespeople, or people who are not coachable, in the first place.

One example of the demand we are seeing is companies using Pitstop’s custom sales role‑plays during their hiring process.

Instead of relying on CVs and interviews alone, they can see how someone actually sells, and how coachable they are, before hiring them.

We believe hiring is the starting point for sales excellence, not a separate problem.

How We Hire

We practice what we preach.

Shortlisted candidates will complete a custom Pitstop sales role‑play.

We want to see how you actually sell, not simply hear about how you sold in the past.

We will also assess how you coach salespeople and sales managers, and how you respond to coaching yourself.