[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.ResponsibilitiesDefine 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 accountsCreate the strategic roadmap for transitioning the team from manual, high-touch processes to scalable, automated systems — without sacrificing client experienceIdentify where human-led account management adds the most value and design the infrastructure around itPartner with C-levels to align account management strategy with company growth targets and new market expansionArchitect the organizational structure, hiring plan, and role definitions needed to support a growing and more complex book of businessBuild and own the tools, playbooks, and processes that enable account managers to serve larger groups efficientlyDrive automation and self-service capabilities in partnership with product, operations, and technology teamsDevelop clear escalation paths and operational infrastructure so account managers can stay focused on client development rather than issue resolutionServe as a senior client-facing leader - present with key broker partners and HR decision-makers on high-stakes accountsModel and reinforce a culture of proactive, consultative account management throughout the teamTravel approximately once per month for key client meetings and broker eventsOwn retention, growth, and satisfaction targets across the mid-market bookDefine and track KPIs that reflect both client health and team effectivenessReport to senior leadership on performance, risk, and strategic prioritiesSkills10+ 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 roleDeep knowledge of employer group health insuranceExperience building and scaling account management functions and infrastructureA track record of leading and driving outcomes through organizational designSystems-level thinker: you identify structural gaps and build durable solutions, rather than patching issues as they ariseNatural energy for client-facing work — you are genuinely energized by broker and employer relationships and bring that energy into how you leadStrong executive presence and communication skills, with the ability to influence internal stakeholders and senior client contacts alikeComfort operating in a fast-moving, high-growth environment where ambiguity is the norm and resourcefulness is essentialBachelor's degree requiredBenefitsCompetitive salary, bonus opportunity, and equity packageComprehensive Medical, Dental, and Vision benefitsA 401k retirement planPaid vacation and company holidaysOpportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S.Company OverviewSidecar Health's employer plans empower members with transparency, control, and financial incentives to make smart healthcare decisions. It was founded in 2018, and is headquartered in Covina, California, USA, with a workforce of 201-500 employees. Its website is https://sidecarhealth.com.