Enterprise Sales Director - Health

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.
• 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.