Enterprise Sales Director - Health

About this role

This is a fully remote opportunity.

Gradient AI:

Gradient AI is revolutionizing Group Health and P&C insurance with AI-powered solutions that help insurers predict risk more accurately, improve profitability, and automate underwriting and claims. Our SaaS platform taps into one of the industry’s largest data lakes—tens of millions of policies and claims—to deliver deep, actionable insights. Trusted by leading carriers, MGAs, TPAs, and self-insured employers, Gradient AI has grown rapidly since our founding in 2018. Backed by $56M in Series C funding, we're scaling fast—and it's an exciting time to join the team.

About the Role:

We are searching for a results-driven Enterprise Sales Director – Health to join our growing team and lead enterprise sales efforts across the health insurance ecosystem. This individual will own the full sales cycle, selling our AI-powered SaaS underwriting and analytics solutions to health insurance and benefits organizations. This role requires someone who understands the nuances the health insurance landscape and can credibly speak the language of underwriting, actuarial, and clinical leadership.

The ideal candidate brings deep relationships across the health insurance ecosystem and a proven track record of closing complex, multi-stakeholder enterprise deals. They are equally comfortable presenting to a Chief Actuary and negotiating with key leadership across large enterprise organizations, and they thrive in a high-growth startup environment where they can build something meaningful.

How you will make an impact:

• Own and grow a pipeline of enterprise opportunities across the group health ecosystem through strategic prospecting, existing relationships, and referral networks

• Lead the full consultative sales cycle from discovery and needs assessment through solution design, ROI modeling, contract negotiation, and close—engaging underwriting, actuarial, and C-suite stakeholders throughout

• Craft compelling statements of work, pricing proposals, and executive-level business cases that clearly articulate Gradient AI’s value to health plan and benefits decision-makers

• Develop deep domain expertise in AI-powered underwriting and stop loss analytics, and clearly communicate how our solutions drive loss ratio improvement, operational efficiency, and portfolio growth for health insurance clients

• Hit, achieve, and exceed monthly and annual sales targets; provide accurate forecasting and pipeline reporting in CRM

Skills needed to succeed:

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