FutureMe Cayman: A New Approach to Career Planning

Innovative platform designed to help Caymanians link life goals with realistic training pathways and job opportunities.
Grand Cayman, Cayman Islands (10 December 2025) – Caymanians and residents can now explore career paths in a new way with the launch of FutureMe Cayman, a lifestyle-led career mapping platform. Designed to help users make confident decisions about their future, the platform is set to make career planning more accessible, more personal, and more realistic for anyone thinking about their next step.
At its core, FutureMe Cayman flips the usual career planning process. Instead of diving straight into job titles, the platform asks users to start with the life they hope to lead, whether that’s owning a home, travelling often, supporting a family, or finding balance. It then maps those lifestyle goals to realistic career options and outlines the training, scholarships, and job opportunities available to support them. These insights are drawn directly from Workforce Opportunities and Residency Cayman (WORC), the Economics and Statistics Office (ESO), and Cayman Resident, ensuring the platform is grounded in accurate, local, and up to date information.

FutureMe Cayman Platform Launch Event. L-R: Hon. Michael S. Myles, David Manouchehri, Mary Davies, Shannon Williams, Saschelle Ricketts, Reinaldo Fletcher, Ashema Edwards, Charlie Kirkconnell, and Alyssa Manderson
The platform also introduces several practical features designed to help users understand their options at a glance, including: local salary data to show realistic earning potential, WORC job integration to highlight roles currently available in Cayman, mastery analysis to help them focus on skills that matter most, and lifestyle alignment tools that prioritise careers that genuinely fit the life they want to lead.
“As a community we often talk about the importance of innovation and supporting our future workforce, but FutureMe Cayman shows what can happen when those conversations turn into action. In just two months, Cayman’s tech community volunteered their time and talent to successfully build and launch a high-impact app that will genuinely help people plan their future. We are grateful to Cayman Enterprise City for sponsoring the resources and space to make this collaboration possible,” said Reinaldo Fletcher, Labour Market Demand Unit Manager at WORC.
The platform began taking shape during the 2025 Tech Futures Hackathon Challenge that took place on 11 October 2025 at Cayman Enterprise City’s Signal House facility. During the event, produced by the Cayman Islands Computer Science Society (CICSS), WORC, and Enterprise Cayman, eight teams created a range of prototypes aimed at supporting Cayman’s future workforce. The winning project, “Mentor Map”, created by Shannon Williams and Mary Davies, stood out for its thoughtful design and practical approach and later became the foundation for FutureMe Cayman. Many of the other hackathon participants continued contributing during two follow-up development sessions, helping to shape the version that has now launched to the public.
“My path wasn’t straightforward. I made mistakes figuring out what I wanted to do, and I was lucky I had mentors who helped me course correct. But not everyone has that access. That’s why an app like this makes sense. It levels the playing field so everyone gets the same information and tools to plan their next step,” said Shannon Williams, Winner of the 2025 Tech Futures Hackathon Challenge. “This isn’t another ChatGPT wrapper. It’s a complete AI-powered system that helps you decide what career fits your life and shows you how to get there using real market data.”
FutureMe Cayman signals a major step forward for Cayman’s innovation community, offering a practical tool that supports long-term workforce development and helps residents plan for a future built around their goals and aspirations. “Together, FutureMe Cayman and the Tech Futures Week 2025 Report highlight a shared momentum across the Islands to support innovation, strengthen talent development, and create opportunities for Caymanians in emerging fields,” said Alyssa Manderson, Programme Manager at Enterprise Cayman. “Both initiatives show what’s possible when the community’s ideas and energy are channelled into practical tools and long-term planning.”
“FutureMe Cayman is an excellent example of what can be accomplished through public private partnerships, in this case resulting in a platform that will help Caymanians make informed career and career training decisions based on real local data, maximising their prospects of career success and life satisfaction,” said Charlie Kirkconnell, CEO of Cayman Enterprise City and Chairman of Enterprise Cayman. “FutureMe Cayman and the annual Tech Futures Week initiative that enabled its creation represent the continuation of a sustained effort to build a vibrant, sustainable innovation ecosystem where Caymanians not only participate, but thrive.”
To learn more and access the FutureMe Cayman platform, please visit futureme.ky.
The Cayman Islands 2025 Tech Futures Week Report is a comprehensive summary of the insights, conversations, and recommendations gathered during Tech Futures Week 2025. To access the report please visit https://www.enterprisecayman.ky/tech-futures-week.
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About Enterprise Cayman
Enterprise Cayman is a non-profit organisation (NPO) powered by Cayman Enterprise City in partnership with Cayman Islands’ special economic zone companies (SEZCos). The organisation, which applies the Theory of Change (TOC) methodology, provides Caymanians and residents with access to high-quality learning experiences and opportunities to develop and launch new business ventures, to pursue careers within the technology and innovation sectors, and to join a dynamic network of industry professionals. Let’s grow the next generation of Caymanian innovators and entrepreneurs with Enterprise Cayman!
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