Enterprise Cayman

Pathways In Tech

The Enterprise Cayman Pathways in Tech Programme is designed to support Caymanian learners in pursuing high-demand careers within the digital economy. Each pathway offers a structured certification progression — from foundational to advanced levels — aligned with industry standards and employer expectations. Whether participants are looking to enter the workforce, switch careers, or advance their current roles, these curated learning tracks provide the technical skills, credentials, and practical knowledge needed to thrive in today’s technology-driven landscape.

Facilitated by:Dion Training LOGO (1)-1

 

Why take part?

Learn Together, Grow Together

Progress through your pathway alongside peers, supported by shared group chats and a dedicated point of contact at our Launch Labs Studios space. With CyberSandbox sessions, networking opportunities, and employer mixers hosted, you’ll stay connected, accountable, and inspired while building meaningful relationships along the way.

Connect with Industry Mentors

Tap into Enterprise Cayman’s network of industry-aligned mentors who bring real-world expertise to your pathway. Mentor meetups provide personalised guidance, career insights, and practical advice - giving you a direct connection to professionals who’ve successfully navigated the tech industry.

Train with Hands-On Experience

Learn through exclusive Cybersandbox workshops and labs designed to simulate real-world challenges and tools. Whether you’re building cloud-secure networks, troubleshooting IT issues, or running Agile sprints, you’ll be gaining skills you can apply immediately on the job.

Collaborate & Study Together

Tap into the collaborative environment of Launch Labs Studios. Weekly or biweekly study groups, hosted both online and in the space, keep you accountable and supported. You’ll have a hub for problem-solving and staying on track.

Grow Your Career Toolkit

Polish your professional profile with CV and LinkedIn workshops, pathway-specific mock interviews, and support building a standout digital portfolio. Gain access to invite-only networking mixers with industry professionals, and CEC zone clients.

 

Stay Connected

Launch Labs Studios ensures your connection doesn’t end with the pathway. As part of this vibrant community, you’ll continue to access events, opportunities, and networks that evolve with you — supporting your career long after the programme finishes.

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Project Management Specialist

 

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This pathway is designed to build project management expertise from the ground up, starting with foundational principles and progressing to globally recognized certifications. Participants begin with an introductory CompTIA Project course, advance to the industry-leading PMI PMP certification, and can optionally pursue Agile-focused training with the Professional Scrum Master (PSM). Career opportunities include roles such as Project Coordinator, Project Manager, Program Manager, Scrum Master, and Agile Delivery Lead.

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Computer Support Specialist

 

ITIL LOGO

CompTIA A+ LOGO updatedCompTIA Network LOGO updatedCompTIA Security LOGO updated

 

 

This pathway prepares individuals for careers in IT support and help desk operations, building essential skills in service management, hardware troubleshooting, networking, and cybersecurity. Starting with foundational certifications in IT support and networking, learners progress to intermediate-level security training — equipping them to manage incidents, maintain SLAs, and protect systems against common threats. Career opportunities include positions such as IT Support Specialist, Help Desk Technician, Network Administrator, Systems Support Engineer, and Cybersecurity Analyst.

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Network Systems Administrator / Architect

 

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Cisco CCNA LOGOCompTIA Security LOGO updatedAWS Solution Architect LOGO

 

 

This pathway builds the skills needed to design, manage, and secure enterprise-level networks — both on-premise and in the cloud. Learners start with core networking concepts and progress through Cisco configuration, cybersecurity, and advanced cloud architecture with AWS. Career opportunities include positions such as Network Administrator, Systems Engineer, Cloud Architect, Network Security Specialist, and Infrastructure Manager.

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Pathway Related Events

Each pathway is supported by Cybersandbox labs, study groups, and networking opportunities, scheduled around your learning so you can apply skills, prepare for certification, and grow your network.

More pathway-related events coming soon..

*Priority access for enrolled participants.

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Who can register for the pathways?

Enterprise Cayman welcomes all individuals of 18+ to take part and register! This includes adults looking for a career change, IT professionals seeking certifications or growth and development, and university/college learners.

When does registration open?

 

Registration opens every 2–3 months during our flexible intake windows. This allows you to join when it best fits your schedule, rather than committing to a fixed cohort start date.

Is there any need-based assistance available?

Yes, we offer limited need-based assistance for Caymanians. To ensure fairness, applications are reviewed after you’ve registered your interest and reviewed the course fee. If the fee is the only barrier, you can request need-based assistance, and our team will reach out. Awards typically cover part of the course fee and depend on available funding.

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Are the courses in-person or online?

The certificate courses are delivered online - designed to be both flexible and self-paced, allowing participants to learn at their own speed while receiving the guidance they need to succeed.

If your course includes an exam voucher, you will get an exam voucher that is based on your location to ensure you can take the exam in your local area or online.

Will I need a specific platform for the self-paced courses?

The pathways do not need any special software, and simply a web browser.

Is there a deadline to complete the self-paced courses?

Learners are given a period of 12 months to complete each certificate.

Will I be provided a certificate upon completion of a course?

Yes, Dion Training issues a digital badge upon successful completion of each course that is completed. They are an accredited training organization for ITIL®, PRINCE2®, and PRINCE2 Agile® and also a Platinum Partner for CompTIA certification exams. These certificates require multiple courses and are recognised around the world.

Questions?

If you have any other questions, please email us at innovate@enterprisecayman.ky.

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