Our Leadership Team

Jake Kilkeary

Jake Kilkeary

Corporate Director of Real Estate/Development

Jake is the Corporate Director of Real Estate/Development at Prospera Hospitality, and he is the President of Westmoreland Payment Services (WPS). While working in the hotel and restaurant worlds since 2003, he has overseen the setup processes for PMS, POS, processors and gateways. He handles setting up cyber policies to make sure customers are protected from any out-of-pocket expenses due to hacking emergencies.

After working as a restaurant manager at Bigelow Grille and general manager at Damon’s Restaurant, he worked as the VP of Development for Prospera for 14 years. He owns a real estate investment company and has been the owner of WPS since 2012.

Jake is a graduate of Florida State University and is a single digit golfer. He also donates his time at St. Anthony’s special needs program for children, Shadyside school for the blind, and the mission for Franciscan University.

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