[Remote] Senior Director of Account Management

Note: The job is a remote job and is open to candidates in USA. Sidecar Health is redefining health insurance with a mission to make excellent healthcare affordable and accessible for everyone. They are seeking a Senior Director of Account Management to lead the function responsible for retaining and growing their employer book of business, focusing on building scalable systems and enhancing client relationships.

Responsibilities

• 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
• 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
• 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
• 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

Skills

• 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

Benefits

• 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.

Company Overview