VP of Enterprise Sales

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 its 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 selling and build credibility with major accounts
• Own hiring, onboarding, and ramp planning for new reps joining the team
• Identify underperformance early and create improvement plans, while recognizing and developing high performers on the team
• Partner with Marketing, Product, and Customer Success to relay field feedback and help shape regional demand generation and messaging
• Represent the team in leadership forecasting calls and QBRs, providing visibility into regional trends, risks, and opportunities

Skills Needed to Succeed

• 10+ years of enterprise SaaS or technology sales experience, including experience leading, coaching, or mentoring a sales team
• Domain expertise in the health insurance space
• Proven experience hiring, onboarding, and developing sales talent, including identifying and addressing underperformance
• A strong consultative and strategic mindset with prior experience rolling out a new sales process or methodology across a team
• Ideally 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 lead 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 including medical, dental, vision, 401k, paid paternal leave, and more
• Ample opportunities to learn and take on new responsibilities