Cayman Islands (KY)
04 Feb 2021
04 Mar 2021
Full Time
Practice Areas
Banking/Finance, Corporate, Funds
7+ Years
Experience Level
Senior Level

This is a rare opportunity for a senior PSL lawyer at a leading global offshore law firm. You will need to have gained your experience at either a major international City firm or major offshore firm, and be admitted in either the UK, Australia, New Zealand or Canada. The successful candidate will have relevant work experience in either corporate, finance, or investment funds law and is expected to be able to communicate clearly, have an aptitude for project management, a proven track record of drafting legal documentation and a desire to promote excellence. This will be a highly visible role involving a high level of responsibility supporting lawyers and professionals across the firm. The PSL will offer support to offices in other jurisdictions and be involved in firm-wide projects. role principally involves:

  • reviewing, drafting and maintaining precedents;
  • monitoring and summarising legislative developments (for both internal and external updates);
  • preparing legal guides and practice notes; and
  • developing and maintaining the firm's precedent systems (current experience of knowledge management technology and document automation systems would be an advantage for the successful candidate).
  • The PSL will work alongside the firm's existing PSL team to ensure that a consistent level of quality support is offered. 

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, is a Cambridge University law graduate and former employment lawyer who has worked in legal recruitment since 1996 and specialised exclusively in the offshore market since 2009, including living and working as a legal recruiter in Grand Cayman for almost five years. 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 as much as working for some of the highest-paying US firms in London and significantly more than working for Magic or Silver Circle firms in London, whilst -

(a)  working ​shorter and ​more predictable hours;
(b)  still being able to undertake interesting, high-value work on behalf of major blue-chip clients;
(c)  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 (a) have English as their main language and (b) 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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