Sykes, Benjamin P.

Benjamin P. Sykes




Benjamin P. Sykes has over a decade of experience in the insurance and reinsurance industry advising public and private companies in a wide range of corporate, transactional and regulatory matters.

His practice spans across all major lines of insurance (life, P&C and health) and includes insurance M&A, joint ventures, corporate governance, licensing of insurers and agencies, investment compliance, insurance holding company act issues, organizing alternative risk transfer vehicles such as captive insurance companies, risk retention and purchasing groups, financial examinations, producer compensation and advising InsurTech startups and other emerging growth companies.

Representative Experience

Mergers & Acquisitions

Ben has worked on numerous insurance M&A transactions involving the acquisition or sale of both insurers and producers, as well as related transfers of books of business. These deals have included negotiating stock purchase agreements, merger agreements, transfers of renewal rights, loss portfolio transfers agreements and bulk reinsurance transactions. In addition to drafting the deal the documents, his work includes identification of regulatory risk through due diligence, drafting related ancillary services agreements and assisting clients in obtaining necessary regulatory approvals. Ben has also acted as special regulatory counsel for clients, including many private equity firms.

Representative mergers & acquisition experience includes:

  • Counseled Property Casualty Insurers Association of America (PCI) on its merger with American Insurance Association (AIA) to form American Property Casualty Insurance Association (APCI)
  • Led Guardian Life’s sale 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


Ben has advised numerous InsurTech startups on everything from formation, to licensure, to general insurance compliance and product development. He is the author of the Insurance Industry Primer for InsurTechs, used by InsurTechs across the nation to educate themselves and new hires on insurance regulation and related issues. Ben also advises incumbent carriers and producers on investment in and partnerships with InsurTechs.

Representative InsurTech experience includes:

  • Advised vehicle service contract provider on contract creation and regulatory matters
  • Counseled 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 on rebating restrictions and anti-inducement laws

Payor-Provider Risk Transfer Matters

Ben has advised on health care transactions including formation and acquisition of health insurers, joint ventures, integrated delivery systems, risk-assuming provider networks, hospital-physician ventures and compliance. He has particular experience in the application of insurance laws related to providers assuming insurance risk and forming or partnering with insurers.

Representative payor-provider experience includes:

  • 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


A substantial portion of Ben’s practice is focused on negotiating reinsurance agreements across all lines of insurance and advising clients on credit for reinsurance issues. In the health space, Ben has negotiated complex quota share reinsurance agreements between hospital and payor joint venture partners. In the property and casualty space, Ben has experience negotiating loss portfolio transactions (LPT), adverse development cover (ADC), fronting arrangements, and other unique and bespoke transactions. In the life space, Ben has worked on XXX reserve financing transactions, as well as novations and commutations of existing reinsurance. 

Representative reinsurance experience includes:

  • Negotiated off-shore reinsurer’s approximately half billion dollar LPT and ADC
  • Drafted health plan’s quota-share reinsurance agreement with hospital systems captive
  • Led negotiation of a reinsurance and administrative services agreement for ancillary health benefit administrator with a fronting carrier

Service Contracts

Ben works extensively with administrators and providers of service contract and ancillary product offerings, including on issues of formation, contract drafting, national licensure and reinsurance matters. In addition, Ben often serves as special regulatory counsel to his private equity clients during their acquisitions in this space.

Representative service contract and ancillary product experience includes:

  • Counsel to major auto manufacturer on various vehicles service contract (VSC) matters
  • Counsel to private equity fund in its acquisition of VSC administrator
  • Advised major retailer on regulatory issues associated with service contracts and extended warranties for electronic devices

Professional History

  • Associate, Locke Lord LLP
  • Associate, Foley & Lardner LLP