Enterprise Cayman Launches New Training Pathways to Equip Caymanians for Tech Sector Career Opportunities and Advancement

Cayman Enterprise City’s Enterprise Cayman initiative has announced the launch of its new Pathways in Tech programme, which is designed to provide Caymanians and residents with the in-demand skills, knowledge, and industry certifications needed to thrive in today’s rapidly evolving digital economy.

Registration is now open for the Fall 2025 cohort, with access to the online courses becoming available on 1 September 2025. Participants can choose from three high-demand career pathways – Project Management Specialist, Computer Support Specialist, and Network Systems Administrator/Architect, with each pathway offering a series of globally recognised certifications. The programmes are self-paced with flexible intake periods and require no prior experience, making them ideal for everyone from school leavers to mid-career professionals seeking to pivot into tech.

“Our goal is to create clear, accessible pathways into career opportunities that are available today. This programme is designed for Caymanians preparing to enter the workforce, as well as those already in the workforce who are seeking to upskill or make career changes,” said Charlie Kirkconnell, CEO of Cayman Enterprise City and Chairman of Enterprise Cayman. “With the launch of these pathways, we’re making it easier than ever for Caymanians to build in-demand skills, immerse themselves in a vibrant technology focused ecosystem, and connect locally with global opportunities in the digital economy.”

The Three Career Pathways Include:

• Project Management Specialist (CI $684) - Certifications include CompTIA Project+, PMI PMP, and optional Agile-focused PSM certification. Ideal for those pursuing leadership roles in operations, project delivery, or strategic planning.
• Computer Support Specialist (CI $1555) - Certifications include Axelos ITIL Foundation, CompTIA A+, CompTIA Network+, and CompTIA Security+ certifications. Prepares participants for careers in IT support, troubleshooting, and systems maintenance.
• Network Systems Administrator / Architect (CI $739) - Certifications include CompTIA Network+, CompTIA Security+, Cisco CCNA, and AWS Solutions Architect certifications. Equips learners with skills to design, implement, and manage secure, scalable networks.

All pathways are delivered in partnership with Dion Training, offering a streamlined enrolment process and hands-on learning resources.

While the programme is self-paced and delivered online, Enterprise Cayman will also host a series of networking events throughout the programme period. These include CyberSandbox workshops and interactive sessions designed to connect participants with peers, subject matter experts, mentors, internship opportunities, and potential employers, ensuring that learning goes hand-in-hand with building valuable professional networks.

“The Pathways in Tech programme goes beyond certificates - it’s about equipping people with the skills, confidence, and connections to take charge of their careers,” said Alyssa Manderson, Programme Manager at Enterprise Cayman. “We’ve designed these pathways to be flexible, supportive, and directly aligned with what employers are looking for right now. Whether you’re stepping into a new field or aiming for your next big move, this is your opportunity to invest in yourself and move forward with purpose.”

Registration is now open. To learn more and enrol visit https://www.enterprisecayman.ky/pathways or contact innovate@enterprisecayman.ky. Flexible payment plans and needs-based scholarships are available upon request, ensuring that anyone can take the first step toward a future in tech.