FacultyFaculty/Author Profile

Cynthia R. Shoss


New York, NY, USA

A nationally recognized adviser on insurance regulatory matters, Cynthia Shoss co-leads Sutherland’s Insurance Transactions & Products practice. Cynthia guides clients through transformative transactions, including demutualizations, mergers, acquisitions, conversions and other restructurings. She also assists clients with legislation, examinations and investigations and with compliance, governance and investment issues.

For more than 30 years, Cynthia has counseled clients in various sectors of the insurance industry including life insurance, property/casualty insurance, health insurance, title insurance and workers’ compensation. She works with Fortune 500 companies, state departments of insurance and attorneys general, investment bankers and multinational clients.

Cynthia joined Sutherland from Dewey & LeBoeuf where she was co-chair of the Insurance Regulatory Department, formerly Managing Partner of LeBoeuf’s London office, and chair of the firm’s pro bono practice. She also served on the firm’s Diversity Committee, as she does at Sutherland, and was a founder of the LeBoeuf Women’s Initiatives Group.


Sutherland advises Verizon on the transfer of $7.5 billion pension obligation to Prudential. Sutherland advised telecommunications giant Verizon on the insurance aspects of its $7.5 billion transfer in pension obligations to The Prudential Insurance Company of America.

Sutherland attorney represented Security Benefit in a sponsored demutualization. During the financial crisis, Security Benefit Mutual Holding Company was carefully guided through the regulatory approval process and subsequent transaction, successfully completing a sponsored demutualization by Guggenheim Partners.

Sutherland attorney represented Prudential in its demutualization and in a subsequent acquisition.

Prudential’s extraordinarily complex demutualization commenced with drafting and securing passage of enabling legislation and culminated with the second post-9/11 IPO and distribution to 10 million policyholders. Subsequently, regulatory approvals were secured for Prudential's acquisition of American Skandia Life.

Awards and Rankings

Recognized in the Guide to the World’s Leading Women in Business Law in Insurance and Reinsurance (2012-2013)

Named among “25 Women to Watch” in Insurance, Risk Management and Employee Benefits Worldwide by Business Insurance (December 2010)

Recognized in Chambers USA America’s Leading Business Lawyers in Insurance (2003- 2013)

Professional Activities

Member, Board of Overseers and Executive Committee of the School of Risk Management, Insurance and Actuarial Science of the Peter J. Tobin College of Business of St. John’s University

Former Chair, Insurance Section, former Co-Chair, Diversity Committee, and former Board member of the Association of Life Insurance Counsel (ALIC)

Vice Chair, Board of Advisors, and former Chair, Board of Directors, of Lawyers Alliance for New York

Chair, Board of Directors, Economic Mobility Corporation Member, International Insurance Society

Former Member, Board of Directors, The Compliance and Ethics Forum for Life Insurers Former Chair, Board of Directors, Power of Attorney

Former Member, Board of Directors, and former Vice President of The Risk Foundation Formerly certified by the Insurance Marketplace Standards Association (IMSA) as a Qualified Independent Assessor

Former Member, Westchester County Airport Advisory Board


Hot Topics Affecting the Insurance Industry (August 2013) Client In-house CLE Presentation

Regulatory/Receivership Modernization After Dodd-Frank: SIFIs, OLA, SMI, ORSA, and State/Federal/International Cooperation (July 2013) NOLHGA 21st Annual Legal Seminar

Insurance Investment Laws (February 26, 2013) CLE Presentation

Transactional Boot Camp (January 2013) Tulane University Law School 2nd Annual Intersession Program

Dodd-Frank Act – One Year Later (September 2012) LICONY Annual Legislative & Regulatory Conference

Risk Disclosure Regimes & Other Solvency Modernization Developments (July 2012) LICONY/NYSDFS Life Insurance Compliance Seminar

Inside an Insurance Company—Navigating the Changing Landscape—Advisors Views' About the Impacts of Regulatory Reform (July 2012) ACLI Compliance & Legal Sections Annual Meeting

Regulatory Modernization Activities Affecting Insurers—The Impact on Fraternals (2012, 2011) American Fraternal Alliance Annual Meeting (2011), Association of Fraternal Benefit Counsel Annual Meeting (2012, 2011)

Financial Services Regulatory Reform (2010) ACLI Annual Meeting

State, NAIC and Federal Responses to the Economic Crisis (2010, 2009) LICONY Annual Legislative and Regulatory Conference

Mutual and Stock Insurance Companies and Conversions from One to the Other (2008) CLE Presentation

Defining Roles and Responsibilities: Regulatory Compliance and Risk Management (2007) ACLI Annual Meeting

Compliance Developments and Emerging Issues (2006) ACLI Annual Meeting

Demutualizations, MHC Conversions and Mergers of Mutuals (2004) CLE Presentation

Closed Blocks in Demutualizations and Mutual Holding Company Conversions (1998) ALIC Annual Meeting

Alternative Structures, Regulation and Fairness to Policyholders (1998) Tokyo


  • LL.M. in Taxation, New York University School of Law
  • J.D., Tulane University Law School, Editorial Board, Tulane Law Review
  • B.A.,cum laude, Newcomb College of Tulane University

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