8 December 2020Cayman analysis

Captive International names the winners of the 2020 Captive International Cayman Awards

The winners of the Captive International Cayman Awards were selected based on responses to an online poll, as well as phone interviews with selected contacts, taking into account the effectiveness, efficiency and professionalism of institutions in a range of categories relevant to the industry.

In the second year of the Captive International Cayman Awards, USA Risk was named as the Captive Management Firm of the Year, with Willis Towers Watson, Strategic Risk Solutions, and Artex all highly commended.

SIGMA Actuarial Consulting Group has been named as both the Actuarial Firm of the Year and the Feasibility Study Firm of the Year, with Willis Towers Watson highly commended as a provider in both categories. Pinnacle was highly commended as an actuarial firm, while Aon was highly commended as a feasibility firm.

Conyers was named Law Firm of the Year, with Campbells and Walkers both highly commended, while Grant Thornton was named Accounting Firm of the Year, with RSM and PwC highly commended.

Scotiabank won the awards for Bank of the Year and Letters of Credit & Trusts Provider of the Year. Butterfield and Cayman National were both highly commended for the banking award, while Comerica and Wells Fargo were highly commended for their work providing letters of credit and trust services.

Graystone Consulting, part of Morgan Stanley, was named Asset Management Firm of the Year, with London & Capital and RBC both highly commended.

The Hartford won the award for Fronting Insurer of the Year, with Willis Towers Watson, Zurich and AIG all highly commended. Swiss Re was named Reinsurer of the Year, with Greenlight Re and United Insurance highly commended, while Willis Towers Watson was named Reinsurance Broker of the Year, with Kirkway International highly commended.

Individual awards

The Captive International Cayman Awards recognised the efforts and achievements of individuals working in or with the captive insurance industry in Cayman.

Lesley Thompson of Willis Towers Watson took home the individual award for captive management provider, with Paul Macey of USA Risk and Kevin Poole of Artex both highly commended.

It was a clean sweep for Conyers in the individual awards, with Derek Stenson named as the top lawyer, with Rob Humphries and Paul Scrivener, both also of Conyers, highly commended.

In the accounting category Grant Thornton’s Dara Keogh was named the winner, with Alan Shek of the same firm highly commended, alongside Damian Pentney of PwC.

Al Rhodes of SIGMA Actuarial Consulting Group won the individual prize for his work as an actuary and for offering feasibility services. Joe Herbers and Robert Walling, both of Pinnacle, were highly commended as actuaries, while Bruce Whitmore of Willis Towers Watson and Adrian Lynch, who at the time was at Aon Cayman, were both highly commended for feasibility services.

Marcus Stafford and Conor McHugh of Scotia were named as winner and highly commended, respectively, for the individual banker award, while Marty Ellis of Comerica was also highly commended.

Steve Gaziano of Morgan Stanley won the individual award for asset management, ahead of Lisl Lewis of London & Capital who was highly commended.

The Hartford’s Joe Lucy won the individual award for fronting services, with Bob Gagliardi of AIG and Todd Cunningham of Zurich both highly commended.

For reinsurance services, Tim Adair from United Insurance took the top spot, ahead of Robley Moor of Swiss Re and Jim Ehman of Greenlight Re, who were both highly commended.

For reinsurance brokerage services, Michael Woodroffe of Kirkway International was named winner of the individual award, while Scott Strenge and Paul Herriott, both of Willis Tower Watson, were highly commended.

The full list of the awards is as follows:

Captive Manager: Firm

Winner—USA Risk

Highly Commended—Willis Towers Watson

Highly Commended—SRS Highly Commended

Highly Commended—Artex Highly Commended

Captive Manager: Individual:

Winner—Lesley Thompson, Willis Towers Watson

Highly Commended—Paul Macey, USA Risk

Highly Commended—Kevin Poole, Artex

Law Firm


Highly Commended—Campbells

Highly Commended—Walkers


Winner—Derek Stenson, Conyers

Highly Commended—Rob Humphries, Conyers

Highly Commended—Paul Scrivener, Conyers

Accounting, Audit or Tax Advisory: Firm

Winner—Grant Thornton

Highly Commended—RSM

Highly Commended—PwC

Accounting, Audit or Tax Advisory: Individual

Winner—Dara Keogh, Grant Thornton

Highly Commended—Damian Pentney, PwC

Highly Commended—Alan Shek, Grant Thornton

Actuarial: Firm

Winner—SIGMA Actuarial Consulting Group

Highly Commended—Pinnacle

Highly Commended—Willis Towers Watson

Actuarial: Individual

Winner—Al Rhodes, SIGMA Actuarial Consulting Group

Highly Commended—Joe Herbers, Pinnacle

Highly Commended—Robert Walling, Pinnacle



Highly Commended—Butterfield

Highly Commended—Cayman National

Banking: Individual

Winner—Marcus Stafford, Scotiabank

Highly Commended—Conor McHugh, Scotiabank

Highly Commended—Marty Ellis, Comerica

Letters of Credit & Trusts: Firm


Highly Commended—Comerica

Highly Commended—Wells Fargo

Asset Management: Firm

Winner—Morgan Stanley/Graystone Consulting

Highly Commended—London & Capital

Highly Commended—RBC

Asset Management: Individual

Winner—Steve Gaziano, Morgan Stanley

Highly Commended—Lisl Lewis, London & Capital

Feasibility Study: Firm

Winner—SIGMA Actuarial Consulting Group

Highly Commended—Willis Towers Watson

Highly Commended—Aon

Feasibility Study: Individual

Winner—Al Rhodes, SIGMA Actuarial Consulting Group

Highly Commended—Bruce Whitmore, Willis Towers Watson

Highly Commended—Adrian Lynch, Aon Cayman

Fronting: Firm

Winner—The Hartford

Willis Towers Watson

Highly Commended—Zurich

Highly Commended—AIG

Fronting: Individual

Winner—Joe Lucy, The Hartford

Highly Commended—Bob Gagliardi, AIG

Highly Commended—Todd Cunningham, Zurich

Reinsurer: Firm

Winner—Swiss Re

Highly Commended—Greenlight Re

Highly Commended—United Insurance

Reinsurer: Individual

Winner—Tim Adair, United Insurance

Highly Commended—Robley Moor, Swiss Re

Highly Commended—Jim Ehman, Greenlight Re

Reinsurance Broker: Firm

Winner—Willis Towers Watson

Highly Commended—Kirkway International

Reinsurance Broker: Individual

Winner—Michael Woodroffe, Kirkway International

Highly Commended—Scott Strenge, Willis Towers Watson

Highly Commended—Paul Herriott, Willis Tower Watson