Sidecar Health

Bookkeeper

• Process accurate and timely payroll for multiple entities across salary, hourly, and commission-based employees
• Manage end-to-end payroll operations including data entry, calculations, deductions, and comprehensive reporting
• Ensure compliance with federal, state, and local payroll regulations across all entities
• Reconcile payroll accounts, resolve discrepancies, and maintain meticulous financial accuracy
• Prepare and review bi-monthly payroll inputs such as salary adjustments, payroll taxes, deductions, garnishments, and new hires
• Collaborate with HR, Finance, and other departments to ensure seamless payroll operations and cross-functional alignment
• Maintain and optimize payroll systems and processes for efficiency, accuracy, and scalability
• Maintain compensation records, payroll files, and related documentation for all employees
• Manage census reporting and support month-end and year-end payroll activities including tax filings, audits, and compliance reporting
• Record and audit accrued annual leave, sick leave, and other leave balances
• Handle employee payroll inquiries with exceptional internal customer service and problem-solving
• Prepare detailed payroll reports and analytics for management decision-making
• Support month-end and year-end payroll activities including tax filings, compliance reporting, and audit preparedness
• Build scalable payroll infrastructure and documentation to support our high-growth environment

Payroll Manager

Accounting Manager

• The Regulatory Accounting Manager will be responsible for managing all aspects of statutory accounting, regulatory reporting, and compliance for Sidecar Health Insurance Company and related entities.
• This role serves as the subject matter expert on insurance regulatory accounting requirements, working closely with cross-functional teams to ensure accurate and timely filings with state insurance departments and federal agencies.
• Reporting to the Director, Financial Accounting and Reporting, this position plays a critical role in maintaining the company's regulatory standing and supporting strategic business initiatives.

Regulatory Accounting Manager

Customer Support

• Visit our clients onsite across Ohio and support members in navigating their Sidecar Health plans
• Act as in-person support for client groups and members after enrollment and during other periods of escalated necessity
• Assist our Account Management team in identifying and establishing positive relationships with key individuals and HR departments at the client groups they work with
• Work in a traditional member care capacity, answering calls, responding to web chats and/or responding to emails
• Provide excellent customer service in a timely and positive manner
• Build rapport and maintain positive relationships with existing members to understand their needs and ensure a memorable member experience

Field Support Representative, Customer Support

• Visit clients onsite across Ohio and support members in navigating their Sidecar Health plans
• Work in the field supporting members at their worksites and partner closely with Account Management, Claims, and Provider teams to assist group members
• Act as in-person support for client groups and members after enrollment and during periods of escalated necessity
• Assist Account Management in identifying and establishing positive relationships with key individuals and HR departments at client groups
• Work in a traditional member care capacity: answering calls, responding to web chats, and responding to emails
• Provide excellent customer service in a timely and positive manner
• Build rapport and maintain positive relationships with existing members to understand their needs and ensure a memorable member experience

Field Support Representative, Customer Service

Actuary

• Lead Sidecar Health\'s actuarial pricing, reserving, and forecasting engine and manage a small team of senior actuarial analysts
• Own pricing & reserving across products: set assumptions, methods, guardrails; run experience studies and trend analyses
• Lead forecasting & capital views with Finance/FP&A; translate drivers into executive and board narratives
• Manage and develop senior actuarial analysts: work review, coaching, prioritization
• Build and scale models/tools (Excel + SQL/Python/R or actuarial platforms) with version control, documentation, and testing
• Support regulatory work: rate filings, actuarial memoranda, and audit support; coordinate with external actuaries
• Provide decision support: evaluate product changes, pricing actions, benefit design, and cost initiatives with scenario planning and sensitivity testing
• Partner with Data/Engineering to improve data quality, automation, and reproducibility
• Improve operating cadence: shorter reporting cycles, clear variance attribution, and consolidated dashboards

Director, Actuarial Pricing

Analyst

• Coordinate and maintain all prospective payment system (PPS) configuration and/or external system pricer/grouper upgrades
• Troubleshoot coding/grouping issues to determine appropriate assignment of DRG/APC
• Serve as subject matter expert related to CMS pricing rules and methodologies (MS-DRG, CMG, ASC PPS, IPF PPS, IRF PPS, Professional claims)
• Partner with training and documentation teams to build training, policy and procedure documentation related to external pricers/groupers and exception handling
• Perform root cause analysis on claim and system issues
• Partner with actuarial team on internal pricing methodology and updates
• Support claims production teams with process questions and specific claim investigations
• Implement and maintain accurate and timely critical information on claims databases
• Remain current on CMS pricing rules, regulations, coding updates, changes, and issues
• Interpret state and/or federal benefits, contracts, and business requirements and convert these terms to configuration parameters
• Code, update, and maintain provider contracts, fee schedules, and various system tables through the user interface and PPS systems

Configuration Analyst

• Handle inbound calls and chat boxes from our members in regard to Sidecar Health’s products and services
• Provide excellent customer service in a timely and positive manner
• Build rapport and maintain positive relationships with existing members to understand their needs and ensure a memorable member experience
• Handle issues and complaints where appropriate
• Maintain policies and standard operation procedures
• Help members answer questions, solve problems, and ensure access to care; collaborate within a dynamic startup team

Customer Service Representative, Member Care

Underwriter

• Lead Sidecar Health’s group underwriting function as a player-coach, personally underwriting large and complex group cases while managing the underwriting team
• Manage, mentor, and develop a team of group underwriters and oversee day-to-day operations
• Establish and maintain underwriting guidelines, policies, and processes balancing competitiveness, risk, and profitability
• Partner with Sales and Client Success to support new business opportunities, renewals, and finalist presentations
• Provide creative underwriting solutions to win new accounts while protecting financial performance
• Collaborate with Actuarial, Product, Finance, and Client Success to inform pricing strategies, renewals, and long-term client value
• Review and approve escalated underwriting decisions to ensure alignment with strategy
• Monitor underwriting performance and portfolio results, identifying trends and implementing corrective actions
• Build and maintain relationships with brokers, consultants, and reinsurers to support growth and reinsurance strategies
• Promote a culture of accountability, collaboration, and continuous improvement
• Report to the VP of Actuarial & Underwriting

Director of Underwriting

Sales

• Own the full sales cycle for ASO/NASA prospects, from pipeline generation through contract execution; Cultivate and expand strategic relationships with national benefits consultants, brokers, and employer decision-makers; Drive consultative sales conversations, clearly articulating Sidecar Health’s differentiated value proposition and ROI for self-funded employers; Partner with actuarial, underwriting, product, and implementation teams to develop compelling solutions tailored to prospect needs; Deliver presentations, finalist meetings, and executive-level pitches with credibility and executive presence; Negotiate deal structures, pricing, and contracts in collaboration with leadership and legal; Consistently meet and exceed new business sales goals and revenue targets; Maintain accurate pipeline management and reporting through CRM and sales tools; Represent Sidecar Health at industry conferences, events, and networking forums to elevate brand presence and drive business development; Partner closely with the Market President, NASA, to shape go-to-market strategies and refine sales playbooks for the ASO segment