Head of Enterprise Sales

Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and accessible for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen.

The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent.

If you want to use your talents to transform healthcare in the United States, come join us! 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 Head of Enterprise Sales 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, 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
• Bachelor's degree required

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.

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.