Leonard Lewis

I spent the last decade building marketing technology platforms inside regulated enterprises: banks, law firms, jurisdictions where mistakes cost real money. Now I build AI-powered tools for businesses and teams of all sizes through Caydev, a product studio I started in the Cayman Islands.

My career started in banking infrastructure at HSBC, managing core systems, servers, and enterprise applications. I moved into marketing technology at Walkers, an international law firm, and spent the next decade scaling the function from the ground up. What started as campaign support became a global Martech operation across ten jurisdictions, with a team of direct reports, vendors, and consultants. Along the way I delivered a six-figure Sitecore enterprise rebuild and led platform investments totalling multiple millions across the portfolio. I also helped drive the firm's move into AI, from building the business case to selecting tools and running pilots. I hold an Honours B.A.Sc. in Computer Engineering from York University.

In parallel, I founded Caydev in 2013 to build impactful platforms that would benefit the local community. Running both tracks taught me something useful: I can architect and manage enterprise-level platforms and systems, and still ship a side project in a weekend. Day to day, that means I move between Martech strategy, platform architecture, and hands-on development with the latest toolkits and frameworks, with the vendor and budget management in between.

Going forward, my focus is AI-native products and platforms. I want to take everything I've learned from corporate systems and processes, marketing strategy, and engineering and channel it into building tools that solve real problems. The playbook is the same one I've run for a decade: understand the domain, ship fast, measure what matters. The difference now is the tools are smarter, and so is the ambition.

Read what I'm working on >>