Tamsin Deasey-Weinstein, director at the University College of the Cayman Islands (UCCI) and member of the Cayman Islands Government’s NCFC National Digital Transformation Task Force, has returned from the first module of Oxford University’s Executive Diploma in Artificial Intelligence for Business with strategic partnerships that will support Cayman’s national AI strategy development.
The highly competitive one-year programme at Oxford’s Said Business School brought together 66 senior professionals from 25 countries, including Hong Kong, Singapore, Dubai, and across Europe and the United States. The cohort included leaders responsible for digital transformation in the UAE and Greece, as well as executives managing AI implementation for major global enterprises such as Apple, Microsoft and Google.
“I sat at tables with the person leading digital transformation for the United Arab Emirates, the architect of Athens’ digital strategy and executives managing AI implementation for some of the world’s largest enterprises,” said Deasey-Weinstein. “These aren’t just contacts, they’re potential collaborators who now understand what Cayman is doing, and the unique challenges small island nations face in the AI transition.”
The programme covered strategy and data architecture, ethics and governance, the evolving legal landscape of AI, and implementation approaches ranging from process automation to complete business transformation. Guest speakers from San Francisco, Chicago and Hong Kong shared how major enterprises are deploying AI at scale. Participants also experienced emerging technologies including Apple’s Vision Pro 2 spatial computing system.
Deasey-Weinstein emphasised that Cayman has distinct advantages in the AI transition that many larger nations lack. “Our size allows for agility, our international business expertise provides relevant foundations, and our community is small enough that we can genuinely include everyone in this conversation,” she said. “What I learned at Oxford is that the most sophisticated AI solution isn’t always the right one, understanding when each approach makes sense is critical, especially for resource-conscious environments like ours.”
The expertise gained at Oxford is being applied directly through a number of channels including the national AI strategy being developed by the NCFC National Digital Transformation Task Force, and the community-based ‘AI Monthly Meet Up Cayman’ initiative that Deasey-Weinstein organises independently to help the Cayman community learn about AI.
“I set up the AI Monthly Meet Up late last year because the Cayman community were asking me for help to learn and I care passionately about everyone having access to AI education. There is a huge opportunity for AI to shape our lives for the better and we all need networks to share and develop. This series exists because of what people in Cayman have told me repeatedly: they know AI matters, but they don’t know where to start,” said Deasey-Weinstein. “We’re building a space where anyone can learn, judgment-free, whether you’re technical or non-technical, private sector, public sector, education, or simply curious. I am very lucky to have the AI education that I have and this is my way of giving back and helping others to also get an AI education. It is now and will always be completely free so there’s no barriers to access.”
Next AI Monthly Meet Up
The next AI Monthly Meet Up Cayman takes place Thursday, 12 Feb. 2026 at 6:00 pm online, featuring global speaker Isar Meitis, CEO of MultiplAI.ai and host of the international ‘Leveraging AI’ podcast. Meitis specialises in translating AI developments into practical, immediately applicable business implementation. The hands-on workshop will cover real examples of how professionals use AI daily, safe and effective prompting patterns for business tasks, and repeatable workflows applicable immediately to communication, analysis, planning and administrative work. No technical background is required and attendance is free. The initiative has grown rapidly since launching in November 2024. The last session drew global participants and featured Dr. Harvey Castro, an international keynote speaker and physician focused on AI in healthcare. A further session featured the NCFC National Digital Transformation Strategy Task Force discussing Cayman’s broader push toward AI-enabled transformation.
Planned topics for upcoming monthly sessions include AI agents and automation, practical workflows for different professions, data protection and safe AI use, sector-specific applications across finance, legal, healthcare, education and small business, and the future of work and skills Cayman will need.
“I returned from Oxford exhausted but exhilarated,” Deasey-Weinstein said. “The week cost me sleep but gained Cayman something more valuable. A clearer picture of the path ahead, the relationships to help us walk it, and the conviction that this journey will make not only my future better, but our country’s future too.”
- Speaker: Isar Meitis, CEO of MultiplAI.ai
- Date: Thursday, 12 Feb. 2026
- Time: 6:00 pm Cayman Islands time
- Location: Online via Zoom
- Cost: Free (registration required)
- Registration can be completed online here.
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