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Enterprise Sales Director – Health
Gradient AIEnterprise Sales Director leading sales efforts in health insurance ecosystem. Selling AI-powered SaaS underwriting and analytics solutions to health insurance and benefits organizations.
About the role
Key responsibilities & 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.
Requirements
What you’ll need- 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.
Benefits
Comp & perks- A fun, team-oriented startup culture.
- Generous stock options - we all get to own a piece of what we’re building.
- Unlimited vacation days.
- 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.
ATS Keywords
✓ Tailor your resumeApplicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard Skills & Tools
enterprise SaaS salessolution designROI modelingcontract negotiationpipeline reportingtechnical demosquota attainment
Soft Skills
negotiation skillspresentation skillscommunication skillsself-drivencollaborativeability to work in ambiguityhunter mentality
Certifications
Bachelor's degree