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Michael Cuthbertson has a diverse work experience in the real estate and hospitality industry. Michael has held various roles in different companies throughout their career. Michael started their career in 1997 as a Beverage Manager at The Peaks Hotel & Golden Door Spa in Telluride, Colorado. Michael then worked as a Resort Manager and Assistant Director of Food & Beverage at Island Outpost: The Tides Hotel & The Marlin Hotel in South Beach Miami, Florida from 2000 to 2001.

From 2001 to 2003, Cuthbertson worked as a Sales Operations Manager at Playground Destination Properties, where they were responsible for managing sales operations and support teams for luxury resort real estate properties.

Cuthbertson then worked as a Real Estate Sales Manager at Hyatt Residence Club from 2004 to 2008, where they managed the sales and marketing team for a fractional ownership development in Aspen, Colorado.

Michael also owned and operated CI Solutions, a company that developed customer information tools and strategies for real estate sales and marketing professionals. Michael worked as the Owner of CI Solutions from 2003 to 2008.

Cuthbertson's work experience also includes roles at Timbers Resorts, including Managing Director of Development - Hawaiian Islands from 2014 to 2017, Director of Asset Management / Project Director - Transitions & Acquisitions from 2010 to 2014, and Real Estate Sales Manager from 2008 to 2009.

Additionally, they have worked at Destination by Hyatt as an Area Vice President from 2017 to 2023, at Destination Residences Hawaii as a Principal Broker Hawaii, Realtor from 2016 to the present, and at Confluence Realty as an Employing Broker Colorado, Realtor since 2015.

Cuthbertson's current role is Senior Vice President of Residential Resort Management at CoralTree Hospitality, which they started in 2023.

Michael Cuthbertson attended the University of Washington from 1992 to 1997, where they studied Environmental Policy & Economics. In 1995, they also obtained a Certification in Emergency Medical Technology/Technician (EMT Paramedic) from Everett Community College. Additionally, they have obtained several certifications, including EcoBroker from EcoBroker International in 2009, Colorado Real Estate Employing Broker from the Colorado Department of Real Estate in 2006, and Hawaii Real Estate Principal Broker in 2016.