Captive International Cayman Awards


Captive International Cayman Awards

Welcome to the results of the inaugural Captive International Cayman Awards. In the following pages we reveal the results of a comprehensive survey conducted over many months designed to identify the most influential and highly regarded firms and individuals operating in the market.

Across the following pages, Captive International is delighted to unveil the findings of our inaugural awards.

These results are the culmination of a three-month long research project into the captive Insurance sector in Cayman. Our goal was to identify the leading companies and individuals working in or contributing to Cayman’s vibrant captive community.

To achieve this, we used a mix of online surveys sent to readers of Captive International and phone interviews with select contacts who have been developed since 2004 when we first published Cayman Captive magazine.

The aim of the survey was to gain a detailed understanding of which companies and individuals are highly regarded within their respective fields—and why. We have tried to include the full breadth of services frequently used by the captive insurance community, from actuaries and accountants to investment managers and bankers.

We hope this gives a holistic picture of the Cayman captive insurance market, showcasing an Island that is renowned for the quality and quantity, and the depth and breadth, of its service provider community.

We have used both quantitative and qualitative measures in our analysis—looking at how many votes each company or individual received, as well as assessing what value scores were given to them.

We asked survey participants why they made the choices they did. This ensured that our results were not dominated by the largest companies only. We were also able to identify companies with a smaller client base who provide an exceptional level of service.

Once all the votes were counted, our editorial team sense-checked each vote and interview notes, validating all votes by unique contact details and removing votes where people had nominated themselves. We then calculated results that factored in both the pure number of votes and the qualitative scores.

We were keen that this research project would represent more than simply a popularity contest determined by market share alone. This was the reason we always asked respondents why they chose certain companies and asked them to score their choices based on service levels. This allowed respondents to comment on quality regardless of market share.

Spheres of influence

The feedback we received illustrates the interconnected nature of today’s captive insurance industry. Cayman’s captives community is influential far beyond the geographical limits of its shores, while people and institutions outside Cayman are also influential on the Island.

Accordingly, among those nominated for awards are executives who live and work outside Cayman itself, but who do a significant amount of business with Cayman-based captives, and are well-known figures there.

After years of industry consolidation, the days of smaller, boutique institutions operating exclusively in Cayman, or any other single jurisdiction, are all but over. Some institutions, which are highly commended for awards, originated in Cayman, before their success led them to establish operations elsewhere. Many others represent the Cayman presence of global firms—but their expertise is local.

For local understanding remains crucial. Every jurisdiction has its own personality, and Cayman is no exception. A first-hand experience of the Island’s legal requirements and cultural nuances is essential to any service provider’s success.

In today’s market many combine the resources and reach of a global company with the local knowledge and contacts of a local player, to powerful effect. Firms such as Milliman, Artex and KPMG are as much a part of the fabric of Cayman as any firm.

The success of any firm often comes down to personal relationships, and the Captive International Cayman Awards recognise some of the best known and most admired figures in Cayman’s captive insurance community.

Captive managers such as Kevin Poole, lawyers such as Derek Stenson and accountants such as Dara Keogh represent global institutions, but live and breathe the Cayman captive insurance industry. Actuaries such as Al Rhodes may reside in the US, but the amount of business they do in and with Cayman makes them an intrinsic part of this dynamic and globally interconnected community.

Among the award-winners, and those who were highly commended, are some of the best-known names in the global insurance industry, as well as niche players that specialise in captives, or that do a significant proportion of their overall business in Cayman.

Regardless of their size and the breadth of their business, every person and institution named in the Captive International Cayman Awards has an intimate understanding of the captive insurance industry. Each knows what makes Cayman successful, and what it takes to do business there.

We feel that our survey and awards represent an honest and unbiased assessment of how different companies and individuals are perceived in terms of their different qualities.

We stress that the data does not represent the opinions of Captive International. But we are comfortable that our research process and methodology was comprehensive and detailed enough for this to present an accurate current picture of the market. 


Awards methodology explained

Responses were obtained via an online poll and phone interviews with select contacts developed since 2004 when we first published Cayman Captive magazine.

We asked respondents to name up to three firms or individuals (depending on the question) they have experience of working with based on their competence, expertise and innovation, rank them out of 10 (10 being the highest) and comment on the reasons for their votes.

Once all the votes were counted, our editorial team sense-checked each vote and interview notes, validating all votes by unique contact details and removing votes where people had nominated themselves.

This information allows us to plot a scatter graph indicating the number of votes received by firms and individuals, and how highly they are rated by those who voted for them.

We have published these graphs for the first two categories for illustrative purposes only, to show the depth of the data and featuring  a selection of the companies or individuals named. For illustrative purposes, we have rounded numbers down to the nearest 0.5 to make the results easier to understand and to plot on the graph.

To determine ‘winners’ from this methodology, we multiplied the number of votes they received by the qualitative score out of 10. We have published the top three in each category based on this methodology (a winner and two highly commended).

Below are the award categories. We list an edited summary of results here: for conciseness we have listed the winners only. Please click on the links to read more about the winners and highly commended runners-up. 

Captive management firm

Winner: Strategic Risk Solutions

Captive manager (individual)

Winner: Kevin Poole, deputy managing director, Artex

Law firm

Winner: Conyers


Winner: Derek Stenson, partner, Conyers

Accountancy, audit and tax advisory firm

Winner: KPMG

Accountancy, audit and tax advisory specialist

Winner: Dara Keogh, managing partner, Grant Thornton

Actuarial firm

Winner: Milliman

Actuarial specialist

Winner: Al Rhodes, owner and president, SIGMA


Winner: Butterfield

Banking specialist

Winner: Conor MacHugh, senior relationship manager, Scotiabank

Letters of credit firm

Winner: Comerica

Letters of credit specialist

Winner: Martin Ellis, senior vice president, manager, Comerica

Asset management firm

Winner: Performa

Asset manager

Winner: Hugh Barit, chairman and CEO, Performa

Feasibility firm

Winner: Marsh

Feasibility specialist

Winner: James Bulkowski, senior manager, EY

Reinsurance firm

Winner: Hannover Re

Reinsurance specialist

Winner: Phil Giles, vice president, sales and marketing, QBE

Fronting firm

Winner: AIG

Reinsurance broker

Winner: Marsh

Reinsurance broker specialist

Winner: Mark Landry, managing director, Marsh


The information published here is for general information purposes only. No responsibility or liability is accepted by Newton Media Limited for any loss to any person, legal or physical, as a result of any statement, fact or figure contained in this article and our survey results. While we endeavour to ensure the information is up to date and correct and that our methodology is representative of sentiment in the market, we make no representations or warranties of any kind, express or implied, about the completeness, accuracy, reliability or suitability of the companies mentioned here for any purpose. Any reliance you place on such information is therefore strictly at your own risk. In no event will we be liable for any loss or damage including without limitation, indirect or consequential loss or damage, or any loss or damage whatsoever arising from the information presented here. This publication is not a substitute for advice on a specific transaction.

The publication of advertisements does not represent endorsement by the publisher.

Captive International