From UK to Cayman, a woman’s rise in AI leadership

Tamsin Deasey-Weinstein wakes up at 4:30 every morning. Those quiet hours are when she studies, writes or prepares for the day ahead. Later, after homework is finished and everyone is asleep, she begins a second round of work.

“I sacrifice lie-ins and TV, not family time,” she says of cherished moments with her loved ones.

Sheer determination has carried the director at the University College of the Cayman Islands and one of the Caribbean’s leading voices in AI from a rural childhood in Lancashire to one of the world’s most prestigious universities.

Deasey-Weinstein was recently awarded a coveted place at the University of Oxford’s Saïd Business School. She will study for an executive diploma in artificial intelligence for business, supported by the executive diploma scholarship for women. It is an achievement that situates her in an elite network of executives who are not only fluent in technology, but also tasked with shaping how AI transforms societies.

“This represents not only a personal achievement but also validation of the Cayman Islands’ growing presence in the global AI and technology landscape,” she said.

The road to Oxford

Deasey-Weinstein’s path to Oxford has been far from linear.

After studying public relations and marketing at the University of Central Lancashire and completing a master’s in educational leadership at the University of Manchester, her career included stops in crisis communications, business development, writing, consulting and counseling.

“I’ve always worked in data-driven roles, and I’m fascinated by people; how we think and why we decide what we do,” she said. “That ran through every job I chose in life – psychology modules as an undergraduate, marketing work analysing customer behaviour, communications roles understanding audiences, and now using data to predict, analyse and build tools that improve lives.”

The turning point came in 2023, when she was selected to join MIT’s Professional Certificate in AI and Machine Learning, a programme with just 80 participants from over 40 countries.

“The ‘this is it’ moment for me was seeing real outcomes, people saving not just hours but lives,” she said of her immersive experience at MIT. “That’s when I committed to making AI understandable and useful for everyone, not just specialists.”

Her rise has been swift. She has been published in pieces on AI’s disruptive potential in Forbes and The Round Table Journal, has been appeared on BBC World Service and earned LinkedIn recognition as a top AI thinker. Locally, she serves on the Cayman Islands AI Society Steering Committee and the Chamber of Commerce Council and has won multiple fellowships for her ongoing work in AI innovation in the educational system in Cayman.

Yet at home, her proudest audience is her family. “We often study side by side,” she said. “Learning never stops.” Diana Weinstein, her spouse – also studying for an MBA – is “the quiet force holding the centre”.

The road ahead

Deasey-Weinstein is clear about her mission: to use her Oxford experience to bring back knowledge and networks that improve life in Cayman. She knows some are fearful of AI, but argues Cayman should shape the technology on its own terms.

Her work bridges technical insight with policy and education – two areas she sees as critical for small, ambitious economies like Cayman.

“We’re small enough to move quickly, close enough to decision-makers to turn dreams into reality and globally connected enough to bring the best ideas home,” she said.

At Oxford, she plans to leverage access to a global network of leaders to benefit Cayman’s business and policy landscape. The goal, she says, is not a “trophy on a shelf”, but the ability to bring back frameworks, partnerships and real-world pilots to strengthen Cayman’s economic resilience.

PwC has projected that AI could add 15% to global GDP by 2035. Deasey-Weinstein wants Cayman to capture its share.

“Oxford isn’t just about me,” she said. “It’s about Cayman being at the table as these technologies reshape the global economy.”

For now, she is getting ready to head off to Oxford in a few months. Her first of four immersive modules begins in January after which she will conclude the programme remotely.

Her message to young Caymanians, especially girls, is simple: Don’t wait.

“Cayman’s young people don’t need to wait for opportunity as it’s already on our doorstep,” she said, reflecting on her path from Lancashire to becoming a national AI voice in Cayman while raising a family and still telling bedtime stories.

“You belong in these rooms. Not ‘one day’, but now,” she said. “You do not need to be a programmer or a coder. Pick one tool. Use it. Ask for feedback. Repeat. Use our island’s superpower. Access. Bring all of you. Your creativity, your innovation, your grit, your lived experience. AI isn’t just maths; it is music, language, community, creativity, empathy. Just have the courage to step out of your comfort zone.”