Ben Bailey


Ben initially joined the SteppingStones team back in 2018 before heading back to the UK in late 2019. After a successful stint back in England, he rejoined the team in July 2021 as a Recruiter specializing in Technology whilst still supporting the rest of the team with vacancies across several industries.

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.

Outside of work, Ben enjoys playing a variety of sports including Tennis and Football. When he isn’t exercising, you can find him eating/drinking in one of the many restaurants (mainly Casanova!) or topping up his tan on the beach


Don’t believe us?
Believe them.

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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