Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and accessible for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen.

The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent.

If you want to use your talents to transform healthcare in the United States, come join us!

About the Role

The Senior Accountant position will sit on the financial reporting side of our finance organization and act as the accounting support bridge between Finance Operations and Financial Reporting. This role exists to own the back-end accounting, reconciliations, and controls for a defined set of areas to enable sufficient controls and segregation of duties in the outlined areas.  As Sidecar Health scales rapidly, this role will also help modernize processes, including leveraging AI and automation tools, to keep pace with increasing transaction volume and complexity.

This is an ownership role. You will be the single point of accountability for the financial statement accounts and reconciliations assigned to you — preparing entries where appropriate, reconciling accounts in full each period, investigating variances, and partnering with Finance Operations and FP&A as the financial reporting liaison for all administrative costs of the business.

Key Responsibilities

Administrative and operating expense accounting

• Prepare and record administrative and operating expense accruals (e.g., audit, tax, and other recurring professional-services accruals)
• Own a portfolio of prepaid and accrual reconciliations
• Reconcile payroll and benefit-related accounts each period, providing an independent review layer on entries booked by the payroll processor
• Serve as a backup for the processing of payroll and related benefits

Investment and debt accounting

• Maintain investment accounting entries and reconciliations across the parent, insurance entities, working within established review controls
• Maintain debt accounting, assessing and implementing any technical accounting requirements resulting from changes in terms or rates
• Prepare covenant compliance and other monthly reporting requirements for lenders

Reconciliations, close, and controls

• Serve as preparer and/or independent reviewer to support segregation of duties across the close for assigned areas, within close and reconciliation deadlines
• Support software capitalization / internal-use software accounting and related documentation
• Support lease accounting under ASC 842 and other technical accounting topics related to the company's administrative expenses

Handoffs and cross-team partnership

• Absorb recurring one-off tasks that don't have a natural home, freeing finance operations staff to concentrate on scaling their core work to meet the demands of our growing business
• Investigate variances and partner with Finance Operations and FP&A to resolve issues at the source
• Partner with FP&A to create system-driven allocations of administrative expenses across cost centers
• Identify and help implement AI-enabled or automation tools to improve the efficiency and scalability of accounting processes as transaction volume and complexity grow

Required Qualifications

• Bachelor's degree in accounting or finance
• 3–5 years of progressive accounting experience
• Hands-on experience owning account reconciliations and month-end close
• Strong understanding of accrual accounting and internal controls / segregation of duties
• Detail-oriented and accountable, with the ability to take full ownership of an area and drive it to completion
• Comfortable working across teams and communicating clearly between operational and reporting functions

Preferred Qualifications

• CPA (or active candidate) — a plus, not required
• Public accounting / Big Four experience — a plus, not required
• Experience in a highly-regulated industry (e.g., insurance, healthcare, financial services), including statutory and/or GAAP reporting and familiarity with multi-entity structures
• Experience with NetSuite and a close-management platform such as FloQast

This role is scoped as a senior individual-contributor position with room to grow toward a management track over time. It is a strong fit for someone stepping up from a staff role or transitioning out of public accounting who wants ownership and progression.

Why Join Us?

• Competitive salary, bonus opportunity, and equity package
• 401(k) retirement plan with company match
• Paid vacation and company holidays
• Opportunity to make a direct impact on member experience and employee success
• The opportunity to make a meaningful impact at a rapidly growing, mission-driven company transforming healthcare in the U.S.