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Jay Webster



"Jay Webster - Jay is responsive, attentive and a great listener. He approaches every matter thoughtfully and with a clear head. He strikes the balance between providing enough information for us to take an informed decision but not too much information, leaving you feeling overwhelmed or unclear. He reads situations (and people) well and has excellent judgment."

Legal 500 Caribbean

"Jay is responsive, pragmatic, extremely knowledgeable and resourceful."

Chambers and Partners

"Jay is responsive, knowledgeable and provides sound advice."

Chambers and Partners



Jay Webster is a partner in the dispute resolution team at Carey Olsen Bermuda specialising in employment and immigration law matters. Jay has more than 15 years’ experience advising multinational companies, partnerships, LLPs and senior executives on all aspects of employment and immigration law.  Jay's practice is diverse and his clients include both local and exempt companies involved in a wide variety of sectors including telecoms, insurance and reinsurance, digital assets, financial and professional services.  

Jay regularly provides clients with strategic advice on commercially sensitive employment matters often with significant reputational implications including complex workplace and regulatory investigations, high value discrimination and bonus claims, and crisis management scenarios.  Jay prides himself on taking a pragmatic, commercial and business focused approach to all his work.

In particular, Jay enjoys resolving high value disputes, and has significant experience advising clients on: senior executive dismissals; multi-jurisdictional workplace restructures; trade union disputes; business protection issues (enforcement of restrictive covenants, team moves and breaches of confidentiality); privacy law and data protection issues and sensitive grievance and disciplinary investigations. 

Jay is a member of Carey Olsen Bermuda's Regulatory Team and acts as a Panel Chair in the Bermuda Human Rights Tribunal. Whilst practicing in the UK, Jay was named as a recommended employment law practitioner in the UK Legal 500 (London Human Resources: Employer and Senior Executives).


Jay joined Carey Olsen as a senior associate in January 2019 and was made partner in June 2022. Prior to joining Carey Olsen, Jay was a senior associate at the London office of a large US law firm.

Jay qualified as a solicitor in England and Wales in September 2008. He graduated from Leeds University with degree in History (2003) and subsequently obtained a Post Graduate Diploma in Law (2004) from BPP Law School London and completed his Legal Practice Certificate (2005) at BPP Law School Leeds.

Jay also regularly presents seminars to HR professionals, executive management teams and Company Boards on the latest employment and immigration issues and provides bespoke in-house training sessions for employers. In addition, Jay has written extensively on employment law for both internal and external publications.


Carey Olsen Bermuda Limited is a company limited by shares incorporated in Bermuda and approved and recognised under the Bermuda Bar (Professional Companies) Rules 2009. The use of the title “Partner” is merely to denote seniority. Services are provided on the basis of our current terms of business, which can be viewed at:


Awards and accolades


Jay is ranked in Chambers Global 2024 for 'Up and Coming: Dispute Resolution'.

Jay Webster Chambers Global 2024