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Stephen R. DiCenso, FCAS, MAAA

Consulting Actuary
Windsor, CT, US

Tel: +1 860 6870160

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Professional Designations

  • Fellow, Casualty Actuarial Society
  • Member, American Academy of Actuaries


  • BA, Mathematics, Northwestern University, Phi Beta Kappa
  • Graduate, The Hartford's Business Mastery Certificate Program

Current Responsibility

Steve is a principal with the Boston office of Milliman. He joined the firm in 2008.


Steve has enjoyed a multifaceted property and casualty actuarial career, with most of his experience serving the alternative markets. With Milliman, he has focused on serving captives, large self-insured corporations, mid-sized insurers and public entity risk pools, and state regulators. This includes reserving, pricing, surplus management, cost allocation, financial examination work, due diligence, financial simulation modeling, and risk financing. He also consulted for seven years with a major accounting firm, primarily performing loss reserving for larger insurance and reinsurance companies.

His insurance company experience includes chief actuary positions at an alternative markets insurer and a third-party administrator owned by a major insurer as well as senior management experience with a property and casualty programs insurer and a fidelity and surety bond insurer. Steve has had responsibility for overseeing pricing, reserving, and planning functions, while also providing analysis on reinsurance procurement and regulatory support. He has managed staffs of up to 17 people.

Steve’s primary area of actuarial expertise is in alternative market issues and commercial line coverages, including workers’ compensation claims predictive modeling. He brings a deep understanding of claims issues from his TPA experience, where he managed benchmarking, research, and financial functions. In addition to his alternative and traditional markets expertise, he has specialized experience in excess workers’ compensation and bond lines.

Presentations and publications

  • “Workers’ Compensation Predictive Modeling for PEOs: A New Tool to Improve Business Performance,” PEO Insider, September 2014
  • “The Right Retention,” Captive Review, March 2014
  • “Under Analysis: Evaluating Retention Levels in a Hardening Market,” Best’s Review, November 2012
  • “WC Medical Costs: A Predictive Diagnosis,” VCIA (2011)
  • “Transformational Claims Initiatives: Optimizing Claims Processing Results,” IASA (2011)
  • “Seize the Moment – Healthcare Reform and Workers’ Comp,” Contingencies, Jan/Feb. 2011


  • President (2017) and Board of Directors, CT Captive Insurance Association
  • Member, CAS Financial Reporting and Analysis Committee, 2016
  • Member, CAS Task Force on Cyber Risk
  • Past chairperson and member, CAS Committee on Health Care Issues, 2008–2015
  • Past member, Self-Insurance Institute of America (SIIA) ART Committee, 2010–2012
  • Past member, CIC-DC Education Committee
  • Past member, CICA Captive Operational Best Practices Advisory Committee, 2009
  • Work at Milliman

    • “I was offered a chance to come in, shake things up, create something."
    Work at Milliman