VP of Sales, Health Insurance Vertical

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 VP of Enterprise Sales to lead and grow a team of enterprise sales reps selling our AI-powered SaaS underwriting and analytics solutions to health insurance and

benefits organizations. In this role, you’ll own your team’s pipeline, forecasting, and quota attainment while instilling a consultative selling mindset across the group. The ideal candidate has led or coached sales teams before, brings credibility across the health insurance ecosystem, and has experience rolling out new sales methodologies that actually stick.

They thrive coaching reps through complex, multi-stakeholder deals and are comfortable representing their team’s results to leadership.

How You Will Make an Impact

Recruit, coach, and manage a team of enterprise sales reps, setting clear expectations around pipeline, forecasting, and consultative selling standards Own regional sales targets, ensuring the team hits, achieves, and exceeds monthly and annual quotas, with accurate forecasting and pipeline reporting in Salesforce Conduct regular 1:1s and pipeline reviews with each rep to identify coaching opportunities, remove blockers, and reinforce consultative selling as the standard, not a one-time initiative Lead by example on key deals, stepping into complex or strategic opportunities to model consultative