Senior Director of Client Success and Innovation, ASO

Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and attainable 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

The Senior Director of Client Success and Innovation, ASO, will lead strategic partnerships with Sidecar Health’s most complex, national employer groups. Reporting directly to the Market President, ASO, this highly visible and high-impact role will serve as the senior-most point of contact for our largest clients, ensuring exceptional delivery, retention, and long-term success.

This is a senior-level, individual contributor role with the opportunity to build and lead a team over time. The ideal candidate will bring deep ASO (Administrative Services Only) experience, strategic problem-solving skills, and a passion for transforming healthcare delivery for large employer groups.

What You’ll Do

• Serve as the executive relationship lead for national and strategic employer clients, driving long-term partnership success and delivering best-in-class client experiences
• Develop and execute strategic account plans focused on engagement, innovation, and measurable value creation
• Provide consultative guidance on plan performance, benefits strategy, and optimization opportunities for self-funded health plans
• Act as a trusted advisor to clients and brokers, clearly articulating Sidecar Health’s model, differentiated value proposition, and evolving capabilities
• Identify opportunities for innovation, product integration, and service enhancements to support client goals and improve the member experience
• Collaborate cross-functionally with Member Care, Clinical, Operations, Product, and Leadership teams to ensure flawless execution and delivery
• Represent the voice of the client within Sidecar Health to inform internal strategies, roadmaps, and priorities
• Monitor and report on key performance metrics, ensuring consistent delivery against SLAs and client expectations
• Lead renewal and growth conversations, proactively identifying and mitigating risks to long-term success
• Partner with the Market President and other leaders to shape the future of the ASO segment, including the potential to build a broader client success team

What You’ll Bring 

• 10+ years of experience in client success, account management, or consulting within health insurance or healthcare services, with a focus on national or jumbo employer groups
• Proven success managing complex, self-funded clients in an ASO model
• Executive presence with outstanding client-facing communication and strategic advisory skills
• Ability to navigate ambiguity, influence cross-functionally, and execute in a fast-paced, high-growth environment
• Passion for innovation and reimagining the healthcare client experience
• Demonstrated ability to lead without authority, with the potential to build and mentor a team
• Strong understanding of healthcare cost containment strategies, network models, and member engagement tactics
• Bachelor’s degree required

What You'll Get

• Competitive salary, bonus opportunity, 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.