Cayman Islands (KY)
US$180,000 - US$220,000 (TAX-FREE)
02 Dec 2023
30 Dec 2023
Full Time
7+ Years
Experience Level
Senior Level

A vacancy has arisen at this major global offshore firm for a high quality FS regulatory lawyer with at least 6 years' post-qualification experience from an international law firm. You must be admitted in either the UK, Australia, New Zealand or Canada and have a keen desire to develop your career offshore.

The role will involve advising on a broad range of non-contentious regulatory matters for various industry sector clients including economic substance, beneficial ownership, anti-money laundering, sanctions, licensing and registration, FATCA/CRS, and regulatory obligations applicable to investment funds, as well as contentious regulatory matters including investigations and enforcement actions. You will have a deep understanding of the financial services industry overall including banking, insurance, securities investment business, fintech and investment funds, and a good understanding of the global and onshore regulatory landscape.

The firm has long-standing and professional relationships with industry regulators in its various offices around the globe, coupled with a wealth of experience assisting some of the world's largest financial services businesses in implementing change to meet the requirements of new laws and regulations. The firm has helped to shape much of the law and regulations that impact its clients, be it through active participation in various industry bodies and regulatory committees, through consultation on new laws or direct dialogue with the regulatory body in each of its jurisdictions. Its regulatory experts have a deep understanding of the particular sector of the financial services industry in which they advise, be it banking, insurance, securities investment business, corporate administration or investment funds. In this way, it stands out from its competitors in that its regulatory lawyers are also specialists in the applicable sector, rather than regulatory generalists.

Winchester Search is a boutique independent search and selection firm serving the offshore, Asian, Australian and London markets. Simon Scott, head of our offshore practice, has specialised in recruiting lawyers for offshore law firms since 2009 including working in Grand Cayman for four and a half years during this period. He is a Cambridge University graduate who initially practised as an employment lawyer before switching to legal recruitment in 1996. With over a decade's experience of the offshore market behind him, he has forged strong relationships with managing partners, heads of department and senior HR personnel at all the major offshore firms. 

There are several compelling reasons why a significant number of lawyers from the world’s leading international law firms across the globe decide every year to make a combined career and lifestyle move to Cayman, BVI and Bermuda:


Due to the low tax rates, you can earn more than at Magic or Silver Circle firms in London, whilst working more predictable hours, still being able to undertake interesting, high-value work on behalf of major blue-chip clients, and having greater client contact and opportunity for travel and business development.

Quality of life

(a)  Superb climate (average daily high temperatures range from 29C - 33C in Grand Cayman; 28C – 31C in BVI; and 20C – 30C in Bermuda). 

(b)  Much shorter commute to work (whether on foot or by bike, scooter or car).

(c)  Being able to live in close proximity to the ocean. 

(d)  Far more relaxed nature of island life. 

(e)  Extremely picturesque surroundings where there is virtually zero air pollution.

(f)  The climate lends itself to participation in sport and outdoor activities, whether water sports and activities (swimming, snorkelling, paddle-boarding, kitesurfing, scuba diving, fishing, sailing, jet-skiing, canoeing), team sports (there are leagues for football, cricket, rugby, hockey etc) or individual sports and activities (cycling, jogging, crossfit, outdoor yoga, golf, tennis).   

Ease of transition

All the islands have English as their main language and have a very friendly, lively and cosmopolitan expat community (circa 50% of the population in Bermuda, BVI and Cayman are expats drawn from every corner of the globe), which makes settling into island life much easier. In addition, no exams are necessary to get admitted and practise in Cayman, BVI or Bermuda.

Please note that we are only able to respond to applicants who satisfy the criteria set out in the job spec above and whom we believe will be of interest to our clients.

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