VP of Strategic Accounts

About the Role

Sidecar Health is transforming how employers and their members experience healthcare — through transparent cash pricing, no provider networks, and meaningful cost savings. As we accelerate our enterprise growth, we are looking for a VP of Strategic Accounts to lead that charge. Reporting directly to the CEO, this individual will own our enterprise sales strategy and execution at a pivotal moment for the company, with a pipeline of national accounts already in active evaluation.

What You'll Do

• Develop and execute a comprehensive enterprise sales strategy to drive new business growth
• Set and achieve ambitious revenue targets, with a focus on net-new client acquisition
• Identify and pursue opportunities within jumbo and national employer groups
• Build and scale a repeatable, high-performing sales process
• Build and maintain strong relationships with brokers, consultants, and enterprise employer clients
• Partner with clients to understand their unique needs and work with internal teams to tailor solutions accordingly
• Serve as a trusted advisor on health plan solutions and benefits strategy
• Stay informed about industry trends, competitor offerings, and regulatory changes
• Collaborate with product and marketing teams to refine offerings based on market feedback and client insights
• Partner with finance, operations, and member experience teams to ensure seamless client onboarding and ongoing support
• Provide input on pricing strategies, service enhancements, and value propositions

What You'll Bring

• 10+ years of experience in health insurance or employee benefits sales, with a strong focus on jumbo/national employer groups
• Proven track record of securing enterprise clients and driving significant revenue growth
• Strong network within the broker/consultant community and with benefits leaders at large organizations
• Exceptional communication, negotiation, and relationship-building skills
• Deep understanding of health plan products, self-funded and ASO models