IT and Tech Recruitment for Candidates

Cayman IT and Tech Recruitment | Stepping Stones Recruitment

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. 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


As the Cayman Islands become more and more technology-focused, Ben is very well-placed to assist clients and candidates with a wide variety of requirements. Ben has already started to establish himself as the go-to Tech Recruiter in the Cayman Islands and is already working with a very impressive portfolio of companies on-island.


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SteppingStones has been handling all or our recruitment needs and most of our training needs since Milly established the company. We have been delighted with the quality of service that they provide and with the quality of staff that they have managed to recruit for us. Fidelity is a growing company it is vital that we continue to attract and retain the best staff possible. Our partnership with SteppingStones is integral to our plan for achieving this objective .

– Brett Hill

We have been working with SteppingStones since its inception and have always been impressed with the calibre of the secretarial staff available for temporary assignments. As the largest law firm on the island, our need for experienced legal secretarial support staff is constant. Milly and Ciara have taken the time to get know and understand our practice, as well as the culture of Maples, so that the secretaries from SteppingStones are a good “fit”, based on their skills and personalities. A high percentage of SteppingStones’ temporary staff members stay on to fill vacancies for permanent positions within the Firm.

– Morven Bodden

SteppingStones is a first class company that provided us with amazing personal service and a fully comprehensive training course. I will definitely recommend then to anyone and we will continue to use them in the future.

– Jeremy Ebanks

We greatly appreciate your generosity in taking into account our charitable status. You will be pleased to hear that your temp seems to be settling in well and we are pleased to have her with us. It is nice to have such a cheery personality in our midst. Once again thank you very much.

– Pat Bain

Thanks very much for all of the help Pam! The service in processing a temporary work permit has been excellent.

– Richard Reading
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IT Recruitment for Candidates

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