Head of GTM

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.

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 , 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.

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, Rev Ops 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.

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.

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

We already have the beginnings of a different model.

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.

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.

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…