Cayman has a very strong temporary and contract staff market for both short-term and long-term assignments, especially in the legal and financial markets. We are committed to staying ahead of the growing requirement for temporary staff and the latest employment opportunities, enabling us to exceed the expectations of our clients, provide consistent employment for our contract staff, and create new opportunities for Caymanians to secure a career change.

Since the launch of SteppingStones in 2005, our focus has been to build trust and competency by nurturing business relationships. We are sympathetic to clients recruiting for a new role and ensure that we match high-calibre candidates to positions through our careful selection process.

SteppingStones services include taking care of all your immigration requirements, managing the entire process from beginning to end. With 30+ years combined immigration consultancy experience and an excellent relationship with the Cayman Islands Government Immigration Department, we are able to keep abreast of the ever-changing laws, policies, directives and procedures of the Department of Immigration, The Work Permit Board, The Trade and Business Licensing Board and The Business Staffing Plan Board.

Outsourcing payroll and benefits administration gives our clients access to our unrivalled HR knowledge and expertise, ensures compliance with The Cayman Islands Labor Law, and significantly reduces the time, resource and financial costs involved with in-house operations. Our wide range of services include full payroll and benefits administration, corporate accounting services and strata account management.

Investors In People Gold Accreditation

In January 2016, SteppingStones was awarded the Investors In People Gold (IIP) Accreditation.

The award is a source of great pride to our company, and shows our dedication to creating the best possible environment for employees so that we in turn can provide the highest level of service to our clients.

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Recent Jobs

The latest job opportunities are listed below, or search our entire database using the search filters.
For the highly-qualified, motivated and career-driven Accountants with Captives experience, we want to
Due to an increase in demand, we are actively recruiting for qualified accountants to fill various contracted
Are you a highly-motivated, driven and detail-orientated Company Secretary who has a proven track in
Now that you have gained several years of legal experience working in reputable law firms, you're wondering
Have you ever considered a move to sunnier climates, specifically one in an offshore jurisdiction where
Our client is looking for an organized project manager to join their qualified team. Duties will include; -

Some of the companies we've helped recruit excellent applicants for over the years.


Click any questions to reveal the answer.
What sort of salary can I expect to earn?

Salary is wholly dependent on qualifications and experience and the role that you fill. Our experienced recruiters will be able to give you expert advice but to give an idea, professionally qualified contract staff can expect to achieve an hourly rate of US $30.00 per hour. Professional accounting and finance staff can expect to earn an annual salary of between US$55,000 to US$85,000 and above subject to number of years post-qualification experience.

Can my partner also work in the Cayman Islands?

SteppingStones has a very diverse and interesting client base and no matter what work experience your partner has it is very likely that we can assist them in securing a position. We would suggest their CV be forwarded to us at the same time as yours.

Where does SteppingStones recruit its applicants from?

Alongside Cayman, SteppingStones successfully recruits individuals from all over the world, with strong connections in the United Kingdom, Ireland, South Africa, Australia, New Zealand, Canada, USA, Zimbabwe, Zambia, Barbados, Trinidad and many other Caribbean and international locations.

How soon can I start and how long can it take for me to start work once I have been offered a position?

If you are a Caymanian or on-island based candidate we can commence the search for your new dream job today. If you are an expatriate worker you will be required by law to have a work permit. It can take from 48 hours to three months for a work permit to be processed and approved depending on the type of work permit applied for. Where a work permit is required we strongly encourage individuals not to tender their resignation from their current position until they are advised their work permit has been approved. Work permits can be activated on the day you arrive on island, rather than the date they are approved.

How do I travel to the Cayman Islands?

The Cayman Islands are located South of Cuba and West of Jamaica. Cayman Airways and various American airlines fly direct from Miami and numerous other US cities including Atlanta, Houston, Tampa, Orlando, Fort Lauderdale, New York, Boston and Chicago (some seasonal). British Airways flies direct from London via the Bahamas to Grand Cayman, and Air Canada and West Jet fly direct from Toronto. There are frequent direct flights from Jamaica and many direct charter flights from Mexico, Costa Rica, Dominican Republic, Cuba, etc.

Do SteppingStones' contract staff always have employment?

Contracting in the Cayman Islands is very like contracting anywhere. Whilst we cannot guarantee you will work every day of your contract with us, if you are a skilled individual who is flexible, ambitious, outgoing and enthusiastic it is likely that you will be kept fully engaged.

What's the dress code on Island?

With the weather ranging from hot to hotter you might think the dress code is shorts and sandals. However, with air-conditioning used in almost all shops, hotels and businesses, the dress code for work is shirt, tie and trousers or suits for the guys and shirts/blouses, skirts/trousers or suits and closed toe shoes for the girls.

Resources & News

Local and industry news, expert tips and tricks and articles of interest from the team at SteppingStones.
Wed, 19 October 2016
The word “confidentiality” has both casual and legal meanings in t...
Wed, 12 October 2016
Calling allSteppingStones Fans to “Like” and share our Stepp...
Mon, 10 October 2016
Happy Thanksgiving to all of our fellow Canadians! Here are some f...