Senior Immigration Specialist

The Senior Immigration Specialist will support both internal HR immigration and our clients’ immigration service needs. Success in this position requires deep familiarity with Cayman Islands immigration regulations and government systems, strong organizational discipline, and the ability to balance client-facing responsibilities with internal HR priorities. This role will collaborate closely with the Head of Client Immigration, Attorney, and the HR Manager to ensure timely, compliant, and client-cantered outcomes.

WHAT WILL YOU DO

Internal Immigration Support:-

• Prepare and submit work authorization applications and renewals in a timely manner, gathering all required documentation and fees. This includes drafting cover letters for applications and compiling supporting materials as required by Cayman Islands Immigration authorities
• Oversee the immigration and work authorization process for all new expatriate employees, including those relocating to the Cayman Islands, to ensure compliance with Cayman Islands regulations prior to commencing employment
• Proactively manage and coordinate work authorization renewals, ensuring all applications are prepared and submitted within prescribed timeframes to maintain uninterrupted legal authorization for employees to work. Maintain a tracking system of all staff work permits and immigration documents, including expiry dates and status updates
• Lead the administration and oversight of the Firm’s Business Staffing Plan, ensuring regulatory compliance and aligning staffing allocations with evolving business objectives, operational requirements, and workforce needs.
• Provide guidance and support to ensure impacted employees and their managers fully understand work permit restrictions and/or requirements (i.e. Regulation 6 Condition training requirements)
• Act as a liaison with Workforce Opportunities & Residency Cayman (WORC), fostering positive working relationships to facilitate the efficient processing of immigration applications and related matters, including attending WORC offices as required to submit applications, collect processed documents and address immigration-related matters on behalf of the Firm..Monitor progress of applications, follow up proactively on any delays or issues, and inform management and employees of their application status
• Assist with ad hoc projects as assigned.

Client Immigration Support:-

• Under the guidance and direction of the firm’s Head of Client Immigration, Attorney provide comprehensive administrative support for client immigration matters, ensuring alignment with Cayman Islands immigration regulations.
• Prepare, review, and submit immigration applications on behalf of external clients, including work permit applications for client companies, permanent residency and citizenship filings, and other relevant documentation under Cayman immigration law.
• Collect, organize, and verify client-provided information and supporting documents for completeness, accuracy, and compliance with legal requirements.
• Maintain strict confidentiality and deliver high-quality client service, ensuring timely and professional handling of all immigration-related inquiries and processes.

WHAT WILL YOU NEED

• Minimum of 5+ years of hands-on experience in a Cayman Islands immigration role, ideally within a law firm, immigration services firm, or other professional services environment
• Demonstrated ability to operate autonomously as a subject-matter expert, managing the full immigration function end-to-end with minimal supervision
• Comprehensive working knowledge of Cayman Islands Immigration Law and Regulations, including the various work permit categories, the nine-year term limit, permanent residency criteria, and post-PR pathways (Naturalization, BOTC, and Caymanian Status applications)
• Proven experience preparing and submitting complex immigration applications, including work permits, permanent residency, and post-PR filings
• Established working relationships with Workforce Opportunities & Residency Cayman (WORC) and a track record of navigating the regulator effectively
• Strong working knowledge of the JobsCayman portal and the online payment/submission systems for work permits
• Solid understanding of Cayman's Labour Act and employment practices, given this role straddles HR and immigration functions (e.g. statutory requirements for employee benefits and termination)
• Experience mentoring, supervising, or providing guidance to junior immigration staff
• Ability to act as a trusted advisor to internal stakeholders and external clients, confidently explaining complex immigration requirements and regulatory changes in plain language
• Awareness of upcoming regulatory developments (including the new immigration regulations effective 1 May 2026) and the ability to adapt processes accordingly
• Exceptional administrative and organizational skills with a keen attention to detail
• Ability to juggle multiple matters and competing deadlines, maintaining well-organized files (both electronic and paper) across a high volume of filings
• Excellent written and verbal communication skills, including drafting cover letters, affidavits, and client-facing correspondence
• Strong interpersonal skills with a client-service orientation, supporting both internal staff and external clients through the immigration process
• Proficiency with standard office software (MS Word, Excel, Outlook) and immigration/case management databases
• High level of integrity and discretion when handling sensitive personal information for employees and clients
• A collaborative team player with a positive attitude and ownership mentality