Dylan was born and raised in the Cayman Islands and brings a local’s insight with a global perspective. After attending university in the United States, he returned home and proudly represented the Cayman Islands as a member of the National Rugby Team.
Dylan currently supports operations and client services at Navigate, where he plays a key role in ensuring a seamless experience for our clients. Prior to this, he held a managerial position at Strategic Wealth Preservation, where he specialized in assisting high-net-worth individuals with offshore precious metals investments.
His blend of local knowledge, international experience, and a client-first mindset makes him a valuable part of the team.
Email: Dylan@navigate.ky
With over 22 years of living and working in the Cayman Islands, Tarah Lawson offers a deep understanding of the island’s culture, lifestyle, and logistics. Her background in real estate has provided her with a strong foundation in navigating local systems, neighbourhood insights, and curating housing options. This paired with her strong community interest makes her an invaluable guide for individuals, families, and companies making the move to Cayman.
Tarah is passionate about making relocation feel less like a process and more like an exciting new chapter. She brings clarity and confidence to every step; whether helping you understand how to open utility accounts, explaining the ins and outs of work permits, or introducing you to trusted local service providers. Her strength lies in her ability to tailor every move to the person behind it.
When she’s not helping others settle into life in Cayman, Tarah enjoys quality time with her husband, son, and two spirited dogs. A creative at heart, she’s a published children’s book illustrator with a passion for painting and interior design. Her keen eye for detail and love of turning houses into homes naturally extends to helping newcomers feel comfortable and inspired in their new space.
Email: Tarah@navigate.ky
Conroy has lived in the Cayman Islands for over 10 years. He started his career in Jamaican Law Enforcement rising to the department level of Special Intelligence. His role included liaising with the FBI, US Embassy and Jamaica Constabulary Force’s National Intelligence Bureau. His background includes management roles in industrial security, risk mitigation and specialized escort and concierge services.
Conroy is certified in Criminal Intelligence Analysis, Safe Crisis Management, Terrorism Financing, Financial Investigations, and other Managerial disciplines. He is an excellent Operations Manager who can handle just about anything, on time, with confidence, and a unique sensitivity to all situations.
Email: Conroy@navigate.ky
Roberta moved to the Cayman Islands from the UK over 30 years ago. She has extensive knowledge regarding the culture of the Cayman Islands having held positions such as Director of Marketing & Public Relations for the Cayman National Cultural Foundation and Executive Director of Special Projects & Events for the Cayman Islands Government. She also served as Communications Director for the Chamber of Commerce and has written for several local publications. Roberta has both created and organised many large events including Film Festivals, Conferences, and National Celebrations. She has raised two children on Grand Cayman and has a wealth of advice on schooling options, health and wellness, real estate, and grass roots living.
Email: Roberta@navigate.ky
Stuart was born and raised in the Cayman Islands starting his career with the Royal Cayman Islands Police Service. Moving into the private sector in 2001, he successfully took a private security company to $20m in annual sales with large public and private contracts throughout the Caribbean. Stuart has an eye for identifying new business trends that has resulted in many successful personal business ventures, including one of the top offshore precious metals storage facilities in the world. He is a keen advocate for inward investment into the Cayman Islands and has been proud to contribute his time to serve with both government appointed boards and community service clubs. Stuart has extensive international business experience in both the Caribbean and the US.
Email: Stuart@navigate.ky
