About Sandals® Resorts: The History, Brands & People

Winston Anderson

Managing Director, Eastern Caribbean

As a hospitality professional with nearly 40 years of experience in Food and Beverage, Accounting, Rooms Division, Sales and Marketing, and Project Management, Winston’s journey with Sandals Resorts is well-known. Winston began working with the Sandals Resorts team in 1991 as a Food & Beverage Manager at Sandals Ochi and later advanced to hold successively progressive roles including Hotel Manager and then General Manager across the group. His most recent promotion in 2017 saw him being appointed Managing Director, Sandals Grande St. Lucian with oversight for all three Saint Lucian resorts. As of 2021, Winston’s role has expanded to include overseeing the islands of Grenada and St. Vincent and the Grenadines, in addition to his duties as Managing Director for all Saint Lucian resorts.

Karen C. Barnaby-Swaby

Financial Controller, Technical Services Division

Having in excess of 20 years’ experience in the hospitality industry, Karen currently supports the dynamic Technical Services Division which has responsibility for new construction, acquisition, renovation and branding of the resorts under the Sandals Resorts and Beaches Resorts brands. Prior to her appointment as Financial Controller of the Technical Services Division, Karen served as Financial Controller for Sandals Grande Antigua and Sandals Royal Plantation, having been promoted from Assistant Financial Controller at Beaches Negril and serving as Management Accountant at the SRI Corporate Office. During her tenure, she has undertaken the training and development of several finance teams across the Group and has been the recipient of awards including Financial Controller of the Year 2007 for the Group Finance Team and MVP of the Year 2017 for Sandals Resorts International. Karen is a Fellow of the Institute of Chartered Accountants of Jamaica, a member of the American Institute of Certified Public Accountants and a Chartered Global Management Accountant. She studied at the University of Technology, Jamaica, and holds degrees in Business and Accounting. She also earned her MBA in Business Administration and Management at the Nova Southeastern University, Florida.

Joanne Pearson

Director, Corporate Reporting

As a skilled financial expert with over 30 years of robust corporate finance experience, Joanne has demonstrated a history of excellence in the hospitality industry. Over the years, she has honed and developed competencies in hospitality analytics, creating and managing budgets and cash flow, business planning and external audit. As Director of Corporate Reporting, Joanne has direct responsibility for the Business Intelligence System that tracks the daily, weekly and monthly KPIs for the Sandals Resorts Group. She also meticulously provides and prepares budget guidelines, consolidates and analyzes budget files and facilitates budget reviews on behalf of the group. With her vast knowledge and wealth of experience, Joanne has contributed significantly to the financial health and stability of the Sandals Group. In addition to being a chartered accountant through the Institute of Chartered Accountants in England and Wales and a graduate of the University of the West Indies, Joanne is also a member of the Audit and Payables Committees for Sandals Resorts International.

Jessica Shannon

Chief Experience Officer

Serving as a global industry leader with extensive consulting experience in market development, market positioning and customer experience, change management, organizational transformation and more, Jessica Shannon joined Sandals Resorts International’s team as Chief Experience Officer.

Jessica is responsible for enhancing the company’s award-winning approach to delivering best-in-class, experiences across the entire guest journey, from booking through to returning home. She also leads the global strategy for new and innovative experiences based on evolving traveler demand and shifting world scenarios. Additionally, Jessica utilizes her recognized expertise to ensure that team members enjoy a workplace centered on human-design, fostering an inspiring, transparent and sustainable culture that allows team members to do their best work together.

Jessica holds an MBA from Harvard Business School and a Bachelor of Science in Finance and International Business.

Heidi Clarke

Executive Director

Born and raised in Jamaica, Heidi has extensive experience in the education, social services and business management fields. As the Executive Director of the Sandals Foundation – the philanthropic arm of Sandals Resorts International which focuses on developing the Caribbean and improving the lives of its people through the areas of education, environment and community – Heidi manages development projects across nine Caribbean islands.

By harnessing the power of volunteerism and activism led by team members, guests, travel agents, local, regional, international, nonprofit organizations, and corporate partners, Heidi and her team execute life-changing programs that go beyond the doors of Sandals and Beaches Resorts.

Heidi sits on the board of the Caribbean Hotel and Tourism Association Education Foundation and is a Director on the board of Nudge Caribbean. In Jamaica, she is a certified Game Warden with the National Environment and Planning Agency and a member on the boards of the Fish Sanctuary Network, the North East Regional Health Authority Fundraising Committee, Culloden Early Childhood Institute, and the Freedom Skatepark Committee.

Heidi graduated from the University of Miami, where she studied child psychology and education while working with children and underprivileged schools in the South Florida community.

Shawn DaCosta

Chief Strategy Officer

With an impressive background working at and leading at several resorts in Jamaica and the Turks and Caicos Islands, complemented by international experience at luxury resorts in Italy and London, Shawn DaCosta in his current capacity as Chief Strategy Officer at Sandals Resorts International, works closely with the chain’s Chief Executive Officer and Executive Chairman, managing the day to day operations of all 19 resorts in the region and leading a dynamic team to maintain the highest standards across the group. Since joining the company in 1991 as a management trainee, Shawn has distinguished himself to become an integral member of the Sandals Resorts Executive team – holding various roles over his tenure including Food and Beverage Manager at Sandals Montego Bay and Sandals Dunn’s River, and Director of Operations at Beaches Turks & Caicos. After an impressive display in Turks and Caicos, he was asked to join the team at Sandals Resorts International as Director of Operations in 2006, and was responsible for all resort operations within the company’s portfolio, with direct reporting from all General Managers and responsibility for all partnership relations.

Spearheading numerous successful resort openings, Shawn has consistently demonstrated impressive management skills and operational know-how, generating new initiatives and ideas to efficiently grow the company’s operations, becoming the Chief Operations Officer in 2016. He created and implemented the chain’s first Standard Operating Procedures document for all departments, played a fundamental role in establishing the corporate procurement division and led the development of the company’s award-winning COVID-19 response, the Sandals Platinum Protocols of Cleanliness.

Shawn was educated in The Netherlands at Stenden University where he was named valedictorian; in The United States and Jamaica and has spent his entire career in the hospitality industry.

Winston Anderson

Managing Director, Eastern Caribbean

As a hospitality professional with nearly 40 years of experience in Food and Beverage, Accounting, Rooms Division, Sales and Marketing, and Project Management, Winston’s journey with Sandals Resorts is well-known. Winston began working with the Sandals Resorts team in 1991 as a Food & Beverage Manager at Sandals Ochi and later advanced to hold successively progressive roles including Hotel Manager and then General Manager across the group. His most recent promotion in 2017 saw him being appointed Managing Director, Sandals Grande St. Lucian with oversight for all three Saint Lucian resorts. As of 2021, Winston’s role has expanded to include overseeing the islands of Grenada and St. Vincent and the Grenadines, in addition to his duties as Managing Director for all Saint Lucian resorts.

Karen C. Barnaby-Swaby

Financial Controller, Technical Services Division

Having in excess of 20 years’ experience in the hospitality industry, Karen currently supports the dynamic Technical Services Division which has responsibility for new construction, acquisition, renovation and branding of the resorts under the Sandals Resorts and Beaches Resorts brands. Prior to her appointment as Financial Controller of the Technical Services Division, Karen served as Financial Controller for Sandals Grande Antigua and Sandals Royal Plantation, having been promoted from Assistant Financial Controller at Beaches Negril and serving as Management Accountant at the SRI Corporate Office. During her tenure, she has undertaken the training and development of several finance teams across the Group and has been the recipient of awards including Financial Controller of the Year 2007 for the Group Finance Team and MVP of the Year 2017 for Sandals Resorts International. Karen is a Fellow of the Institute of Chartered Accountants of Jamaica, a member of the American Institute of Certified Public Accountants and a Chartered Global Management Accountant. She studied at the University of Technology, Jamaica, and holds degrees in Business and Accounting. She also earned her MBA in Business Administration and Management at the Nova Southeastern University, Florida.

Joanne Pearson

Director, Corporate Reporting

As a skilled financial expert with over 30 years of robust corporate finance experience, Joanne has demonstrated a history of excellence in the hospitality industry. Over the years, she has honed and developed competencies in hospitality analytics, creating and managing budgets and cash flow, business planning and external audit. As Director of Corporate Reporting, Joanne has direct responsibility for the Business Intelligence System that tracks the daily, weekly and monthly KPIs for the Sandals Resorts Group. She also meticulously provides and prepares budget guidelines, consolidates and analyzes budget files and facilitates budget reviews on behalf of the group. With her vast knowledge and wealth of experience, Joanne has contributed significantly to the financial health and stability of the Sandals Group. In addition to being a chartered accountant through the Institute of Chartered Accountants in England and Wales and a graduate of the University of the West Indies, Joanne is also a member of the Audit and Payables Committees for Sandals Resorts International.

Jessica Shannon

Chief Experience Officer

Serving as a global industry leader with extensive consulting experience in market development, market positioning and customer experience, change management, organizational transformation and more, Jessica Shannon joined Sandals Resorts International’s team as Chief Experience Officer.

Jessica is responsible for enhancing the company’s award-winning approach to delivering best-in-class, experiences across the entire guest journey, from booking through to returning home. She also leads the global strategy for new and innovative experiences based on evolving traveler demand and shifting world scenarios. Additionally, Jessica utilizes her recognized expertise to ensure that team members enjoy a workplace centered on human-design, fostering an inspiring, transparent and sustainable culture that allows team members to do their best work together.

Jessica holds an MBA from Harvard Business School and a Bachelor of Science in Finance and International Business.

Heidi Clarke

Executive Director

Born and raised in Jamaica, Heidi has extensive experience in the education, social services and business management fields. As the Executive Director of the Sandals Foundation – the philanthropic arm of Sandals Resorts International which focuses on developing the Caribbean and improving the lives of its people through the areas of education, environment and community – Heidi manages development projects across nine Caribbean islands.

By harnessing the power of volunteerism and activism led by team members, guests, travel agents, local, regional, international, nonprofit organizations, and corporate partners, Heidi and her team execute life-changing programs that go beyond the doors of Sandals and Beaches Resorts.

Heidi sits on the board of the Caribbean Hotel and Tourism Association Education Foundation and is a Director on the board of Nudge Caribbean. In Jamaica, she is a certified Game Warden with the National Environment and Planning Agency and a member on the boards of the Fish Sanctuary Network, the North East Regional Health Authority Fundraising Committee, Culloden Early Childhood Institute, and the Freedom Skatepark Committee.

Heidi graduated from the University of Miami, where she studied child psychology and education while working with children and underprivileged schools in the South Florida community.

Shawn DaCosta

Chief Strategy Officer

With an impressive background working at and leading at several resorts in Jamaica and the Turks and Caicos Islands, complemented by international experience at luxury resorts in Italy and London, Shawn DaCosta in his current capacity as Chief Strategy Officer at Sandals Resorts International, works closely with the chain’s Chief Executive Officer and Executive Chairman, managing the day to day operations of all 19 resorts in the region and leading a dynamic team to maintain the highest standards across the group. Since joining the company in 1991 as a management trainee, Shawn has distinguished himself to become an integral member of the Sandals Resorts Executive team – holding various roles over his tenure including Food and Beverage Manager at Sandals Montego Bay and Sandals Dunn’s River, and Director of Operations at Beaches Turks & Caicos. After an impressive display in Turks and Caicos, he was asked to join the team at Sandals Resorts International as Director of Operations in 2006, and was responsible for all resort operations within the company’s portfolio, with direct reporting from all General Managers and responsibility for all partnership relations.

Spearheading numerous successful resort openings, Shawn has consistently demonstrated impressive management skills and operational know-how, generating new initiatives and ideas to efficiently grow the company’s operations, becoming the Chief Operations Officer in 2016. He created and implemented the chain’s first Standard Operating Procedures document for all departments, played a fundamental role in establishing the corporate procurement division and led the development of the company’s award-winning COVID-19 response, the Sandals Platinum Protocols of Cleanliness.

Shawn was educated in The Netherlands at Stenden University where he was named valedictorian; in The United States and Jamaica and has spent his entire career in the hospitality industry.

Winston Anderson

Managing Director, Eastern Caribbean

As a hospitality professional with nearly 40 years of experience in Food and Beverage, Accounting, Rooms Division, Sales and Marketing, and Project Management, Winston’s journey with Sandals Resorts is well-known. Winston began working with the Sandals Resorts team in 1991 as a Food & Beverage Manager at Sandals Ochi and later advanced to hold successively progressive roles including Hotel Manager and then General Manager across the group. His most recent promotion in 2017 saw him being appointed Managing Director, Sandals Grande St. Lucian with oversight for all three Saint Lucian resorts. As of 2021, Winston’s role has expanded to include overseeing the islands of Grenada and St. Vincent and the Grenadines, in addition to his duties as Managing Director for all Saint Lucian resorts.