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.
We are an equal opportunity employer.

OTE Range: The anticipated on-target earnings (OTE) for this position is $400,000 – $450,000 USD, inclusive of base salary with strong accelerators.

Skills Required
Bachelor's degree required; 10+ years of enterprise SaaS or technology sales experience
at least 5 years selling into the health insurance space
Demonstrated ability to build and close a book of business from scratch
Strong negotiation and presentation skills
Prior experience navigating complex buying committees