Jenn Cowdroy, Director

Jenn arrived in Cayman in January 1993 after a year long post graduation backpacking trip landed her on our shores, and she has called Cayman her home ever since. As a co-owner of both Island Primary and Island Montessori, Jenn manages the schools’ administration and accounting and is leading the development project to bring Island Primary to Cayman. Jenn has been working in Cayman for almost 30 years, holding senior financial and management roles in companies both large and small. Along the way her entrepreneurial drive has led her to open and manage several small to mid sized companies in the tourism, property and education industries. 

With an MBA in Finance, Jenn is also an Accredited Director under the Canadian Institute of Chartered Secretaries and has held director appointments on funds and operational companies over the last 15 years, while also serving as the Deputy Money Laundering Reporting Officer for a large fiduciary firm. With a keen interest in pension boards, Jenn was a trustee and chairwoman of the Chamber of Commerce Pension Plan from 2004 to 2010, before serving as a trustee of the Silver Thatch Pension Plan from 2012 - 2016.  

Jenn loves Cayman and all that it has to offer families who live here. It’s where she met her husband Brad, and where both her sons were born and raised and call home. She believes strongly in all that CaymanKind embodies and the strength that family and friends brings to our everyday adventures.