Benjamin P. Sykes

Ben’s practice covers all major lines of insurance, including life, property and casualty, and health. He assists clients with insurance mergers and acquisitions, joint ventures, corporate governance, licensing, investment compliance, and insurance holding company act issues. Ben also has experience organizing alternative risk transfer vehicles, such as captive insurance companies, and advising insurtech startups and emerging growth companies.

Ben’s clients range from established insurers and producers to private equity firms and innovative insurtech startups. He helps them navigate complex transactions, regulatory compliance, and strategic partnerships.

Mergers and Acquisitions

• Work on numerous insurance M&A transactions involving the acquisition or sale of insurers and producers, as well as related transfers of books of business. These deals include negotiating stock purchase agreements, merger agreements, transfers of renewal rights, loss portfolio transfers agreements, and bulk reinsurance transactions. In addition to drafting the deal documents, his work includes identification of regulatory risk through due diligence, drafting related ancillary services agreements, and assisting clients in obtaining necessary regulatory approvals. Act as special regulatory counsel for clients, including many private equity firms.
• Counseled PCI on its merger with American Insurance Association (AIA) to form the American Property Casualty Insurance Association (APCI).
• Led Guardian Life’s divestiture of its 401k business to Ameritas.
• Advised COUNTRY Financials sale of MiddleOak Insurance Group’s personal lines to MAPFRE.
• Represented Welborn Health Plans in its exit of the commercial group health market and related endorsement of Anthem.

Insurtech

• Advise numerous insurtech startups on formation, licensure, general insurance compliance, and product development. Author of “Insurance Industry Primer for InsurTechs,” used by insurtechs across the nation to educate themselves and new hires on insurance regulation and related issues. Advise incumbent carriers and producers on investment in and partnerships with insurtechs.
• Advised a vehicle service contract provider on contract creation and regulatory matters.
• Counseled a niche-market web-based managing general agent on disclosure compliance, electronic delivery, and general corporate matters.
• Provided testimony on behalf of the insurtech community to the National Association of Insurance Commissioners (NAIC)’s Innovation and Technology Task Force on rebating restrictions and anti-inducement laws.

Payor-Provider Risk Transfer Matters

• Advise on health care transactions, including the formation and acquisition of health insurers, joint ventures, integrated delivery systems, risk-assuming provider networks, hospital-physician ventures, and compliance. He has experience in the application of insurance laws related to providers assuming insurance risk and forming or partnering with insurers.
• Counsel to Aetna Inc. in its insurance joint venture with Texas Health Resources.
• Counsel to Aetna Inc. in its insurance joint venture with Allina Health System.
• Counsel to St. Luke’s University Health Network in its collaboration with Geisinger Health System.

Reinsurance

• Negotiate reinsurance agreements across all lines of insurance and advise clients on credit for reinsurance issues.
• Negotiate complex quota share reinsurance agreements between hospital and payor joint venture partners.
• Negotiate loss portfolio transactions (LPT), adverse development cover (ADC), fronting arrangements, and other unique and bespoke transactions.
• Work on reserve financing transactions as well as novations and commutations of existing reinsurance.
• Negotiated an offshore reinsurer’s half-billion-dollar LPT and ADC.
• Drafted a health plan’s quota-share reinsurance agreement with a hospital system’s captive.
• Led the negotiation of a reinsurance and administrative services agreement for an ancillary health benefit administrator with a fronting carrier.

Service Contracts

• Work extensively with administrators and providers of service contract and ancillary product offerings, including on issues of formation, contract drafting, national licensure, and reinsurance matters.
• Often serve as special regulatory counsel to private equity clients during their acquisitions in this space.
• Counsel to major auto manufacturer on various vehicles service contract (VSC) matters.
• Counsel to a private equity fund in its acquisition of a VSC administrator.
• Advised a major retailer on regulatory issues associated with service contracts and extended warranties for electronic devices.

• Thomson Reuters Stand-out Lawyer – independently rated lawyers (2023-2025)
• Best Lawyers in America®: Health Care Law (2023-2026)