Enterprise Sales Director - Health New

About the Role: We are searching for a results‑driven Enterprise Sales Director – Health to 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. The role requires a deep understanding of the health insurance landscape and the ability to speak the language of underwriting, actuarial, and clinical leadership.

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 Bachelor’s degree required; 10+ years of enterprise SaaS or technology sales experience, with at least 5 years selling into the health insurance space. Demonstrated ability to build and close a book of business from scratch; a hunter mentality with proven quota attainment at or above 100%. Strong negotiation and presentation skills; experience running technical demos and building ROI models tailored to health insurance and benefits stakeholders. Prior experience navigating complex buying committees, including Chief Actuaries, CMOs, VPs of Underwriting, and CFOs at health carriers and benefits organizations; outstanding verbal and written communication skills. Ability to work in a self‑driven manner within a fast‑paced, collaborative startup environment; comfort with ambiguity and a bias toward action.

What We Offer: A fun, team‑oriented startup culture. Generous stock options – we all get to own a piece of what we’re building. Flexible schedule that supports working from home. Full benefits package includes medical, dental, vision, 401k, paid paternal leave, and more. Ample opportunities to learn and take on new responsibilities. OTRange: The anticipated on‑target earnings (OTE) for this position is $400,000 – $450,000 USD, inclusive of base salary with strong accelerators. We are an equal opportunity employer.