2025 has been a year or continued elevation for the employees at Four Seasons Resort and Residences! We have seen the promotion and transition of several employees and most recently we have been the proud recipient of two acclaimed awards at the Anguilla Hotel and Tourism Gala Awards ceremony, namely, Conlloyd Gumbs as Supervisor of the Year and General Manager, Diego Stembert as Hotelier of the Year 2025!
Recognition as Hotelier of the year reflects Diego’s outstanding leadership, his commitment to our people, and his contribution to Anguilla’s tourism industry. Diego is a 30-year hospitality veteran whose worldwide experience has led him to his current role as General Manager of Four Seasons Resort and Residences Anguilla.
He joined Four Seasons in 2010 at Four Seasons Resort Nevis as Director of Rooms and has since held senior leadership roles across the brand, including General Manager at Four Seasons Resort Bora Bora and Four Seasons Hotel Buenos Aires, as well as Hotel Manager at Four Seasons Hotel Mexico City. In Diego’s own words, “There is something particularly special about life on a tropical island; it is absolutely surreal to wake up to this paradise every day. We know that our guests choose to be here to celebrate some of their most momentous occasions, so it is our mission to ensure that their stay with us is perfection.”
Conlloyd Gumbs joined the team in 2024 as an Engineering Supervisor and no sooner than he joined had his presence been felt. Conlloyd quickly became a trusted leader within his department and throughout the Resort. His knowledge, skills and humility has earned [him] much respect at work and within the community. Conlloyd is passionate about helping youth develop their skills in mathematics and often encourages them to stay motivated to achieve their goals and dreams.
We are extremely proud of our Team and our many accomplishments throughout 2025. We look forward to greater achievements in 2026!
