Hunted Worldwide: Cayman Islands

Welcome back to Hunted Worldwide. This week, we’re off to the heart of the Caribbean. And leaving a towel on the sun lounger for you is a brand new Hunted partner.

The Agency is a full-service boutique recruitment consultancy providing permanent, temporary and executive search services to companies based on the island. The Cayman Islands is a global financial hub and The Agency focuses on mid-senior level positions in both the financial services and legal space.

The company Founders partnered together from competing agencies, both of which are still active on the island. I spoke to Chelsea Flynn, Co-Founder and Recruitment Manager of The Agency, to find out what makes recruitment tick in Cayman.

1) Market Overview

The Cayman Islands has long been seen as one of the world’s premier global financial hubs, boasting a client-centric market in prominent financial sectors like banking, audit and hedge funds. HSBC, PwC, Scotiabank, Ernst and Young, and Deloitte are just a few names that have made their home here.

As an offshore tax-neutral jurisdiction, Cayman imposes no personal income tax, local corporate tax or sales tax.

Cayman’s also home to many of the world’s top professionals in the areas of law, accountancy, corporate services and investment expertise. Essentially, it’s very much a candidate-driven market:

“You could pull twenty jobs in one morning. And if you build up a good reputation with your clients and candidates, filling jobs isn’t a problem. The supply of good talent is limited in comparison to the demand so having solid networking skills is key on the island”

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2) Contract Vs Perm

The short answer’s the split’s about 70/30 in favour of perm. But it’s important to note the role immigration plays in contract recruitment.

Wherever possible, employers will try and source local Caymanian talent to fill positions. If that’s not possible, they’ll consider work permit holders based on the island. And failing that will bring talent in from overseas.

“Once you do identify a winner of a candidate, it’s never a tough sell as clients appreciate that good talent is hard to find so they will move quickly to make an offer”

We’ll cover work permits in more detail towards the end of this article but for contract, agencies apply for permits on behalf of candidates and assign them to their client. So candidates are employed by the agency for the duration of their assignment.

3) Professional Community

The size of the population in Cayman lends itself nicely to networking. It’s a friendly, laid back island where the professional community comes together quite organically. Locals prefer meeting face to face for coffee, lunch or Happy Hour drinks.

There are big conferences throughout the year, business functions at the major hotels, and a community focus on supporting local charities.

cayman cafe

4) Business Culture

The key thing to remember is that even though it’s sunshine and lollipops on the island, it’s not somewhere you can pitch up to work in an open shirt and flip flops and expect to do well. You’ll have to work hard to get ahead in Cayman.

It’s less cut-throat than say London tech recruitment but just as busy. Although this is offset by lucrative tax-free earning potential.

5) Language

The island’s a real melting pot, with over 135 nationalities calling Cayman home. That said, everyone on the island speaks English.

6) Business Development

BD’s not desperately process-driven in Cayman. Although a lot of the work you do will go through HR. But don’t turn your nose up at that just yet.

HR aren’t the blockers to business they’re rumoured to be in other parts of the world. Here, they’re on your side and are supportive of recruitment agencies in Cayman.

The Cayman Islands HR Society hosts a big annual event each year. The Agency enrol all their team for this, so it’s a superb place to network.

cayman docks

7) The CBD

George Town’s the capital of Cayman. And that’s where you’ll find The Agency’s brand new office, as well as all your major law firms and investment banks.

Cayman Resident is a brilliant online resource for anyone weighing up a move to the island. And this article on George Town should give you a pretty decent snapshot of life in the capital.

8) Dress

First of all, it’s consistently boiling in the Caribbean. We’re talking 25° at night and 30° during the day.

During the week, Recruiters are in smart-casual. The Agency operates a ‘dress for your day’ policy. Pretty much the whole island does dress-down Fridays.

And you’ll be pleased to know that all offices and homes are air conditioned.

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9) Travel

Small islands generally aren’t the best for public transport. Uber hasn’t made it there just yet. Buses run but are known to operate on their own schedule. Taxis are expensive and it’s generally too hot to ride bikes.

Most people get a car as one of the first things they do once they make it to the island. In fact, The Agency provide a rental for anyone arriving in Cayman for the first time while they get situated. For that, ecayTrade is the Cayman equivalent to Auto Trader.

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Life In The City:

1) Weather

The island doesn’t experience four seasons throughout the year. It’s either summer or rainy season. But it’s hot all year round.

The rain comes between September and December, where it’s cooler with a bit of a breeze. A bit like an English summer. And when it does rain, it’s over in a matter of minutes.

Every Caribbean island has a solid infrastructure to protect against hurricanes. Cayman haven’t had one in years but you’d want to be prepped if you ever moved there. So here are some tips.

2) Housing

Most people who aren’t from the island, rent. ecayTrade also does rentals for housing as well as cars, so is well worth a look. You’ll invariably go through a real estate agent, of which there are plenty on the island, and will need rent and deposit in advance, same as you would elsewhere.

It’s reasonably easy to buy. And refreshingly, your commission and bonus will be taken into account alongside your (relatively high) base salary.

cayman food

3) Food

“Cayman’s a foodie’s dream!”

Naturally, there’s a big emphasis on fresh seafood. Mahi mahi is a specialty. And both lobster and conch get their own seasons throughout the year.

Chelsea tells me the fish tacos at Cabana in George Town are the best on the island.

4) Outdoor Space

Put it this way, Cayman’s not exactly difficult to look at. The island’s built up similar to nearby Miami, and the views are absolutely stunning.

You’ve got Seven Mile Beach, which is exactly as the name implies: a massive stretch of white sands and bright blue ocean. There’s Stingray City, where you’ll head out on a boat and get to swim with the rays. And Starfish Point, a quiet patch of sand near the sea with plenty of five pointed pals to hang out with.

cayman on the water

5) Social Scene

Funnily enough, most socialising’s done outdoors. And there’s absolutely tonnes to do. Plenty of watersports: stand-up paddle boarding, jet skiing, water skiing, kite surfing and parasailing are all quite common.

You should probably get a boat. They’re about the same price as a car and you won’t need a licence to take to the water.

For those fond of dry land, you’ll be pleased to know that brunches are a big one. And if you need to work off four hours of non-stop champagne on a Sunday, there’s plenty of gyms and a massive yoga scene. CrossFit’s big in Cayman too.

It’s a Christian island, so while everything’s open until 4am on Friday, the bars shut just after midnight on Saturday. And it’s an important reminder that while you’re in literal paradise, a 24-hour party island Cayman is not.

6) Family

Schools for expat kids have to be paid for out of pocket. And most families employ a nanny or helper to work with them during the day. There’s lots of soft play areas and kids camps to take advantage of.

Not to mention the glorious beaches.

cayman beach boat

7) Cost Of Living

When you factor in how much you’ll earn living and working in Cayman, it’s about comparable to London. And employers make sure you earn enough to live comfortably. Mainly because people in Cayman are really nice. But also because they’ll want you to stay once you’re there.

The Agency will put you in touch with real estate agents and find that most people spring for either a 2-bed at around $1,800 KYD or a 1-bed apartment for $1,000 a month. For reference, $1 KYD is equivalent to about 92 pence.

8) Tax

Arguably one of the strongest draws to setting up shop and establishing yourself on the island is the fact that Cayman’s a tax neutral jurisdiction. This means there’s no direct tax to your income. The only deductions you’ll see are for health insurance, which everyone in Cayman’s required to have by law.

The only other deduction’s pension contributions, which don’t kick in until you’ve been on the island 9 months and set up a pension plan:

“Legally, you have to contribute 5% of your earnings to a pension plan and your employer will match that contribution up to 5%. If you leave the island, your pension contributions can be transferred to a pension plan overseas”

cayman hammock

9) Work permits

Anyone not from the Cayman Islands will need a permit to work here. The employer issues the paperwork on the candidate’s behalf and covers the cost of it. As long as there are no suitably qualified Caymanians available for the position, the permit’s typically granted.

If you have a criminal record, you won’t be able to secure a police clearance certificate – vital when filing for a work permit.

“The work permit process can vary depending on the type of permit the employer applies for. But for a permanent role, typically it takes between 6-8 weeks for it to be approved. Express temporary 6 month work permits can be approved as quickly as 48-72 hours”

The Agency have an immigration specialist to assist with this.

10) International Travel

Miami’s only an hour and a $100 flight away. You’re an hour from Jamaica, Cuba, Panama. And all flights are direct through Cayman Airways.

Direct flights also go to New York, Chicago and Denver, although there’s only a handful a day. You’ll find a flight schedule for Summer 2019 – good from now until November – here.


At the time of writing, The Agency’s looking for two Senior Recruiters to work out of their brand new office in George Town. They’ll even help you move. Check out The Agency on Hunted and pop them an anonymous message if sun, sea and a tax-free lifestyle sounds like your thing.

A huge thank you to Chelsea for her time and insight in putting this piece together.