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 looking for a Head of Account Management to build and lead the function responsible for retaining and growing our employer book of business. This is a strategic leadership role that will define how account management works at scale.

You will set the direction, build the infrastructure, and develop the talent model that allows Sidecar Health to serve increasingly large and complex employer groups — shifting from manual, reactive support to scalable, systematic account management.

This is an exciting opportunity for senior operator who who can hold two things at once: genuine energy for client-facing work with brokers and HR leaders, and the strategic mind to build the systems, structure, and playbooks that make great account management repeatable.

What You'll Own:

Strategic Leadership

• Define the vision and operating model for Account Management across mid-market employer groups (up to 10,000 employees), including both fully insured (GFI) and self-insured accounts
• Create the strategic roadmap for transitioning the team from manual, high-touch processes to scalable, automated systems — without sacrificing client experience
• Identify where human-led account management adds the most value and design the infrastructure around it
• Partner with C-levels to align account management strategy with company growth targets and new market expansion

Building & Scaling the Function

• Architect the organizational structure, hiring plan, and role definitions needed to support a growing and more complex book of business
• Build and own the tools, playbooks, and processes that enable account managers to serve larger groups efficiently
• Drive automation and self-service capabilities in partnership with product, operations, and technology teams
• Develop clear escalation paths and operational infrastructure so account managers can stay focused on client development rather than issue resolution

Client & Broker Relationships

• Serve as a senior client-facing leader - present with key broker partners and HR decision-makers on high-stakes accounts
• Model and reinforce a culture of proactive, consultative account management throughout the team
• Travel approximately once per month for key client meetings and broker events

Performance & Accountability

• Own retention, growth, and satisfaction targets across the mid-market book
• Define and track KPIs that reflect both client health and team effectiveness
• Report to senior leadership on performance, risk, and strategic priorities

What You'll Bring

• 10+ years of experience in Account Management, Customer Success, or Client Strategy within the health insurance or benefits industry, with 5+ years in a senior leadership role
• Deep knowledge of employer group health insurance
• Experience building and scaling account management functions and infrastructure
• A track record of leading and driving outcomes through organizational design
• Systems-level thinker: you identify structural gaps and build durable solutions, rather than patching issues as they arise
• Natural energy for client-facing work — you are genuinely energized by broker and employer relationships and bring that energy into how you lead
• Strong executive presence and communication skills, with the ability to influence internal stakeholders and senior client contacts alike
• Comfort operating in a fast-moving, high-growth environment where ambiguity is the norm and resourcefulness is essential
• Bachelor's degree required
• Must reside in Florida, Georgia, Ohio, or Texas for consideration

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.