FORTY Under 40: Meet the judges
Captive International acknowledges the work of the stellar panel of judges who picked our finalists.
Dan Towle, CICA president
As president of the Captive Insurance Companies Association (CICA), Dan Towle combines his captive insurance industry knowledge, relationship building and leadership experience to deliver value for CICA members, advocate for the industry and foster captive utilisation. He is a frequent presenter at conferences throughout the US and internationally. He is highly visible in international media and viewed as an authority on captive insurance. He has been recognised for his contributions to the global captive insurance industry.
Towle serves on the board of directors for the International Center for Captive Insurance Education. He is a past advisory board member for World Captive Forum and chaired the Risk and Insurance Management Society exhibitor advisory committee.
Prior to CICA, he worked as the director of financial services for the state of Vermont for 17 years. There he was the chief marketing and business development professional for the state’s captive insurance industry and instrumental in its growth. More than 500 captive insurance companies were licensed during his tenure.
Anne Marie Towle, CEO - Global Risk & Captive Solutions, Hylant
A veteran of the captive insurance industry, Anne Marie Towle leads the global captive solutions team at Hylant.
She has 30 years of experience with diverse projects and has worked with captives and other alternative risk transfer vehicles in many key onshore and offshore domiciles. She manages captive projects through feasibility and implementation, developing unique customised structures tailored to each client’s needs. She has been instrumental in arranging fronting and reinsurance programmes for her captive clients.
Prior to joining Hylant, Towle was an executive vice president with JLT, and a senior consultant with Willis Towers Watson for more than seven years. She also spent time as a senior manager in public accounting and 10 years in taxation, where she provided consultancy services to captive owners. She managed client projects through feasibility and implementation processes in structuring captives and managed their accounting and tax compliance functions.
Before that, she worked in private industry in the insurance tax departments of several Fortune 500 insurance and financial sector companies.
Throughout her career, Towle has been closely involved in captive insurance organisations at the local, state and national level. She serves on the board of directors for the Vermont Captive Insurance Association (VCIA) and the International Center for Captive Insurance Education (ICCIE); the ICCIE curriculum committee and an instructor for ICCIE courses; chair of ICCIE and the conference committees of the VCIA (2017 chair), Captive Insurance Companies Association, World Captive Forum, the South Carolina Captive Insurance Association and Hawaii Captive Insurance Council.
Grainne Richmond, EVP, head of captives, Aon
Grainne Richmond joined Aon Insurance Managers (Bermuda) in September 2022 as executive vice president, head of captives. Prior to joining Aon, she was vice president of Strategic Risk Solutions (Bermuda) (SRS) (formerly Dyna Management Services).
Richmond is a qualified CPA (FCA Ireland) and has more than 21 years of captives experience in Bermuda and Cayman, having held senior roles at SRS, Artex Risk Solutions, and International Advisory Services.
Prior to captive management Richmond worked with PricewaterhouseCoopers, Dublin in the business advisory division on a variety of international and Irish companies.
Richmond is heavily involved in the Bermuda industry. She is president of the Bermuda Insurance Management Association and works closely with industry peers in discussions with the Bermuda Monetary Authority, Registrar of Companies, and the Bermuda government.
Phillip Giles, chief growth officer, accident & health, Skyward Specialty Insurance
Phillip C. Giles has more than 30 years of accident and health and property and casualty alternative risk experience and has been chief growth officer for Skyward Specialty since July 2024.
Giles was named Cayman Reinsurance Specialist of the Year by Captive International magazine in 2019 and again in 2021. He holds a bachelor’s degree from Western Illinois University, as well as the Certified Employee Benefit Specialist professional designation from the International Foundation of Employee Benefit Plans and the Wharton School of the University of Pennsylvania.
Giles has achieved fellowship status with the International Foundation of Certified Employee Benefit Specialists.
Michael Meehan, principal, Milliman
Mike Meehan is a principal with Milliman and has more than 25 years of experience working with captive insurance companies and other alternative risk financing programmes.
Meehan is an active participant in the captives industry and a frequent speaker and author on captives and alternative risk financing. He is a board member of the North Carolina Captive Insurance Association and an active member on numerous committees for captive domicile and other associations.
Meehan is also a former board member and treasurer of the Vermont Captive Insurance Association (VCIA). He also won VCIA’s 2021 industry service award.
Anjanette Fowler, managing director, PNC Investment Asset Management
Anjanette Fowler is managing director of PNC Institutional Asset Management, a member of its insurance solutions group focused solely on providing investment and banking solutions for the captive, self-insuring and traditional commercial markets.
She coordinates the development and delivery of strategic investment programmes, supports client relationship needs and participates in client and industry education. As a former portfolio manager, Fowler brings almost 30 years of insurance company focused investment management experience, along with a valuable understanding of the financial complexities unique to the insurance industry.
She is a frequent speaker at risk management conferences, including CICA, MPL, NAMIC, NRRA, VCIA, AZCIA, NCCIA and WRCIC. Fowler is the acting chair of the Captive Insurance Companies Association’s amplify women committee, and for the past number of years has been recognised as one of the captive insurance industry’s most influential professionals in the Annual Power 50 list.
Sandy Bigglestone, acting commissioner, Vermont Department of Financial Regulation
Sandy Bigglestone is acting commissioner of the Vermont Department of Financial Regulation. She is responsible for the administration and regulation of captive insurance companies and risk retention groups. She was previously deputy commissioner of the Captive Insurance Division at the Vermont Department of Financial Regulation.
Having been with the division since 1997, Bigglestone had 25 years of experience regulating captive insurance before being appointed deputy commissioner effective September 1, 2022, after serving as a principal staff member to her predecessor for 14 years.
Bigglestone is a certified public accountant, certified financial examiner, certified public manager with the State of Vermont and earned an associate professional in insurance regulation designation from the National Association of Insurance Commissioners.
In 2018, Bigglestone was a recipient of the Women to Watch Award presented by Business Insurance for her leadership, expertise and accomplishments in the captive insurance industry.
Gary Osborne, vice president, Risk Partners
Gary Osborne joined Risk Partners as vice president of alternative risk programmes in 2018. Osborne has 37 years of captive insurance experience, having worked in four different domiciles (Bermuda, Vermont, Hawaii and South Carolina). He has been involved in writing parts of the captive laws in South Carolina and Tennessee and also a faculty member of International Center for Captive Insurance Education.
Osborne’s career began in 1982 on the audit staff of Deloitte Haskins and Sells, followed by senior auditing role at PwC. He then enjoyed progressive responsibilities while managing captive portfolios at Marsh & McLennan (Bermuda) then Johnson & Higgins (Vermont). Sedgwick then hired Osborne to establish a captive management operation in Hawaii. After Sedgwick outsourced captive management to USA Risk Group 1995, he held various management positions there, including president from 1995 to 2018. Osborne was responsible for all aspects of company operation, including expanding the company through acquisitions, overseeing captive management and financial operations.
Osborne has often been featured in captive and other industry publications. He has been very active in industry trade associations, including Hawaii Captive Insurance Council (conference chair and treasurer), National Risk Retention Association (director and currently government affairs committee), Tennessee Captive Insurance Association (director), South Carolina Captive Association (current chairman), and a member of the CICA task group for publication of captive insurance standards for service providers.
Osborne has also been recognised by the Tennessee Captive Insurance Association as the Jim Hinton volunteer of the year and by the Vermont Captive Insurance Association with its industry service award.
Lesley Thompson, managing director, Cayman Islands, WTW
Lesley Thompson is the managing director of the Cayman Islands office of WTW. She is a captive insurance professional with more than 25 years’ experience in accounting, insurance and structured finance.
As part of WTW’s operations since March 2020, she has extensive knowledge of forming all kinds of captives. Thompson also gives back to the industry and is a past chair of the International Managers Association of Cayman and a lecturer for ICCIE for nine years.
Nicholas J. Hentges, chief executive, Captive Resources
Nick Hentges, chief executive of Captive Resources, has an extensive background with insurance company, brokerage and captive consulting and management operations. Early in his career he held several management positions in underwriting and marketing with CIGNA. In 1989, he moved to Kirke-Van Orsdel, a large regional broker that specialised in association programmes, to develop its property and casualty book of business.
In 1993 Hentges joined Captive Resources to develop and manage one heterogeneous and two homogeneous group member-owned captives. He spent 14 years as the business development manager, working with captive executives to build new captives and grow existing captives. He is a member of the management team that acquired the assets of Captive Resources and sister company Kensington Management Group in the Cayman Islands from its publicly held parent company in 2002.
Hentges has used his 26 years of captive experience to help educate corporations on the benefits of pooling their resources and lowering their insurance costs through the formation of member-owned group captive insurance companies. In his present role he has oversight of and responsibility for business development, administration, finance, claims and risk control, travel and human resources, and focuses on the company’s long-term strategic plans.
Nate Reznicek, president and principal consultant, Captives.Insure
Nate Reznicek, president and principal consultant of Captives.Insure, heads an award-winning global captive insurance consulting and underwriting firm headquartered in Tennessee.
Reznicek maintains an active leadership position in the captives industry and has served on the Captive Insurance Companies Association (CICA) programming committee, The Self Insurance Institute of America’s (SIIA) captive advocacy and captive committees, as well as the International Center for Captive Insurance Education (ICCIE) board of directors, curriculum committee and faculty. The recipient of multiple awards and industry recognition by Risk & Insurance Magazine, Business Insurance, US Captive Services Awards, Captive International and Captive Review, he serves as a subject matter expert on captive insurance for brokers and advisers across the country. A native of Wichita, Kansas, Reznicek spent his formative years at the University of Kansas, as an airman in the USAF Air National Guard.
Michelle Sivanayson, managing director, Marsh Captive Solutions region leader – Islands
As leader of the Islands region captive practice, Sivanayson is responsible for the overall client service, operational strategy and management of the Bermuda, Cayman Islands and Barbados offices within the captive solutions practice. She establishes growth and retention strategies, ensures success of the client experience, trains and mentors and oversees performance management for colleagues for the region as a whole. In addition, she serves on the Marsh Captive Solutions global executive team.
Sivanayson joined Marsh Captive Solutions in May 2004, originally in the Bermuda office as an account manager where she managed a portfolio of captive clients overseeing their day-to-day operations.
After three years, she moved to Marsh Canada and joined the captive operations group in Halifax, where she spent the next 16 years in various roles. During this time, she became the global operations leader for captives, leading and overseeing both the Halifax and Mumbai operations’ teams. In this role Sivanayson led a team of more than 150 colleagues fostering a positive and collaborative work environment by setting direction and empowering colleagues actively to work towards Marsh Captive’s goals, overseeing global initiatives and data driven decisions that elevate the operational performance of the practice.
Prior to joining Marsh, Sivanayson worked in a Toronto-based company as a financial controller. She was responsible for financial reporting, HR, budgeting, pricing and the overall day-to-day company management.
Click here to read Captive International’s third FORTY Under 40 2025 publication.
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