Director of Account Management

About the Role

Sidecar Health is looking for a Director 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 role is right for someone 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. This is a rare opportunity for a senior operator who wants to leave a fingerprint on how a fast-growing company scales its most client-critical function.

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 KPI