IT and Tech Recruitment for Candidates

The Technology industry in the Cayman Islands is one of the most progressive sectors on-island, attracting several fast-growing tech firms from all over the world.


Cayman IT and Tech Recruitment | Stepping Stones Recruitment

Additionally, established companies in Cayman across many sectors are continuously looking to bolster their technology teams as the island becomes more and more modernized. Emerging technologies are very present in Cayman and several organizations look to hire top talent internationally to keep up to date.

Our clients have a constant need for specialists across several areas of technology. Our more common vacancies include Service Desk, Software Development, Quality Assurance, Cyber Security, Business/Data Analysis, IT Project Management, IT Sales and plenty more.

The introduction of Cayman Enterprise City has developed a community of innovative companies which has grown into an entrepreneurial tech hub, home to some of the fasting growing Tech/FinTech companies. These businesses range from start-ups to mid-sized enterprises as well as larger corporate organizations who are looking to develop a presence in Cayman.

Gaining global exposure in Cayman has been proven to open several doors for tech professionals. Many of our clients in Cayman have offices in various other jurisdictions and off-shore experience is now highly sought after.

SteppingStones is the leading Recruitment Partner in the Cayman Islands and due to our reputation that has been built over many years, we are fortunate to work with a huge variety of organizations on-island across several sectors, doing our best to give both local and international candidates the best chance of securing a new opportunity. We are massively motivated to continue seeing a clear increase in local Caymanian talent in the tech space, supporting Graduates looking for their first role to experienced local professionals looking to progress within the world of technology.

As the Tech industry in Cayman becomes more and more buoyant, we are always eager to chat with tech professionals regardless of specific expertise – to advise on the job market in Cayman and your suitability for any current and future opportunities you may be interested in. SteppingStones are known for their honest and transparent recruitment process, offering a professional and personable service.

For more information and a private/confidential chat, please contact Ben Bailey at or call on 345-326-2059.


Ben Bailey

Senior Recruiter

Ben has extensive years’ of global recruitment experience with the majority of those years focused on roles in the Cayman Islands. Ben is the go-to Tech Recruiter in Cayman and successfully launched SteppingStones Tech in 2022, providing a tailored service to clients and candidates on-island.


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I would like to start off by saying that it has being an absolute pleasure working with SteppingStones and how lucky I was to have Ms. Luisa on my side through the entire process. I was seeking for a new job opportunity as I was not pleased with the organization I was working for at the time. Ms. Luisa quickly reached out to me and offered a new job vacancy for which we both agreed that it was a perfect fit for me. Before and after my job interviews, Ms. Luisa made it her priority to contact me via telephone and email in order to ensure that I was prepared, had a positive mind set, confident within myself and ready to begin this new journey. I must say, SteppingStones made this journey extremely easy for me and I was able to transition with an open mind. Would I do it again? Absolutely! I highly recommend SteppingStones to all of you who seeking a new career opportunity.

Ben is a phenomenal Tech recruiter and highly recommend him. He removed the stress and complexity, in what was for myself, a very important career decision within a very tight market. Ben was consistently professional, timely, and respectful in all interactions. I am writing this because I am very happy with the outcome, and Ben’s ability to deliver results.

The service I received was exceptional. I really enjoyed working with Charlotte – she was super responsive and easy to get hold of. She always provided honest, sensible advice and I never felt like I was being pressured.

The service I received from SteppingStones was exceptional, particularly the turnaround time and Rosie’s responsiveness, commitment, transparency and positivity. There was absolutely nothing that disappointed me during the recruitment process and I would recommend SteppingStones to my family and friends!

I would definitely recommend SteppingStones. Rosie had a genuine interest in my placement and she continued to be contactable and responsive post-placement, which really stood out to me. Overall I received a very good service which was professional and genuine. Thank you!

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IT Recruitment for Candidates

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