What judging the 2026 CIMPA Awards taught me about good marketing

This year I was asked to judge the CIMPA Awards (Cayman Islands Marketing Professionals Association). I said yes before I’d finished reading the email!

CIMPA is the Cayman Islands Marketing Professionals Association. Every year it gathers the best work the island’s marketers, agencies and brands have produced and puts it in front of a judging panel. The 2026 awards ran alongside the CIMPA conference on 17 and 18 April at Hotel Indigo in Grand Cayman, under the theme “Level Up: Marketing’s New Formula”. The gala closed the weekend on the 18th. Nine categories, and some genuinely close calls.

My first lesson

Judging is way harder than it looks! You can’t reward a clever idea that went nowhere, equally, you can’t ignore the ‘less creative’ work that delivered results. Also, trying to remove personal taste from the equation is a tough discipline to master!

A few things really stood out.

You could spot the strong ones a mile off. They knew exactly what they were solving before they went anywhere near the creative, who they were talking to and what they actually wanted audiences to do. They were able to evidence results and impact.

That said, ‘results’ meant something completely different from one entry to the next. Some entries were measuring turnover, others sales, and others a real shift in how people behaved. Health City’s “Mind the Gap” work, which won Community Impact, was very much that last one. All of it brilliant, honestly. And that’s what made it such a good, yet tough one to judge: how do you weigh up whose impact matters most, turnover against a real change in behaviour?

The range was impressive too! Compass Media won Campaign of the Year for TimeBack. AirVu Media took Agency of the Year. The Cayman Islands Government’s GOV.KY won Website/App of the Year. The Ritz-Carlton, Grand Cayman’s Giro de Cayman took Video of the Year. Rebekah Brooks was named Marketer of the Year, Rosita Ritch the Rising Star, and Robert Tyler Creative Professional of the Year.

My pics

Right, personal taste back in! Two stood out for sheer creativity, and they were poles apart. Giro de Cayman by the Ritz-Carlton, Grand Cayman leaned right into humour, playfulness and drew you into the light-hearted story. The Aurora Life commercial by Armada Films went the other way entirely. Cinematic, aspirational, full-on standing-on-a-mountaintop stuff. Both stunning, both very different!

AI

AI came up too, of course it did… it was one of the big threads this year. And a fair few entries had used it somewhere in the process, not to do the whole job. What I really respected was that nobody tried to hide it. Where teams had leaned on AI, they told us, and they were clear about where it helped and where the thinking and the creative calls were theirs.

So much talent on one small island! 🏝️

The Cayman Islands is a small market. The work isn’t small at all!

Thank you to CIMPA for having me, and to everyone who entered. Putting your work up to be judged takes nerve, and it was a real privilege to read it.

If you’d like a second opinion on your own marketing, with the same eye I brought to the judging table, that’s exactly what we do at Love & Logic. Get in touch and let’s have a chat.