At the age of 21, Tamsin Deasey-Weinstein – a director at the University College of the Cayman Islands – almost became a spy.
The now 45-year-old applied to join the British secret service, passed the intelligence testing and spent a day at the headquarters. Ultimately, however, she decided it wasn’t for her.
Did MI5 miss out on a potential spy extraordinaire? Deasey-Weinstein doesn’t think so.
“I am a terrible liar and cry at the drop of a hat so it probably wouldn’t have been well suited to me!”
Thankfully the Brit, who moved to the Cayman Islands in 2019, has a whole host of other skills and an extraordinary drive and zest for life that have seen her take on a huge range of challenging and impactful roles over the years.
Her background is marketing, with, in recent years, a focus on education, but she also has experience in business development and workforce strategy and is a passionate advocate and thought leader for AI.
She secured the UCCI role in March 2021, and currently spearheads internal and external communications, PR, events coordination, admissions and recruitment as well as overseeing the university’s daily operations.
Deasey-Weinstein is also a council member of the Cayman Islands Chamber of Commerce and co-chair of the National AI Education Steering Group and earlier this year published a national study on the future of Cayman’s workforce.
She says her “obsession” with AI started in 2022, when ChatGPT launched. Determined to learn all she could about the subject, she threw herself into online courses, read books and listened to podcasts, before eventually enrolling in a year-long AI course with Massachusetts Institute of Technology.
Deasey-Weinstein says what excites her most about AI is its potential to amplify human capability rather than replace it.
“Humans can never outpace AI in processing speed or data analysis, but AI makes our lives massively better by handling the routine tasks so we can focus on creativity, strategy, and human connection,” she explains.
“If we can learn to trust it, embed it and use it ethically, it can revolutionise not just our work but our lives. AI has the potential to eradicate diseases and help us to live longer, healthier, better lives.”
She says “of course” she has some concerns over AI, but as long as there are “robust ethical frameworks, proper regulation, and education” as well as a human-centred approach to AI development, where we don’t lose the human elements “that make life meaningful”, she remains fundamentally optimistic.
One of Deasey-Weinstein’s main career goals going forward, is to help ensure the whole Cayman community is ready for the future of AI.
“I want to work nationally to help Cayman upskill,” she says. “I want AI education embedded at every level, from primary school children learning computational thinking to executives understanding how to leverage AI strategically.
“I want to see Caymanians have future workforce skills that make them competitive globally while building industries that can thrive here locally.”
Helping to develop a thriving future workforce is something Deasey-Weinstein feels passionate about – and although AI is integral to achieving that, it’s part of a much bigger strategy, she says.
Over the past 15 years, both in the UK and on Cayman, Deasey-Weinstein has worked with the Chamber of Commerce, key employers and national bodies to develop training that, she says, employers need.
In the UK she used her research to open a studio school that drove work-based learning and skills building from the age of 11 rather than traditional classroom-based learning.
“It’s a new way of educating learners that are not necessarily skilled in testing and academics but highly proficient in skills needed for work,” she says.
“We were the second school of this kind to open in the whole of the UK, and I ended up running advisory work nationally for others wanting to do the same.”
Deasey-Weinstein also ran work-based apprenticeships programmes across the UK, working with thousands of students and employers to build bespoke pathways to plug regional skills gaps.
She hopes to introduce similar initiatives on Cayman.
“I have extensively researched and studied the adaptations needed for our work-skills pipeline over the past few years,” she says.
“If I can get the facts in front of decision-makers and support change to occur, then I have helped. Cayman is uniquely positioned to be a leader in future workforce development.
“We have the economic stability, the political will, and the small scale that allows for rapid implementation of innovative programmes.”
She says it’s important the territory diversifies its skills base to remain competitive globally, adding: “AI, tech and sustainable development all represent huge opportunities. But we need to start preparing our workforce now, not in five years when these changes have already happened.”
Among Cayman’s future workforce could be her own two children – an 11-year-old daughter and six-year-old son.
Unsurprisingly, AI has become a big part of their lives too. “I make them use it every day, we read stories on it, we do homework on it, we explore creative projects together,” says Deasey-Weinstein.
“But technology is just a tool and what I really want them to develop is curiosity, resilience, and empathy.
“I am focused on letting them see the world, be kind, be compassionate, think critically, care for others and understand it’s a big wide world with endless opportunities.”
In terms of future careers for her kids, she says: “My advice to them is always simple, find work that energises you rather than drains you. We spend most of our lives at work, so they must find their passion and follow it.”



