EXPERIENCE

Nick Joseph

Founder

After more than 25 years as a Cayman Island’s lawyer specialising in regulatory matters, including the provision of advice in respect of immigration and employment matters, and an emphasis on relocation, Nick is the Founder of Reside. Nick’s career as an Attorney-at-Law spanned two law firms.  In each case he formed and led the Cayman Business Teams specialising in assisting individuals already settled in these Islands, as well as those who choose to make the Cayman Islands the place to live and raise their families, and in which, and from which, to conduct business. He is well known and respected for his extensive knowledge of the workings of Cayman’s Immigration rules and regulations. A lifelong resident of the Cayman Islands and admitted Attorney-at-Law since 1997, Nick was educated in the Cayman Islands, United Kingdom, United States, and France.   He is passionate about Cayman, its culture and its people and is enthused by many of the remarkable people who choose to settle and to make the Islands their home for the benefit of themselves and those already here. Although Nick continues to be a lawyer, that role is separate and aside from his position with Reside. Nick is an Accredited Mediator and Notary Public.  He has served on a range of Government committees which include the Adoption Board, the Investors in People Committee, The Local Companies (Control) Law Review Committee and the Financial Services Subcommittee on Immigration. He has also sat as Technical Advisor to the Immigration Review Team, and as the Deputy Chairman of the Minimum Wage Advisory Committee in 2014 when the minimum wage was first introduced to the Cayman Islands. Nick has also served as a Member of Council of the Caymanian Bar Association, as well as Treasurer and Secretary of that organisation for multiple terms. Nick was a guest lecturer at the Truman Bodden Law School assisting with the education and qualification of law school graduates seeking to pass the Professional Practice Course toward qualification as a Cayman Islands Attorney-at-Law. He frequently leads seminars for the Cayman Islands Chamber of Commerce and The Cayman Islands Society of Human Resource Professionals helping to equip business persons and HR professionals with the knowledge and understanding necessary to navigate aspects of Cayman’s nuanced regulatory regime.

Diana Joseph

Chief Operating Officer

Diana holds the role of Chief Operating Officer for Reside and has been instrumental in the design of its systems. She has a background in logistics and operations and has worked in both the legal and financial service sectors before establishing her own business. Originally from the UK, Diana worked in asset and property management in the City of London. After spending some time in Los Angeles, Diana moved to the Cayman Islands in 1996 and spent several years as Clerk to the late Pierre LaMontagne, QC. Following his passing, Diana assumed a role with a leading global accountancy firm where amongst other projects she worked with an international team coordinating multi-jurisdictional litigation and related discovery. For more than 15 years Diana has traded as Prism, providing business administration, project and property management services for a small and discrete number of both local and international clients, drawing on her many years of experience working on the periphery of the property and development industries. Since 2012, she has served on the Board of Directors of Jasmine, (a leading local charity providing palliative and hospice care) and is a current Vice Chair. She has served in other capacities since moving to the Islands and her roles have included several years sitting as a member of the Planning Appeals Tribunal.

Nicole D'Heer Watson

Senior Manager

Nicole is a Senior Manager with Reside and brings over two decades of leadership experience across People and Culture, Marketing, Operations, and Finance. Known for her strategic vision and ability to build high-performing, purpose-driven teams, she has guided organizations through growth and transformation across multiple jurisdictions. Before joining Reside, Nicole held a C-Suite role at a leading offshore law firm, where she spearheaded initiatives in HR, marketing, and business development. At Reside, she leverages her expertise to enhance operational excellence and client experience, ensuring every interaction reflects the company’s commitment to quality and integrity.

Kendra Okonski

Assistant Manager

Kendra Okonski is the Assistant Manager at Reside Cayman, a role that entails recruitment, training and supervision of staff, alongside bespoke design and development of technical systems suited to Reside’s services. Kendra is an experienced communications professional, specialising in economics and public policy. Her career has spanned more than two decades working collaboratively with public policy experts and think tanks, as well as with the global news media and opinion formers. Prior to joining Reside, she worked as a Senior Policy Advisor for the Cayman Islands Government’s Ministry of Investment, Innovation and Social Development. Leaning on an array of diverse technical skills, she founded the 345Robotics Foundation and actively works as a volunteer STEM/robotics educator for young people. She currently is completing a Master’s Degree in Blockchain and Digital Currency, and is the author/editor of numerous scholarly articles and books.

Cindy Downing

Client Liaison

Cindy Downing brings more than 20 years of senior-level human resources experience across some of the Cayman Islands’ largest and most dynamic organisations. Known for her calm, solutions‑driven approach, Cindy has built a career as a trusted advisor to leadership teams, guiding them through complex people, compliance, and organisational challenges. Her extensive background in HR operations, including immigration management, policy development, talent acquisition, performance management, and change leadership, equips her with a deep understanding of client needs and the intricacies of Cayman’s immigration landscape. Cindy excels at simplifying complex processes, building strong relationships, and supporting clients with clarity and care. A natural collaborator, Cindy is passionate about service excellence and helping individuals and businesses navigate their immigration journey with confidence.

Anton Nelson

Client Liaison

Anton Nelson is a Client Liaison with Reside and his experience across both private-sector consulting and financial services enables him to anticipate client needs, strengthen relationships, and contribute to the continued enhancement of Reside’s service standards. He excels at supporting clients through complex processes while fostering clarity, trust, and seamless communication. Before joining Reside, Anton held key roles in business advisory and business banking, where he supported organizational decision-making and guided clients through strategic and operational challenges. He also founded Athletes Ahead, an agency specialising in providing Caymanian student-athletes with international academic and athletic opportunities. At Reside, he leverages his background in governance, due diligence, and relationship stewardship to ensure each client receives an informed, responsive, and values-driven experience aligned with the company’s commitment to excellence. Anton holds both a Bachelor of Science and a Master of Science in Business Management, as well as a specialist certification in anti-money-laundering practices. In addition to his professional accomplishments, he represents the Cayman Islands as a national team player, bringing dedication, discipline, and a team-oriented approach to every aspect of his work.

Grace Edgington

Client Liaison

Grace brings a strong academic foundation and diverse experience across legal, healthcare, and professional services to her role as Client Liaison at Reside Cayman. Holding a Postgraduate Diploma in Law (PGL), her unique blend of legal insight and client-focused expertise makes her an invaluable addition to the Reside team. Her career has been defined by a commitment to guiding individuals through complex and sensitive processes with clarity, empathy, and professionalism. Grace has served as the first point of contact for clients in high-pressure environments, building trust and delivering results through meticulous case management and compliance oversight. From supporting vulnerable individuals in London’s legal sector to advocating for wellness needs in Cayman’s healthcare community, Grace has consistently demonstrated discretion, accuracy, and a passion for client care. Her ability to navigate documentation, regulatory requirements, and cultural nuances makes her exceptionally well-placed to assist clients with immigration matters.

Lillian Coleman

Client Liaison

As Client Liaison at Reside, Lillian works closely with founder Nick Joseph, primarily supporting Permanent Residency applications. With over nine years of experience in immigration law and administrative support, she is dedicated to ensuring compliance and delivering a seamless client experience. Lillian’s background includes formal legal training and hands-on experience in Cayman immigration and legal support at a respected local law firm. She is highly skilled in research, information gathering, drafting, and legislative monitoring, as well as managing confidential data and navigating high-pressure situations with precision. Her approach is thorough, adaptable, and solution-focused, consistently driving efficiency and positive outcomes for clients and the team. 

Michael Matthews

Client Liaison

Michael serves as a key point of contact for Reside clients, guiding them through Cayman’s immigration processes with clarity and care. He specialises in residency applications, and related compliance matters, ensuring a smooth and efficient experience for every client. Before joining Reside, Michael managed daily operations for a proprietary trading firm in Grand Cayman, where he oversaw office administration, onboarding, and work permit processes. His career also includes roles in recruitment, finance assistance, and property administration, giving him a well-rounded perspective on client service and operational excellence. Michael holds a BA (Hons) in International Relations from the University of Exeter and is passionate about helping clients navigate complex immigration requirements while delivering exceptional service.

Sidehan Vallecillo

Administrative Assistant

Sidehan Vallecillo is our Administrative Assistant and is an integral part of the Reside team. Sidehan works collaboratively with other members of our organisation to support clients, manage the office and liaise with external agencies, including, in particular, the Office of the Deputy Governor and the Department of WORC. Sidehan facilitates all manner of administrative functions and assists in the preparation and submission of a wide range of applications. Sidehan previously worked in both the Financial Services sector and in the Development industry and brings her experience in HR and Customer Service to us. She has an Associate’s Degree in Business Administration.