Chief Technology Officer

We are a newly established boutique law firm in the Cayman Islands, focused on complex commercial litigation and insolvency matters within the financial services sector. Eldridge Legal LLP is founded by a team of prominent marketing leading experts and former members of the litigation team of the world’s largest offshore law firm. We are building a top-tier boutique firm: focused, nimble, highly selective, and uncompromising on quality. The Role We are seeking a Chief Technology Officer who is both a hands-on builder and an executive technology leader. The successful candidate will help shape our technical strategy and will lead the development and delivery of our platforms across web, mobile and AI, working with the team to implement and continuously improve our systems. The CTO will convert ideas into shipped, measurable outcomes, build secure solutions, and develop litigation-focused workflows and tools into scalable, high-impact capabilities for the firm. What We Are Looking For

• Technical founder/CTO experience with track record shipping production software and building complex applications.
• Proven leadership of cross functional, distributed engineering delivering for enterprise grade clients and multiple stakeholders.
• Extensive experience with AI/LLM and retrieval augmented systems; ability to index internal knowledge and enable plain language querying.
• Strong background in secure, automated operational pipelines.
• Excellent communicator able to explain complex technical concepts to non engineers.
• Formal training or a qualification in risk management is a plus.

Duties

• Define and execute technology strategy, architecture and roadmap across stack and infrastructure; establish delivery governance and standards.
• Deliver AI enabled firm intelligence, knowledge indexing and actionable insights for litigation and operations.
• Design secure, automated workflows for onboarding, disclosure and compliance; enforce risk controls and resilience.

What We Offer The role offers a salary range of USD250,000-300,000, comprehensive health insurance, five weeks’ annual leave, and statutory pension benefits. Location and hours The role will be based in George Town and is a full-time role (8.30am to 5pm). Interested Caymanians and legal residents should send their CV with a covering letter to rachel.nyman@eldridge-legal.com.