Head of Sales

About Endgame

Endgame is building the context engine for go-to-market. The bet underneath the company: the hard part of applied AI isn't the model — it's getting the right context to it. Real enterprise data is messy. Duplicated contacts across seven systems, deals referenced by nickname in Slack, methodology that lives in someone's head. Models can't reason their way out of that. You have to do the work upstream.

So that's what we do. Entity resolution across CRM and conversational data, fact extraction with provenance, retrieval that respects permissions and recency, methodology encoded as first-class structure. The output: a layer that powers both day-to-day GTM work and the agents teams build on top of it — agents that work in production, not just demos. Companies like Monte Carlo, BetterUp, Braze, Hex, and Vistra run their revenue motion on it.

We're a small, technical team solving specific, unsolved problems at the boundary of data engineering and applied AI. If that's the work you want to be doing, we'd like to meet you.

Your Mission

We're looking for our Head of Sales — someone excited to build the function from the ground up. You'll report to our CEO, partnering directly on every dimension of how Endgame goes to market.

Endgame is a platform that serves the whole GTM org, not just sales. The leader we want thinks at that scope: a technical product sold top-down to technical buyers, a co-build motion with engineers in the room, and a buying committee that's cross-functional by default.

Your Responsibilities

Close Endgame's biggest deals yourself – Carry a senior book and run the most strategic enterprise opportunities top-down with the CEO and an FDE.

Help your team close theirs – Coach AEs through their hardest deals, and step in personally when the moment calls for it.

Build the function – Hire and develop senior enterprise AEs against Endgame's consultative, FDE-paired motion.

Codify the playbook – Keep the methodology current as the product, ICP, and buying committee evolve.

Partner with FDE leadership – Own the joint cadence between AEs and FDEs and keep the co-build motion working as a real partnership.

Our Ideal Candidate

You've built an enterprise sales function from zero – Not inherited a team and scaled it, actually built one. Early-stage company, top-down enterprise motion, you on the founding bench.

You sell technical product to technical buyers – Complex software into CIOs, CTOs, VPEs, Heads of Data, or senior technical operators. C-suite selling

experience is acceptable in lieu of a specific persona match; product-specific selling experience is not required.

You've reported to a founder before, ideally more than once – You know what it takes to be a founder's right hand on revenue, and what it costs.

Your career path is non-linear – That's a feature, not a bug.

You coach to a methodology, not just a number – You've shipped a sales

playbook that survived your tenure.

Comfortable in a fast-paced startup environment, adapting quickly and

collaborating across diverse teams.

What probably isn't a fit

Mid-market motion as your primary track record

Non-technical product background

A career pattern of scaling inside an existing structure rather than building from zero

Operating mode that runs outbound onto existing traction (we need someone who can build the engine, not run a play that assumes one already exists)

Short recent tenures

Strongest work several years in the rearview