Our Story

The need for a captive insurance leader with integrity in the U.S. was evident in the early 1980s when bringing trust and confidence to new alternative risk solutions was vital to its success. This led to the company that would be called USA Risk Group to be formed in 1981 when our founder helped pioneer captive legislation in Vermont, which then became the first successful onshore domicile in the U.S.

We are the independent alternative risk advisor with proven integrity & innovative ideas that's been taking insurance in a new direction since 1981.

With our roots still strong in Vermont, we have continued pioneering the ever-growing captive insurance industry by expanding into multiple domiciles to ensure numerous solutions to the clients we serve. Our experienced team develops practical solutions for unique situations for middle to large market companies in all industries that are looking for additional options for insurance coverage, cost-savings, additional capacity, and more control of premium dollars.


Solving the challenges that each company presents allows us an opportunity to show our clients how to integrate cost-efficiencies to gain more control over their insurance and risk management programs. By remaining independent from broker or insurance company ownership, we can ensure we act as an advocate with unbiased solutions for an organization’s long-term goals.


Putting our Hearts into Your Business


We go beyond business as usual because no one on our team wants to work with nameless, faceless accounts. We get to know the people who made the choice to trust us with solving their business problems because when we know a person’s story and not just an account number, we feel more connected to their success. And that’s why we try harder and go the extra mile. Because there’s nothing like the satisfaction we feel when we put our hearts into helping our clients build something they value. Putting our hearts into your business. It’s what we do. 

Our Team


Stephen Roseman

CEO & President

Stephen is responsible for management of the company’s Operational Leadership Team, providing ongoing guidance, direction and strategic oversight of the long-term, client-centric growth strategy.

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Rob Leadbetter

Sr. Vice President - Cayman, BVI

In 2005, Rob joined the company as VP in the Cayman office. In 2017 he was promoted to Sr. VP of Cayman and BVI operations. He is the contact for Cayman clients and Insurance Dept. of Cayman Islands Monetary Authority.

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Jeanne Crawford

Sr. Vice President - Barbados

Jeanne joined USA Risk Group (Barbados), Ltd. in 1993. Throughout her tenure at the company she has held various management positions and in 2013 was promoted to Senior Vice President for the Barbados office.

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Paul Macey

Head of Captive Operations

Paul serves as Head of Captive Operations as well as President of USA Risk Group (Cayman.) He joined the company in 2005 as Senior Vice President and was promoted to President in July 2009.

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Joshua Jarvis

Chief Technology Officer

Joshua joined the company in 2008 as the Network Administrator and was appointed Chief Technology Officer in 2010. His focus is on the short and long-term business goals that require a secure and advanced environment.

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John Tortell

Vice President - Malta

John Tortell became director of USA Risk Group - Malta, Ltd. in 2010. He has been involved in the captive insurance industry in Malta since its entry into the European Union, being one of the first captive managers to be licensed.

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Paula Kenneson

Chief Financial Officer

Paula was named CFO in 2016 and is responsible for the financial management of the company, including financial reporting, accounting, treasury, and corporate functions for onshore and offshore member companies.

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Jennifer Hawkins

Vice President

Jennifer is responsible for corporate administration of the USA Risk Group member companies, serving as VP of Human Resources and compiling and submitting all new captive insurance company applications

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Contact Us

Visit our employee directory for our contact info and office locations

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