Discover Leadership Cayman: Free Info Sessions Open for 2026 Applicants
The Cayman Islands Chamber of Commerce invites all aspiring leaders to attend one of four free Leadership Cayman Information Sessions this October and November to learn more about the transformative six-month programme.
The sessions follow a Leadership Cayman Alumni Reception, where prospective students for Leadership Cayman’s class of 2026 got to talk with members of the alumni about the programme and what it offers.
The upcoming sessions are the perfect opportunity to hear directly from alumni, meet programme organisers, and discover how Leadership Cayman can help you take the next step in your personal and professional journey.
Upcoming Information Sessions:
Wednesday, 22 October (Virtual via TEAMS) | 12:30 PM – 1:30 PM
Register: https://web.caymanchamber.ky/events/Leadership-Cayman-Information-Session-Teams-Meeting--6436/details
Monday, 27 October (Virtual via TEAMS) | 12:30 PM – 1:30 PM
Register: https://web.caymanchamber.ky/events/Leadership-Cayman-Information-Session-Teams-Meeting--6437/details
Monday, 3 November (In Person) | 5:15 PM – 6:15 PM
Register: https://web.caymanchamber.ky/events/Leadership-Cayman-Information-Session-In-Person--6438/details
Wednesday, 5 November (Virtual via TEAMS) | 12:30 PM – 1:30 PM
Register: https://web.caymanchamber.ky/events/Leadership-Cayman-Information-Session-Teams-Meeting--6440/details
What is Leadership Cayman?
Launched in 2009 by the Cayman Islands Chamber of Commerce, Leadership Cayman is a dynamic, immersive programme designed to cultivate the next generation of community-minded leaders. Over six months, participants attend bi-weekly seminars that explore the most pressing social, economic, business, and political issues facing the Cayman Islands.
“Leadership Cayman isn’t just about learning leadership theory,” said Melissa Whorms, Chair of the 2026 Planning Committee and a 2021 graduate, “It’s about experiencing leadership in real time — through the lens of our community and the people shaping it every day.”
Participants engage directly with top-level decision-makers, ask meaningful questions, and build a network of peers who challenge and support one another. The programme is designed to foster not only knowledge, but confidence, connection, and purpose.
Whether you’re curious about the time commitment, wondering if you’re eligible, or simply want to hear what past participants have to say, the free information sessions are the best way to explore whether Leadership Cayman is right for you.
“If you’re ready to challenge yourself, expand your thinking, and become part of a deeply engaged community of change-makers – now’s the time to act,” said Chamber CEO Wil Pineau. “Applications for the 2026 class are open, and we encourage you to take that step. It’s an investment in your future – and in the future of these islands.”
Who Should Apply?
Leadership Cayman is open to individuals who are 25 years or older, have been legally resident in the Cayman Islands for at least one year, and are currently serving in middle management or higher within their organisation. The programme is ideal for professionals who are ready to deepen their understanding of the Cayman Islands, expand their leadership capacity, and connect with a diverse network of peers across sectors.
Sidney Terry, who works in the Ministry of Education’s IT Support Unit, attended the recent alumni reception at the Lobster Pot
“I’ve had friends go through the programme, and I’ve been interested for a while,” he said. “As a Caymanian and a blossoming leader, I’m especially excited about the deep dive into Caymanian culture and history — and the chance to understand how our nation really works,” he said.
Don’t miss your chance to be part of something bigger.
Join a free info session and take the first step toward Leadership Cayman 2026. You can register at the links provided above,