Head of Sales

About Endgame

Endgame is creating the context layer for go-to-market teams. The company’s core idea is that successful applied AI depends less on the model itself and more on feeding it the right context. In enterprise environments, data is often fragmented and inconsistent: contacts are duplicated across multiple systems, deals are referred to by informal names in Slack, and critical methodology may exist only in people’s heads. Endgame tackles those upstream problems so models can actually reason effectively.

Its platform handles entity matching across CRM and conversational data, extracts facts with traceability, retrieves information while honoring permissions and freshness, and turns methodology into structured, reusable logic. This supports both everyday GTM work and production-ready agents built on top of the system. Customers such as Monte Carlo, BetterUp, Braze, Hex, and Vistra use it to power their revenue operations.

The team is small and highly technical, focused on solving specific open problems at the intersection of data engineering and applied AI. If that kind of work excites you, the company would like to connect.

Your Mission

Endgame is hiring a Head of Sales to build the sales function from scratch. The role reports directly to the CEO and works alongside them across the full go-to-market motion.

This is a platform used by the entire GTM organization, not just the sales team. The ideal leader understands that scope: a technical product sold from the top down to technical decision-makers, a co-building sales motion that includes engineers in live deal work, and a buying group that is cross-functional by nature.

Key Responsibilities

• Own the largest enterprise opportunities personally, carrying a senior pipeline and leading the most strategic top-down deals with the CEO and an FDE.
• Support the team in closing their deals by coaching AEs through complex opportunities and stepping in directly when needed.
• Build and grow the sales organization by hiring and developing senior enterprise AEs aligned to Endgame’s consultative, FDE-partnered approach.
• Refine and document the sales methodology so the playbook stays relevant as the product, ICP, and buying committee change.
• Work closely with FDE leadership to manage the shared cadence between AEs and FDEs and keep the co-build model operating as a genuine partnership.

Ideal Candidate Profile

The company is looking for someone who has truly created an enterprise sales function from the ground up, not someone who only inherited and expanded an existing team. The right background includes early-stage startup experience, a top-down enterprise motion, and a role on the founding revenue team.

You should be comfortable selling technical products to technical audiences such as CIOs, CTOs, VPEs, Heads of Data, or other senior technical operators. Experience selling to the C-suite is also acceptable, even if the exact persona differs. Prior product-specific sales experience is not required.

The preferred candidate has reported directly to a founder before, ideally more than once, and understands the expectations and tradeoffs of being a founder’s key revenue partner. A non-linear career path is welcomed, not penalized.

They should also be able to coach to a repeatable methodology rather than only manage to quota, and should have created a sales playbook that remained useful beyond their own tenure. Comfort in a fast-moving startup environment, plus the ability to adapt quickly and work across varied teams, is important.

Benefits

• Competitive pay plus equity participation
• 401(k) retirement plan, along with health, dental, and vision coverage
• Flexible paid time off
• Paid parental leave
• Education stipend

Application Notes

The listed qualifications are intended as guidance rather than hard gates. Candidates are not expected to match every requirement. If your background and strengths make you a strong fit, the team encourages you to apply or contact the hiring team directly.