Senior Director of Account Management

About the role

The Senior Director of Account Management at Sidecar Health is responsible for building and leading the function responsible for retaining and growing the company's employer book of business. This role involves defining the vision and operating model for account management, setting strategic roadmaps for transition from manual to scalable processes, and aligning account management strategy with company growth targets and new market expansion.

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

Requirements

• 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
• Systems-level thinker: identifies structural gaps and builds durable solutions, rather than patching issues as they arise
• Natural energy for client-facing work — genuinely energized by broker and employer relationships and brings 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

Qualifications

• Bachelor's degree required