George Town, Grand Cayman, Cayman Islands (25 September 2026) – Cayman Islands Tech Futures Week returns from 5–9 October 2026, bringing together government, industry, educators, employers, entrepreneurs and the wider community for six days of conversations, workshops and events focused on how artificial intelligence is changing the way Cayman works, learns, does business and competes.
Delivered through a public-private partnership between Workforce Opportunities & Residency Cayman (WORC), the non-profit Enterprise Cayman, and Cayman Enterprise City (CEC), this year’s programme is centred on the theme The AI Advantage and is designed to turn discussion about AI into practical action for Cayman’s workforce, businesses and community.
New for 2026 is the Tech Futures Innovation Summit, a full-day conference taking place on Tuesday, 6 October at the Harquail Theatre and Studio Theatre. The Summit will bring Cayman’s technology, business, investment and entrepreneurial communities together to examine the practical impact of AI on business operations, entrepreneurship, financial services, and workforce development. The programme will also feature a Reverse Pitch connecting founders with investors and service providers, followed by Pitch & Sip, showcasing emerging Cayman based AI ventures.
Throughout the week, a series of targeted focus groups will invite community groups to share their perspectives on the opportunities, challenges and safeguards that should inform Cayman’s response to AI. Discussions will explore issues including employment and skills, recruitment and talent development, how young people are using AI, and how Cayman’s education and training system can prepare students for an increasingly AI-enabled economy.
The programme begins on Monday, 5 October with Building an AI-Ready Cayman, a breakfast roundtable bringing leaders from government, industry, education and the wider community together to identify priorities around skills, infrastructure, governance, digital trust and responsible AI adoption.
Other programming across the week includes practical AI workshops, CyberSandbox activities and a “Tech Talks” discussion on AI governance and risk. An online, Mastering AI Prompts, workshop will also give participants practical techniques for getting better results from AI tools, with no technical background required.
Reinaldo Fletcher, Manager Labour Market Demand Unit (LMDU) at WORC, said the partnership reflects the importance of connecting technological change directly with Cayman’s workforce priorities. “Tech Futures Week 2026 directly aligns with the vision of the Labour Market Demand Unit (LMDU) at WORC, that is, to champion a globally-competitive Caymanian workforce through the dissemination of labour market information. Technological change is one of the five major drivers expected to transform the global labour market by 2030 according to the World Economic Forum. Furthermore, Artificial Intelligence (AI) and Big Data is the top-ranked skill on the rise from 2025 – 2030. These trends highlight the significance technology, and in particular AI, has and will have on the current and future workforce needs of the Cayman Islands. Therefore, it is critical the LMDU continues to collaborate with Cayman Enterprise City through Enterprise Cayman on Tech Futures Week to gain insights from local technology experts to inform workforce development initiatives, and ultimately, prepare Caymanians for the future of work,” explained Reinaldo.
Alyssa Manderson, Programme Manager at Enterprise Cayman, said the programme has deliberately been designed to combine big-picture conversations with practical opportunities to participate. “Tech Futures Week is about bringing diverse perspectives together, giving individuals meaningful ways to engage with the technology, and start asking what Cayman needs to put in place now to benefit from the opportunities ahead.”
Access Over Ticket Revenue
All Tech Futures Week programming is free to attend, reflecting the initiative’s community education and workforce-development mandate.
Partners have prioritised broad access so that cost does not become a barrier to participation. The approach is intended to widen access to knowledge and skills, bring more community perspectives into the conversation, and ensure that Cayman’s evolving innovation ecosystem is accessible to the people and organisations that can benefit from it.
“Technology will continue to change, and Cayman’s ability to respond cannot depend on a small group of people understanding what is happening,” Manderson added. “Building capability means creating opportunities for individuals to learn, ask questions, contribute their perspectives and experiment with these tools themselves.”
Tech Futures Week 2026 takes place Monday, 5 October through Friday, 9 October 2026.
The programme includes:
Monday, 5 October: Building an AI-Ready Cayman Breakfast Roundtable and Caymanian Perspectives on an AI-Enabled Future Focus Group
Tuesday, 6 October: Tech Futures Innovation Summit at the Harquail Theatre and Studio Theatre
Wednesday, 7 October: AI in Recruitment & Talent Development Focus Group, CyberSandbox and Raising the AI Generation Parents Focus Group
Thursday, 8 October: Mastering AI Prompts online workshop and Tech Talks: Power, Risk & AI Governance
Friday, 9 October: Preparing Students for an AI Future Education & Training Focus Group
Participation is free, although advance registration is required for many sessions as capacity may be limited.
For the full programme and registration details, visit enterprisecayman.ky/tech-futures-week.
Photo Caption: Tech Future Week Committee 2025, L-R Deajra Tulloch, Saschelle Ricketts, Ashema Edwards, Ana Chisholm, Charlie Kirkconnell, Reinaldo Fletcher, Kaitlyn Elphinstone, Alyssa Manderson, Adriaan Duvenage