6 December 2022Article

2022 Awards roll call

Cayman has always been a leader in the captive insurance world with the breadth and depth of expertise on the Island being unparalleled. We want to highlight this on the world stage so we launched our Cayman Awards.

The 2022 Captive International Cayman Awards are our tribute to the stars and unsung heroes of the captive insurance industry on Cayman. It is their efforts and achievements that keep Cayman at the forefront of the captive insurance world.

Over the past few months, Captive International readers have cast hundreds of votes in support of service providers they believe are at the top of their game.

Every year, each category of awards becomes more competitive than before. Given the highly contested nature of the categories, in most cases we have named two additional highly commended companies or individuals that were runners-up.

The awards are based on feedback received from across the captives industry, and in particular from readers of Captive International.

Respondents were asked to name up to three firms or individuals, depending on the question, that they have experience of working with based on their competence, expertise and innovation. Domiciles, firms and individuals were ranked out of 10, with respondents providing the reasoning behind their votes.

We’ve divided the company awards into categories covering the many businesses involved in captive insurance, from captive managers and reinsurance brokers to law firms. And, as always, we’ve included individual awards to ensure we recognise the accomplishments of leading individuals working in smaller organisations.

Congratulations to all the winners and the highly commendeds in each category.

We also thank those service providers who work around the clock for their clients, but did not attract as many votes this time around, and all those who took part in voting for these awards.

We look forward to building on this success for another year.

Captive Managers

The captive manager runs the insurance functions of the business on behalf of the captive owner. Securing the right captive manager is as crucial as naming the right person as chief executive of a business.

For those launching a captive with little experience of the insurance industry themselves, the captive manager can be a knight in shining armour. Perhaps the most crucial service provider to the owner of a captive, the captive manager bridges the gap in experience and expertise that those launching a captive may find themselves in need of.

Once again, Kensington Management Group has secured the award of Captive Manager of the Year, with the firm’s president Erin Brosnihan securing the individual award in this category.

Willis Towers Watson and Artex Cayman were highly commended as captive managers, with Lesley Thompson of Willis Towers Watson and Paul Macey of USA Risk highly commended for the individual captive management award.

Feasibility Services

A feasibility provider objectively assesses whether there is a good business case to be made for launching a captive, or whether the costs of establishing and managing the captive on an ongoing basis are likely to outweigh its benefits. This makes feasibility services vital for businesses considering the launch of a new captive.

Willis Towers Watson retained its title as the Feasibility Firm of the Year, with the firm’s Bruce Whitmore also retaining the individual award. SIGMA and Spring Consulting secured the highly commended spots for firms. SIGMA’s Al Rhodes and L. Michelle Bradley were highly commended as individuals.

Actuarial Services

Never underestimate the importance of actuaries—insurance can’t exist without the people and institutions that can accurately measure and price risk. It’s a function that most captives outsource to dedicated actuarial firms.

Retaining its title as Actuarial Firm of the Year was SIGMA Actuarial Consulting Group, while SIGMA’s Al Rhodes secured the individual award again. L. Michelle Bradley of SIGMA was highly commended. Milliman and Willis Towers Watson were highly commended as actuarial firms and Jeremy Pecora of Willis Towers Watson was highly commended as an individual.

Fronting Insurers

As a vital component of the broader captive insurance architecture, fronting services help captives and captive owners better manage their risk. Fronting gives captives the opportunity to partner with a reputable commercial carrier with a strong credit rating, allowing captives to reducing the cost of capital and offering their parents access to a broader range of services.

The Hartford took the top spot, being named Fronting Firm of the Year. Zurich North America and Concert Group were highly commended.


Having access to the reinsurance market is a key advantage of owning a captive, with many captive owners claiming this as a major factor for launching their captives in the first place.

This year, NorthEnd Re took the top award as Reinsurance Provider of the Year. Aureum Re was highly commended.

Fearghal O’Riordan of NorthEnd Re won the individual award for reinsurance professional of the year, with Phil Giles of MSL Captive Solutions being highly commended in this category.

Reinsurance Brokers

Reinsurance brokers offer crucial advice for captives on the hunt to secure the reinsurance provider that is the right fit for them and who addresses their individual needs.

Retaining its title, Willis Towers Watson was named the Reinsurance Broker of the Year. The firm’s Maryann McGivney won the individual award as a reinsurance broker.

Gallagher Re and Guy Carpenter were highly commended in the reinsurance broker category. Michael Woodroffe of Kirkway International and Stuart Tilghman of Gallagher Re were highly commended.

Accountancy, Audit & Tax Advisory

Having the right people managing the money is key for any business and captives, as legal entities distinct from their parent companies, require their own accountant to oversee their financial interests.

Grant Thornton has retained its title as Accountancy Firm of the Year, and Dara Keogh of Grant Thornton took home the individual award for accountancy again.

KPMG and Crowe were highly commended as firms, while Lawrence Kemp and Neil Maynard, both of Crowe, were highly commended as individuals.

Legal Services

At some point (and indeed at many points) in a company’s life, legal representation is needed. A captive insurance company is no different—from legal disputes with other service providers or policyholders to compliance with regulatory requirements, quality representation is key.

Walkers again took top spot as Law Firm of the Year, with Tony De Quintal of the firm taking home the individual award and Juliana Tang being highly commended.

Honigman was highly commended as Best Law Firm.

(Note: one or more law firms requested not to be featured in the results for this year's awards.)

Asset Management

While some captives may have the necessary investment expertise in-house, most require a dedicated asset management company to invest capital on their behalf. Captives generally require advice on investing assets in a way that balances the imperatives of generating returns and preserving capital.

Graystone Consulting (a wholly owned business of Morgan Stanley) took the top spot as winner of the Asset Management Company of the Year. Oppenheimer and Performa were both highly commended.

Steve Gaziano of Morgan Stanley was again named Asset Manager of the Year, with S Carl Terzer of CapVisor and Jack Meskunas of Oppenheimer highly recommended.

Banking Services

While the relationship between a captive and its bank has always been important, it has been especially important in the recent years of financial uncertainty. Through the provision of a range of financial advice and other services, banks are essential in allowing captives to function properly.

Scotiabank was named the Bank of the Year, after being highly commended last year. Butterfield Bank and Comerica were highly commended.

Scotiabank employees dominated the individual awards section, with Ivy Sahadeo winning the individual award and Marcus Stafford and Jonelle Campbell being highly commended.

Letters of Credit & Trusts

While banks generally provide a crucial service to captives, letters of credit and trusts are perhaps among the most important, offering captives financing for collateral and other purposes.

This year, Truist took the top prize, being named the Letters of Credit & Insurance Trusts Firm of the Year. Donny Tong of Truist secured the top spot in the individual award. Joe Monaco and Matthew Hornick, both of Truist, were highly commended.

Comerica and Scotiabank were highly commended for their performance in this area.


Captive consultants are central to the smooth running of captives—they coordinate and support captive owners across the entire of spectrum of requirements.

In this new awards category, Willis Towers Watson took top spot as Captive Consultant Firm of the Year, with Captive Resources and Spring Consulting Group highly commended.

Bruce Whitmore of Willis Towers Watson secured the individual award. Karin Landry of Spring Consulting Group and Donna Dreuth of Captive Resources were highly commended.