Leadership at Maplewood Senior Living

Maplewood Senior Living Leadership

Gregory D. Smith
President & CEO

Mr. Smith founded Maplewood Senior Living and has become known as a leading innovator in the senior housing industry. Prior to entering senior housing, Mr. Smith was a successful real estate investor in the hospitality, residential, and office sectors. His career spans over 25 years. As President and CEO, he oversees all aspects of the Company and is actively involved in operations, development and growth.

As an active member in the community, Mr. Smith serves as Chairman of the Board of Directors for Ability Beyond, a non-profit organization currently employing over 900 associates and engaging over 500 volunteers. Mr. Smith is also a member on the board of directors of the Alzheimer’s Association New York City Chapter and Western Connecticut Health Network Development Fund, Inc., and a member of the Network's Foundation and Strategic Planning Committee, which is tasked with planning for Danbury Hospital, Norwalk Hospital, and New Milford Hospital.

A native of Massachusetts, Smith currently resides with his family in Fairfield County, Connecticut, where he remains active with civic and community-based organizations.

Thomas Y. Gaston
Chief Investment Officer

Mr. Gaston has worked for nearly 30 years in real estate development, including 16 years dedicated to the luxury senior housing sector. Gaston began his career with Leggat McCall Properties and Amicus Healthcare. The breadth of his experience involves managing the development of more than 2,000 senior living units over his career. Gaston’s experience also includes executive leadership roles at other well-regarded regional senior living organizations, where he oversaw Development and Acquisitions. Additionally, Mr. Gaston co-founded Northbridge Senior Living in Burlington, Massachusetts.

Shane Herlet
Chief Operating Officer

Mr. Herlet oversees all daily operations for Maplewood Senior Living. With a master’s degree in Gerontology from Miami University of Ohio, his career spans over 25 years in luxury senior housing industry. Mr. Herlet's experience includes executive leadership roles at numerous national senior living organizations. He has managed over 3,000 units of senior housing throughout his career. Mr. Herlet is known as a catalyst for operational excellence in the senior housing industry, including specialties in growth, leadership, resident satisfaction, and care, as well as stabilization. In addition, Mr. Herlet serves as the President of Maplewood Senior Living HEART Foundation, Inc., a 501 (c)(3) non-profit organization established to provide financial support to associates experiencing unexpected life circumstances.

Maplewood Senior Living


1 Gorham Island Westport, CT 06880


  • Arthur E. Miller, Esq, General Counsel
  • David Cahill, Associate General Counsel


  • Brian Geyser, APRN-BC, MSN, Vice President of Clinical Innovation and Population Health
  • Amy Silva-Magalhaes, Senior Vice President of Community Operations  
  • Heather Freemont, Vice President of Marketing 


  • Jacques Preval, Vice President of Community Accounting
  • Victoria Rickert, Corporate Controller​