This is for an insurance accounting pro who can own statutory reporting end to end and keep regulators happy without breaking a sweat. If you speak NAIC SAP fluently, know how to reconcile GAAP to STAT, and can run filings like clockwork, Sidecar Health is basically asking for you by name.
About Sidecar Health
Sidecar Health is transforming health insurance by putting members in control, using technology and transparent pricing to create a better healthcare experience. This role sits in Finance and helps protect the company’s regulatory standing as they scale.
Schedule
Remote, full-time. Occasional travel may be required for regulatory exams or conferences. Extended hours may be needed during quarterly and annual filing cycles. Application asks if you’re located in: CA, CT, FL, GA, MA, NC, NH, NJ, NY, OH, TX, UT, WA, or WI.
What You’ll Do
⦁ Prepare statutory financial statements and filings aligned with NAIC SAP and state requirements
⦁ Ensure compliance with state-specific prescribed and permitted practices
⦁ Maintain GAAP and STAT expertise and reconcile differences between the two
⦁ Monitor NAIC AP&P Manual and SSAP updates and assess reporting impacts
⦁ Oversee ACA Medical Loss Ratio (MLR) filings and rebate calculations
⦁ Manage Risk-Based Capital (RBC) calculations and capital adequacy reporting
⦁ Coordinate responses for state DOI audits, examinations, and regulatory inquiries
⦁ Support supplemental regulatory reporting and related documentation
⦁ Coordinate federal/state income tax returns with external advisors and manage quarterly tax provisions
⦁ Support tax audits and monitor tax law changes affecting insurance entities
⦁ Maintain internal controls over regulatory accounting and support SOC 1/SOC 2 compliance work
⦁ Mentor/develop accounting staff and support recruiting/onboarding as needed
What You Need
⦁ Bachelor’s degree in Accounting/Finance (Master’s or MBA preferred)
⦁ CPA strongly preferred (active and in good standing)
⦁ 8+ years progressive accounting experience in a regulated insurance entity
⦁ 5+ years hands-on statutory accounting + NAIC reporting experience
⦁ Experience filing quarterly and annual statutory statements
⦁ Proven MLR calculations/filings/rebates experience
⦁ Experience handling DOI examinations and regulatory inquiries
⦁ Strong GAAP-to-STAT reconciliation knowledge
⦁ Insurance tax compliance experience (including multi-state premium taxes preferred)
⦁ Familiarity with SOC 1 and SOC 2 compliance frameworks
⦁ Advanced Excel skills (pivots, complex formulas, analysis)
⦁ Preferred: NetSuite (or similar ERP), investment accounting knowledge (ASC 320, ASC 326/CECL)
Benefits
⦁ Competitive salary, bonus opportunity, and equity
⦁ Medical, dental, vision
⦁ 401(k)
⦁ Paid vacation and company holidays
Backbone note: this one is very niche. If you don’t have direct NAIC SAP + STAT statement filing experience, it’s going to be a tough sell. If you do, your application should lead with specific filings (quarterly/annual), RBC/MLR exposure, states you’ve filed in, and any DOI exam experience.
Happy Hunting,
~Two Chicks…