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
• 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, and benefits administration
• Strategic thinker with the ability to balance long-term vision and short-term execution
• Experience in a high-growth, entrepreneurial environment is a plus

What You'll Get

• Competitive salary, uncapped incentive bonus, and equity package
• Comprehensive Medical, Dental, and Vision benefits
• A 401k retirement plan
• Paid vacation and company holidays
• Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S.

Qualifications

• Bachelor's degree required

Benefits

• Comprehensive Medical, Dental, and Vision benefits
• A 401k retirement plan
• Paid vacation and company holidays

Schedule

• Full-time

Pay

• Competitive salary, uncapped incentive bonus, and equity package

Company Information

Sidecar Health is an Equal Opportunity employer committed to building a diverse team. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status or disability status.