Cayman Reinsurance Jobs

SteppingStones is the leading recruitment agency for the Cayman Islands’ reinsurance industry.


Specializing in the actuarial, finance, and compliance functions for both the P&C and Life & Annuity space, we connect firms with exceptional candidates. SteppingStones combines its unrivaled understanding of the Cayman Islands job market with intricate knowledge of the reinsurance industry to identify and attract the best fit for your company. Partnering with our reinsurance recruitment specialists means unlocking access to top industry professionals with experience navigating the world of offshore reinsurance.

Whether you’ve been on-island as long as we have (collectively over 50 years!) or are new to our white sandy shores, our recruitment solutions will provide you with the competitive advantage to thrive in the Cayman Islands’ dynamic landscape. Are you in search of an ultra-specialized pricing actuary with exposure to specific products, systems, or capital frameworks? Or a compliance professional that can navigate the unique requirements of the jurisdiction? In any case, we go beyond the bullet points on candidates’ resumes to understand their ability to thrive in this unique environment.

Besides the flexible and robust business climate, the Cayman Islands is emerging as a reinsurance hotbed due to its access to a talented workforce; that’s where we come in! As the global demand for reinsurance continues to grow, no firm is better suited to finding you the people to help you grow with it.

Please reach out to Kiera for your initial consultation

Charlotte Morrish

Kiera Hannula

Senior Recruiter

Kiera relocated from Chicago to Cayman in 2021 to join the SteppingStones’ team as a Senior Recruiter, bringing with her extensive experience in pairing top-performing and rising professionals with their next career move. She holds a Bachelor’s degree from the University of Minnesota Duluth and a Masters in Human Resource Management from Saint Mary’s University of Minnesota.


Don’t believe us?
Believe them.

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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Reinsurance Recruitment

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