Accounting Manager, Regulatory

Sidecar Health is transforming the health insurance industry by putting members in control of their healthcare decisions. We combine innovative technology with transparent pricing to create a better healthcare experience. As we continue to grow, we're seeking a Regulatory Accounting Manager to join our finance team and ensure excellence in our regulatory compliance and statutory reporting. 

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

About the Role

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. 

Key Responsibilities 

Statutory Accounting & Financial Reporting 

• Prepare statutory basis financial statements and related regulatory filings in accordance with NAIC Statutory Accounting Principles (SAP) and state insurance department requirements.  

• Ensure compliance with state-specific prescribed and permitted accounting practices  

• Maintain detailed understanding of both GAAP and STAT accounting frameworks and reconcile differences between the two 

• Monitor and implement changes to NAIC Accounting Practices & Procedures Manual and relevant SSAPs and assess impact on accounting treatments and reporting requirements 

Regulatory Compliance & Filings 

• Oversee preparation and submission of Medical Loss Ratio (MLR) filings and rebate calculations in compliance with ACA requirements 

• Manage Risk-Based Capital (RBC) calculations and regulatory capital adequacy reporting 

• Coordinate and respond to external audit requests, including state insurance department audits, examinations, inquiries, and information requests 

• Aid in the preparation and filing of supplemental regulatory reports including management discussion and analysis 

• Maintain current knowledge of multi-state insurance regulatory requirements 

Tax Compliance & Reporting 

• Coordinate the preparation of federal and state income tax returns with external tax advisors for all regulated entities 

• Manage quarterly tax provision calculations and ensure proper documentation 

• Support tax audits and respond to information requests from taxing authorities 

• Monitor tax law changes affecting insurance entities and assess financial impact 

Internal Controls & SOC Compliance 

• Maintain and enhance internal controls over financial reporting (ICFR) for regulatory accounting processes 

• Support SOC 1 and SOC 2 compliance activities, including control documentation and testing 

• Coordinate with Internal Audit on control assessments and remediation activities 

• Team Leadership & Development 

• Mentor and develop accounting staff on statutory accounting principles and regulatory requirements, where appropriate 

• Partner with cross-functional teams to support business development initiatives 

• Foster a culture of accountability, continuous improvement, and regulatory excellence 

• Participate in recruiting and onboarding of finance team members 

Job Qualifications:  

• Bachelor's degree in Accounting, Finance, or related field required 

• CPA certification strongly preferred (active and in good standing)

• 8+ years of progressive accounting experience in a regulated insurance entity 

• 5+ years of hands-on experience with statutory accounting principles and NAIC reporting 

• Demonstrated experience preparing and filing quarterly and annual statutory statements 

• Proven track record with MLR calculations, filings, and rebate determinations 

• Experience with state insurance department examinations and regulatory inquiries 

• Strong working knowledge of GAAP to STAT reconciliations and differences 

• Experience with insurance tax compliance including premium taxes across multiple states 

• Familiarity with SOC 1 and SOC 2 compliance frameworks 

• Master's degree in Accounting or MBA preferred 

• Public accounting experience with Big 4 or national firm preferred  

• Occasional travel may be required for regulatory examinations or industry conferences 

• Extended hours may be required during quarterly and annual filing periods 

Required Technical Skills & Knowledge: 

• Expert knowledge of NAIC Statutory Accounting Principles and the AP&P Manual 

• Strong understanding of insurance regulatory framework and state filing requirements 

• Advanced proficiency in accounting systems and financial reporting tools 

• Advanced Excel skills including complex formulas, pivot tables, and data analysis 

• Working knowledge of NetSuite or similar ERP systems preferred 

• Familiarity with investment accounting standards (ASC 320, ASC 326/CECL) preferred 

What You'll Get

• Competitive salary, bonus opportunity, and equity package  
• Comprehensive Medical, Dental, and Vision benefits
• A 401k retirement plan
• Paid vacation and company holidays
• Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S.