FORTY Under 40: Meet the judges

Captive Review acknowledges the work of the stellar panel of judges who picked our finalists.

Daniel D. Towle, president, CICA

Towle has been president of the Captive Insurance Companies Association (CICA) since 2017. CICA is the only domicile-neutral trade association for the captive insurance industry. It hosts an international conference annually in the US and biennially in Europe and currently has nearly 700 members, made up of many of the most prominent captive owners and leading service providers for the industry.

Towle is a frequent presenter at conferences throughout the U.S. 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 and was voted #5 in the 2025 Captive Review Magazine Power 50, which recognises the most influential individuals in the global captive insurance industry and has been on the list annually since 2016. He was also selected as one of the 25 most influential individuals over the past 25 years in Captive Review Magazine’s “25 at 25” also published in 2024.

Previously, he worked as the director of financial services for the state of Vermont for 17 years. There he was also the chief marketing and business development director for the state’s captive insurance industry and instrumental in its growth. During his tenure more than 500 captive insurance companies were licensed in Vermont. He has 30 years of leadership and experience in the captive insurance industry.

He currently serves on the board of directors for the International Center for Captive Insurance Education. He previously has served as an Advisory Board Member for World Captive Forum, Chaired the Risk and Insurance Management Society exhibitor advisory committee and was active in various capacities with the Vermont Captive Insurance Association.

Renea Louie, chief executive, Sotera Global Management

Louie is an accomplished business professional and prominent figure in the alternative risk transfer and captive insurance industry with 38 years’ experience in senior management, operations, IT, marketing, administration and corporate affairs. She is responsible for the day-to-day operations and oversees and manages marketing, underwriting, accounting, audit, risk management, client and regulator relations, client acquisition and retention, regulatory compliance, government affairs and corporate communications and standards. 

She is a respected industry leader and her experience includes procurement, management and team oversight of complex national and global risk management clients and projects using her authoritative experience in the feasibility, formation, licensing and ongoing management of captives.

Louie's extensive background across various forms and types of captives in numerous domiciles positions her as a leader with both national and global insights. Her unique skill set has not only made her an engaged leader but also a sought-after speaker and commentator at industry conferences, meetings and publications. She affects positive change, supporting the next generations of leaders and uplifting and empowering women in all disciplines of captive insurance.

Currently serving as chairwoman of the Western Region and holding directorial roles within the Nevada Captive Insurance Council and Oklahoma Captive Insurance Association, two- term board member of ICCIE and two-term board member, including secretary, treasurer, vice chair and chairwoman of CICA, serving 2018-23 as well as on several state legislative committees. She is a member of CALC and NRRA and is deeply committed to advocating for stable legislation across all domiciles. 

Her dedication has earned her recognition as one of the top 50 most powerful and influential leaders in the captive industry for several years running. Her leadership skills are complemented by her proactive approach to fostering innovation and game-changing progress. Under her guidance, the firm is expected continued growth and forward-thinking strategies employing continued excellence with best practices as CEO of her highly respected organisation.

Nate Reznicek, president, Captives.Insure

Reznicek, ACI leads one of the largest independent captive insurance programme managers in the world. Headquartered in Tennessee, CI provides brokers and captive managers with AM Best-rated global captive insurance solutions through its open programmes and delegated underwriting authority – giving them the tools and expertise confidently to win new business and retain key accounts without sacrificing commissions or revenue.

A well-recognised captive expert, Reznicek serves on several boards and committees for major associations and international conferences. He is a founding adviser to the 831(b) Institute and a director and faculty member at the International Center for Captive Insurance Education (ICCIE), where he teaches the “Forming and operating a captive” course. Brokers and captive managers across the globe rely on Reznicek as a trusted subject matter expert on captive insurance strategy and operations.

His contributions to the industry have earned widespread recognition, including the Risk & Insurance® Power Broker® designation, the Captive Review Power 50, and honours from Business Insurance, US Captive Services Awards and Captive International. He has also been named in the Top 100 Best Insurance Leaders in the US and the Top Global Reinsurance Professionals Hot List.

A frequently requested speaker and published author featured across industry media and at conferences nationwide, Reznicek delivers clear, data-driven perspectives on captive strategy and market trends – translating complex risk management and insurance company operations into practical, actionable insight.

Gary Osborne, vice president, Risk Partners

Osborne joined Risk Partners as vice president of Alternative Risk programmes in 2018. He has 40 years of captive experience having worked in four different domiciles (Bermuda, Vermont, Hawaii and South Carolina). He has also been involved in writing parts of the captive laws in South Carolina and Tennessee and has previously been a faculty member of ICCIE (International Center for Captive Insurance Education).   

His career began in 1982 on the audit staff of Deloitte Haskins and Sells, followed by senior auditing role at Price Waterhouse. Osborne then enjoyed progressive responsibilities while managing captive portfolios at Marsh & McLennan (Bermuda) then Johnson & Higgins (Vermont). He was then hired by Sedgwick to establish a captive management operation in Hawaii. After Sedgwick outsourced captive management to USA Risk Group in 1995, Osborne held various management positions there, including president from 1995-2018. He was responsible for all aspects of company operation including expanding the company through acquisitions, overseeing captive management and financial operations.

He has often been featured in Captive Review, Risk Retention Reporter, Captive Insurance Times 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, Tennessee Captive Insurance Association,  director, South Carolina Captive Association (former chairman and current committee member), 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. He was inducted into the Captive Hall of Fame in 2019 and recognised as Captive Professional of the year in the same year by Captive Review.

Phillip Giles, Chief growth officer, accident and health, Skyward Specialty Insurance

Giles has more than 30 years of accident and health and property and casualty alternative risk experience and has been in his present post since July 2024.

He 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.

Anne Marie Towle, chief executive officer, Hylant Consulting

A veteran of the captive and global insurance industry, Towle was promoted in 2025 to lead Hylant’s global consulting practice, which includes analytics, business risk consulting, captive management and consulting, M&A and transaction solutions, and outsourced risk and consulting services. She specialises in developing customized solutions for complex insurance and risk-financing challenges. Internationally recognised with numerous industry awards, she is a tireless leader with a diverse set of skills and experience.

Trained as a CPA, her true gift is translating complex concepts into simple terms for non‐insurance professionals while also communicating seamlessly with CFOs and other financial leaders.

Towle is a key member of Hylant’s leadership team, known for building and strengthening the firm’s consulting practice. Since joining Hylant in 2019, she has developed the global captive solution division into an industry leader recognised for thought leadership, collaborative client partnerships and innovative strategies. She promotes a culture of growth through ambitious goals and continuous education, and under her guidance, the team consistently delivers exceptional client service. In 2023, she expanded her global role by leading the global risk team in addition to the global captive team.

Prior to joining Hylant, Towle spent ten years in public accounting, assisting clients with tax structuring and compliance across the insurance sector. She also worked at large international brokerage organizations guiding clients through global risk consulting, risk analytics and captive structuring solutions. Customised solutions remain her specialty. She has supported clients in healthcare, construction, real estate, manufacturing, marine, oil and gas, private equity and professional sports and entertainment to manage their total cost of risk. A dynamic leader, Towle is dedicated to creating strategies that transform risk into measurable value on clients’ balance sheets.

She excels at designing impactful, customized solutions and thrives in collaborative environments where teams work relentlessly to achieve the best outcomes for clients and colleagues.

Towle serves on the Hawaii Captive Insurance Council, is a past chair and founding member of CICA’s Amplify Women and is on the ICCIE curriculum committee and faculty. She previously served on the VCIA board (2017–23) and the ICCIE Board (chair in 2023) and has contributed to conference committees for VCIA, CICA, WCF, SCCIA and HCIC.

Sandy Bigglestone, chief governance, regulatory and compliance officer and managing director, SRS Titanium

As SRS Titanium’s managing director and chief governance, regulatory and Compliance (GRC) officer, she brings a wealth of knowledge and experience. Sandy focuses on providing SRS clients with strategies for regulatory and GRC standards within their captives. Using these strategies helps clients make the most of their captives for their overall business success.

Bigglestone has been with the Vermont Department of Financial Regulation’s captive insurance division since 1997. She was appointed as deputy commissioner effective September 1, 2022 after serving as her predecessor’s principal staff member for 14 years.

In 2018, she received of the Women to Watch Award by Business Insurance for her leadership, expertise and accomplishments in the captive insurance industry.

In 2024, Bigglestone was nominated and selected as one of the top 50 female leaders in the captive industry by Captive International. The 2024 and 2025 Captive Review Power 50, which recognises the most influential professionals in the global captive insurance industry, named Bigglestone at #1.

Mikhail Raybshteyn – insurance tax and alternative risk finance strategy consultant

Raybshteyn brings more than 20 years of experience advising global insurance, reinsurance, captive insurance, InsurTech and financial services organisations to the table. Prior to 2026 he served as a tax partner in a big four accounting firm’s global insurance sector, where he held key leadership roles including Americas captive insurance services co-leader and US Northeast InsurTech tax services leader.

His practice focuses on insurance and tax planning, structuring, risk advisory, tax controversy and regulatory matters across traditional and emerging insurance markets. He has extensive experience guiding clients through the design, formation, utilisation and restructuring of captive insurance and InsurTech programmes and structures, as well as evaluating and developing insurance products for captive insurance companies.

Widely recognised in the industry, Raybshteyn has been named multiple times to the Power 50 list of leading captive insurance professionals. He is also a recipient of the NYS Society of CPAs and Captive International’s FORTY Under 40 awards and has been inducted into Marquis Who’s Who in America.

Grainne Richmond, EVP, head of captives, Aon

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.

Heather McClure, managing partner and general counsel, Helio Risk

Heather McClure has decades of experience managing client risk inside law firms and organisations, overseeing risk financing, risk management, insurance procurement, captive operations, and claims and litigation.

Prior to joining Helio, McClure was chief risk adviser for the national healthcare practice at Aon, a global risk and insurance services company. Prior to that role McClure was chief risk officer at the University of Oklahoma’s health system, directing risk, claims, captive operations and insurance structure, including property, cyber, directors’ and officers’, employer liability, workers’ compensation, provider professional liability, hospital liability, aviation, auto and all other commercial and captive lines. McClure also served as chief legal officer of the system’s captive insurance company, saving the system millions over its years of highly successful operations.

McClure’s career began as a trial lawyer defending organisations and medical providers in the law firm setting, trying multiple cases to juries as lead counsel. After ten successful trials, she began a career as in-house counsel to a large organisation in Texas, managing people and processes related to risk, claims and litigation.

McClure earned a BA in journalism with a political science minor and a juris doctorate from the University of Oklahoma and a post-doctorate master of laws (LL.M.) degree in health law from DePaul University, Chicago. She holds certifications as a professional in healthcare risk management (CPHRM) from the American Society of Healthcare Risk Management and a mediator certification from Southern Methodist University in Dallas. She is licensed as a lawyer in Oklahoma, Texas and Vermont and has insurance producer licenses in Oklahoma and Texas. She earned the associate in captive insurance (ACI) designation from the International Center for Captive Insurance Education (ICCIE), the world’s foremost provider of captive insurance education, in June 2024.

McClure was elected by the captive industry as Captive Review’s U.S. Captive Risk Manager of the Year in 2020 and was voted by peers to be #27 on its Power 50 list. She is a former board member and chair of the Vermont Captive Insurance Association and is a current board member of Captive Insurance Companies Association (CICA), the world’s largest non-domicile industry association for captives globally. In March 2023, McClure was elected to an executive officer position with CICA’s board of directors.

McClure’s expertise includes providing risk financing and operational solutions for all industries including insurance programme analyses, commercial and captive structure and operations, alternative risk transfer, creating endorsements and policy forms to address evolving risk and claims advocacy support. She teaches classes, speaks at industry events, and publishes numerous articles on risk and liability issues and operational best practices for risk financing programmes across the country and internationally.

McClure is involved in community volunteer opportunities with homelessness and animal rescue. She is passionate about serving clients by assessing, advising and facilitating risk strategy, as well as facilitating broader culture change, implementation of best practices, and reduction of organisational risk.

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.

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