Head of Account Management

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

We are seeking a strategic and data-driven Head of Account Management to lead and scale our account management function across Georgia, Ohio, and Florida. This role will oversee our two Directors of Account Management, driving strategy, team development, and operational excellence to ensure proactive client engagement and long-term retention. The ideal candidate is an analytical leader with experience in workforce planning, optimizing account management processes, and shifting teams from a reactive to a proactive approach. They will play a key role in strengthening client relationships, improving service delivery, and ensuring scalable growth.

What You’ll Do

• Define and implement the overarching account management strategy, ensuring scalability and efficiency as we expand in GA, OH, and FL
• Provide strategic leadership to the Account Management team, mentoring the two Directors and ensuring their teams are aligned on best practices and proactive client engagement
• Shift the team from a reactive stance to a proactive, value-driven engagement model, focusing on long-term client retention and success
• Assess team capacity, resource allocation, and hiring needs to ensure optimal coverage and service levels across markets
• Leverage analytics to track key performance metrics, identify trends, and implement data-backed improvements to the account management function
• Partner cross-functionally with Sales, Product, Operations, and Member Services to enhance the client experience and drive engagement
• Implement strong processes to identify risks early, address client concerns proactively, and minimize churn

What You'll Bring

• 10+ years of experience in Account Management, Client Success, or a related function, ideally within health insurance, employee benefits, or a high-growth environment
• 4+ years of experience in people management roles, with a proven track record of leading and developing teams
• Proven ability to develop and scale an Account Management function, with a strong track record of retention and relationship management
• Deep understanding of client success best practices, workforce planning, and team development
• Highly analytical mindset with experience leveraging data to inform decision-making
• Strong leadership skills with the ability to coach and elevate a team
• Excellent communication, stakeholder management, and problem-solving abilities
• Excitement for working in a fast-paced, high-growth environment
• Willingness to travel up to 30%
• Bachelor's Degree 

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.