Associate - Insurance - Cayman Islands
Date: 26 Jun 2026
Location: Grand Cayman, KY, KY1-9001
Company: Walkers Global

We are a leading international law and professional services firm providing legal, corporate and fiduciary services to global corporations, financial institutions, capital market participants and investment fund managers. With a global presence spanning the Americas, Europe, the Middle East and Asia, we advise on the laws of Bermuda, the British Virgin Islands, the Cayman Islands, Guernsey, Ireland and Jersey.
We treat everyone as the intelligent professional they are. Our approach is to trust and empower our people to deliver consistently, and enable them to succeed. Diversity is our secret weapon – it’s the sheer breadth of Walkers people that makes us who we are – gathered from across the globe and fluent in languages, jurisdictions and cultures that help us to mirror our clients and keep our own thinking in tune with the world in which we operate.
Overview of role
We seek suitably qualified Associates, preferably Caymanians or Residents with Employment Rights holders, who are talented and highly motivated to join our dynamic Insurance team, in the Cayman Islands. This is an exceptional opportunity to work on cutting-edge legal matters for high-profile clients and be involved in a wide range of complex and rewarding legal work.
Duties, Responsibilities & Person Specification
Associates (5-10 PQE)
Insurance, Cayman Islands
Multiple Vacancies
Salary Band US$180,000 - US$280,000
- To work with colleagues and client across multiple jurisdictions, to undertake insurance cross-jurisdictional analysis and provide a holistic solution, an essential skill where we have multi-national clients that are facing similar regulations in different jurisdictions.
- Must be willing and able to work outside standard business hours to support multiple time zones and offer advice and support on as needed basis to the wider business — allowing the practice to undertake cross-jurisdictional analysis as above.
- Provide high-quality, commercially focused advice on the full range of Cayman insurance matters, including governance, capital requirements, portfolio transfers, M&A, restructurings, reinsurance, SPC and PIC structuring, insurance-linked securities transactions, and corporate transactions.
- Draft and negotiate complex documents, including transactional documents, policyholder materials, board/resolution packages, governance frameworks, reinsurance agreements and due diligence reports.
- Act as a day-to-day client contact, managing expectations, clarifying instructions, and ensuring smooth matter progression.
- Support partners on business development initiatives, contributing to pitches, proposals, client alerts, market updates and industry presentations.
- Must have a deep understanding of the Cayman Islands financial services regulatory landscape, including insurance and reinsurance (across all licence classes), insurance management, banking, securities, investment funds, and fintech, with a good understanding of the global and onshore insurance landscape.
- Providing technically sound advice and highly responsive service to clients.
- Developing and expanding client relationships important to the Firm’s success at the same time becoming a valued resource to clients.
- Supporting colleagues, senior counsel and partners on matters using the global network to build the Firm resources.
- Maintaining a sustained record of revenue generation and profitability.
- Adhering to Firm’s values, professional ethics, and procedures.
- Participating in the development of the practice’s know-how, share knowledge, and occasionally participate in conferences, seminars and internal training
Education, Skills & Experience
- Qualified in the Cayman Islands or in another Commonwealth jurisdiction with a minimum of 5 years of post-qualification experience.
- Minimum of an Upper Second-Class (2.1) Honours law degree from a Tier 1 University is preferred.
- Experience working in a top-tier international or leading offshore law firm with responsibility to build and improve drafting skills on client matters and anticipating all issues that could arise when addressing a client's circumstance.
- Demonstrated ability to manage personal financial performance against pre-agreed targets and to contribute to team billing objectives.
- Must have a proven track record in managing and supporting partners on complex legal transactions and the ability to research new trends and keep up-to-date with existing legislative updates or themes.
- Demonstrated ability to perform above and beyond expectations in a fast-paced and high-performance culture while delivering an accurate and timely work product.
- Highly skilled and proficient in written and verbal communication.
- Experience working with legal precedents and law firm management tools including timekeeping and billing systems.
- Relevant business development and marketing experience to support efforts to attract new clients and develop new initiatives, within a top tier international or leading offshore law firm.
- Commercial awareness of the international reinsurance market, including emerging trends in insurance-asset management convergence and insurance-linked investment structures.
- Ability to work in a collaborative environment, a team player, willing to support others regardless of personal role or task and to help others in identifying development needs and subsequent training e.g. assist with training new joiners in the team.
- Actively participate in learning and development opportunities, as well as mentoring junior lawyers or article clerks in the team.
Walkers offers a dynamic working environment with opportunities for career progression and an excellent remuneration package, including a discretionary performance-based bonus, pension and fully covered health insurance for employees and 5 weeks' vacation. Remuneration will commensurate with qualifications and experience.
#LI-MC1
Walkers global is an equal opportunity employer. Equality and diversity are key to our global identity and an integral part of our goal to continue being an employer of choice. We are committed to a work environment that supports all individuals irrespective of gender, ethnicity, nationality, race, religion, marital status, age, disability, pregnancy, sexual orientation, gender identity or any other applicable legally protected characteristics. We make every effort to ensure that employment opportunities are open and accessible to all purely on the basis of personal ability.
