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Enterprise Sales Director - Health

June 2, 2026

This is a fully remote opportunity. Gradient AI: 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. 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. About the Role: 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. 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. How you will make an impact: <ul> <li>Own and grow a pipeline of enterprise opportunities across the group health ecosystem through strategic prospecting, existing relationships, and referral networks </li> <li>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 </li> <li>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 </li> <li>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 </li> <li>Hit, achieve, and exceed monthly and annual sales targets; provide accurate forecasting and pipeline reporting in CRM </li> </ul> Skills needed to succeed: <ul> <li>Bachelor’s degree required; 10+ years of enterprise SaaS or technology sales experience, with at least 5 years selling into the health insurance space </li> <li>Demonstrated ability to build and close a book of business from scratch; a hunter mentality with proven quota attainment at or above 100% </li> <li>Strong negotiation and presentation skills; experience running technical demos and building ROI models tailored to health insurance and benefits stakeholders </li> <li>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 </li> <li>Ability to work in a self-driven manner within a fast-paced, collaborative startup environment; comfort with ambiguity and a bias toward action </li> </ul> What We Offer: <ul> <li>A fun, team-oriented startup culture. </li> <li>Generous stock options - we all get to own a piece of what we’re building. </li> <li>Unlimited vacation days. </li> <li>Flexible schedule that supports working from home. </li> <li>Full benefits package includes medical, dental, vision, 401k, paid paternal leave, and more. </li> <li>Ample opportunities to learn and take on new responsibilities. </li> </ul> 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. 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.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...