VP, Sales & Account Management

Join Us!

HealthCare.com has become one of America’s fastest-growing insurtech companies, revolutionizing how consumers shop for health insurance. Leveraging advanced technology and data science, the company has developed customized proprietary products to better fit consumer requirements, enhance customer satisfaction, and take some of the guesswork and inefficiencies out of buying insurance.

Pivot Health, a subsidiary of HealthCare, Inc., is a high-growth health insurance distribution company specializing in Short-Term Medical (STM), Fixed Indemnity, and ancillary health products. We operate in a dynamic, start-up-oriented environment and are expanding rapidly as market conditions — including ACA subsidy changes and a projected 9–10 million individual market exits — create significant demand for our product portfolio.

About The Role

The VP, Sales & Account Management is a newly created, senior leadership role that will own and drive all broker sales and account management activity for Pivot Health. Reporting directly to the President, this executive will build and lead a high-performance team, establish new business development discipline, and deepen relationships across our broker and consultant distribution channels.

This is a hands-on leadership role for someone who thrives in a fast-paced environment, can operate both strategically and tactically, and is ready to make an immediate impact.

What You'll Do

• Sales Leadership & Revenue Growth
• Own the broker and consultant distribution sales strategy, with accountability for revenue targets across non-owned channels
• Transition the sales organization from a reactive account management model to a proactive hunter/farmer structure
• Recruit, onboard, and scale new broker and FMO relationships to expand Pivot's active distribution footprint
• Drive new business development with independent agents, general agents, and field marketing organizations (FMOs)
• Represent Pivot Health at industry events, carrier partner meetings, and key broker/consultant forums
• Account Management & Retention
• Lead and develop the Account Management team, ensuring existing broker relationships are nurtured, productive, and growing
• Establish SLAs, performance metrics, and accountability frameworks for the AM team
• Partner with internal operations and member services to resolve broker escalations and improve the end-to-end broker experience
• Develop and execute a tiered broker engagement model (key account vs. general book)
• Team Building & Culture
• Hire, coach, and develop a team of BDMs and Account Managers; establish clear roles, comp structures, and performance expectations
• Create a winning team culture grounded in accountability, collaboration, and results
• Work cross-functionally with marketing, operations, and product to align distribution strategy with company priorities
• Strategy & Reporting
• Contribute to the company's Growth Roadmap and quarterly operating plan (Rocks) as a key member of the leadership team
• Provide regular pipeline, forecast, and performance reporting to the President
• Identify market trends, competitive dynamics, and channel opportunities to inform product and pricing decisions
• Who You Are
• 10+ years of progressive sales and account management experience in the health insurance distribution space
• Deep, established relationships with brokers, general agents, and/or consultants in the individual and small group health market
• Demonstrated success building and leading sales teams in a growth-stage or entrepreneurial environment
• Track record of hitting and exceeding revenue targets in a quota-carrying or team leadership capacity
• Strong understanding of the U65 / non-ACA insurance market, distribution economics, and broker compensation structures
• Self-starter with the ability to hit the ground running — comfortable operating without a fully built infrastructure
• Excellent communicator, collaborator, and relationship builder across internal and external stakeholders
• Preferred / Strong Plus
• Experience with Short-Term Medical (STM) products and distribution
• Background in ancillary health products: dental, vision, accident, critical illness, or fixed indemnity
• Familiarity with FMO/IMO recruiting and management
• Experience managing or transitioning TPA/carrier partner relationships
• Prior work in a start-up, scale-up, or private equity-backed health business