Head of Revenue

Join the Team Redefining How Sponsorship Is Measured

At Trajektory, we’re not just building software, we’re reshaping an industry. Sponsorship is one of the largest marketing channels in the world, yet most brands still can’t quantify what they’re getting for their investment. Our platform brings clarity, accountability, and intelligence to sponsorship, helping brands, teams, and agencies measure exposure and impact across TV, social, and digital.

Today, half of all teams in the NFL, NBA, MLB, and MLS use Trajektory and we’re just getting started.

Why Trajektory

Trajektory is built by people who love data, sports, and solving hard problems. We care about curiosity, integrity, and working with good humans.

You’ll join a small, high-impact team where your ideas shape the product, your work is visible, and your growth accelerates alongside ours.

The Role

We’ve built the product and landed the logos, now we’re scaling.

As Head of Global Revenue, you’ll lead and evolve our go-to-market engine, coach a talented team, and bring operational rigor to how we sell and grow. This is a player-coach role for someone who can both close strategic deals and build the systems that make success repeatable.

What You’ll Do

Lead the Team

● Coach and mentor 3-4 quota-carrying reps.

● Drive pipeline discipline, forecasting accuracy, and accountability.

Drive Growth

● Own the revenue roadmap, comp plans, and territory design.

● Define and refine ICPs across brands, agencies, and sports properties.

● Partner with marketing and product on demand generation and positioning.

Build Process and Clarity

● Maintain clean CRM data and forecasts.

● Report clearly to execs and the board on pipeline health.

● Use analytics to improve win rates and deal velocity.

Collaborate Cross-Functionally

● Align with Marketing, Product, and Customer Success on GTM, pricing, and renewals.

● Feed customer and market insights into strategy and product direction.

You’ll Thrive Here If You...

● Have scaled B2B SaaS revenue from early adopters to enterprise scale

● Have sold analytics or data-driven platforms to marketing leaders.

● Love building process, coaching teams, and creating structure that scales.

● Lead with integrity, curiosity, and empathy.

● Are Chicago-based (or open to relocation) and thrive in a hybrid culture.

Why Now

We’ve achieved product-market fit, landed major clients, and have strong board support. The opportunity is clear. What’s missing is you, a leader ready to scale smartly, drive clarity, and build a repeatable, healthy GTM motion.

If that sounds like your kind of challenge, let’s talk.