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About the role
<p><strong><em><span data-contrast="auto">This is a fully remote opportunity.</span></em></strong></p>
<p><strong><span data-contrast="auto">Gradient AI: </span></strong><span data-contrast="auto"> </span><span data-ccp-props="{}"> </span></p>
<p><span data-contrast="auto"> 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. </span><span data-contrast="auto">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.</span><span data-ccp-props="{"134233117":false,"134233118":false,"335551550":0,"335551620":0,"335559738":240,"335559739":240}"> </span></p>
<p><strong><span data-contrast="auto">About the Role: </span></strong><span data-contrast="auto"> </span><span data-ccp-props="{}"> </span></p>
<p><span data-contrast="auto">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.</span><span data-ccp-props="{"134233118":false,"335559739":160}"> </span></p>
<p><span data-contrast="auto">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.</span><span data-ccp-props="{"134233118":false,"335559739":160}"> </span></p>
<p><strong><span data-contrast="auto">How you will make an impact:</span></strong><span data-ccp-props="{}"> </span></p>
<ul>
<li><span data-contrast="auto">Own and grow a pipeline of enterprise opportunities across the group health ecosystem through strategic prospecting, existing relationships, and referral networks</span><span data-ccp-props="{"134233117":false,"134233118":false,"335559738":0,"335559739":0}"> </span></li>
<li><span data-contrast="auto">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</span><span data-ccp-props="{"134233117":false,"134233118":false,"335559738":0,"335559739":0}"> </span></li>
<li><span data-contrast="auto">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</span><span data-ccp-props="{"134233117":false,"134233118":false,"335559738":0,"335559739":0}"> </span></li>
<li><span data-contrast="auto">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</span><span data-ccp-props="{"134233117":false,"134233118":false,"335559738":0,"335559739":0}"> </span></li>
<li><span data-contrast="auto">Hit, achieve, and exceed monthly and annual sales targets; provide accurate forecasting and pipeline reporting in CRM</span><span data-ccp-props="{"134233117":false,"134233118":false,"335559738":0,"335559739":0}"> </span></li>
</ul>
<p><span data-contrast="auto"> </span><strong><span data-contrast="auto">Skills needed to succeed: </span></strong><span data-contrast="auto"> </span><span data-ccp-props="{}"> </span></p>
<ul>
<li><span data-contrast="auto">Bachelor’s degree required; 10+ years of enterprise SaaS or technology sales experience, with at least 5 years selling into the health insurance space</span><span data-ccp-props="{"134233117":false,"134233118":false,"335559738":0,"335559739":0}"> </span></li>
<li><span data-contrast="auto">Demonstrated ability to build and close a book of business from scratch; a hunter mentality with proven quota attainment at or above 100%</span><span data-ccp-props="{"134233117":false,"134233118":false,"335559738":0,"335559739":0}"> </span></li>
<li><span data-contrast="auto">Strong negotiation and presentation skills; experience running technical demos and building ROI models tailored to health insurance and benefits stakeholders</span><span data-ccp-props="{"134233117":false,"134233118":false,"335559738":0,"335559739":0}"> </span></li>
<li><span data-contrast="auto">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</span><span data-ccp-props="{"134233117":false,"134233118":false,"335559738":0,"335559739":0}"> </span></li>
<li><span data-contrast="auto">Ability to work in a self-driven manner within a fast-paced, collaborative startup environment; comfort with ambiguity and a bias toward action</span><span data-ccp-props="{"134233117":false,"134233118":false,"335559738":0,"335559739":0}"> </span></li>
</ul>
<p><strong><span data-contrast="auto">What We Offer:</span></strong><span data-contrast="auto"> </span><span data-ccp-props="{}"> </span></p>
<ul>
<li><span data-contrast="auto">A fun, team-oriented startup culture. </span><span data-ccp-props="{}"> </span></li>
<li><span data-contrast="auto">Generous stock options - we all get to own a piece of what we’re building. </span><span data-ccp-props="{}"> </span></li>
<li><span data-contrast="auto">Unlimited vacation days. </span><span data-ccp-props="{}"> </span></li>
<li><span data-contrast="auto">Flexible schedule that supports working from home. </span><span data-ccp-props="{}"> </span></li>
<li><span data-contrast="auto">Full benefits package includes medical, dental, vision, 401k, paid paternal leave, and more. </span><span data-ccp-props="{}"> </span></li>
<li><span data-contrast="auto">Ample opportunities to learn and take on new responsibilities. </span><span data-ccp-props="{}"> </span></li>
</ul>
<p><span data-contrast="auto">We are an equal opportunity employer.</span><span data-ccp-props="{}"> </span></p>
<p><strong><span data-contrast="auto">OTE Range: </span></strong><span data-contrast="auto">The anticipated on-target earnings (OTE) for this position is $400,000 – $450,000 USD, inclusive of base salary with strong accelerators.</span><span data-ccp-props="{}"> </span></p>
<p><span data-contrast="auto">This role is also eligible for commission, equity grant and a comprehensive benefits package. In accordance with the Massachusetts Pay Transparency Law, we are providing a good-faith salary range for this position at the time of posting. The actual salary offered will depend on the level at which the candidate is hired, as well as their experience, skills, qualifications, and location. Compensation may grow over time through promotions and company-wide adjustments. If your salary expectations fall outside this range, we still encourage you to apply so we can have a conversation. </span><span data-ccp-props="{}"> </span></p>
Perks & benefits
- 401k
- Medical Insurance
- Unlimited Vacation
- Equity Compensation
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