Our Leadership

The Maplewood Leadership Team is made up of professionals with diverse talents and experiences who share a common goal — to redefine senior living. Their shared passion and commitment have led Maplewood to become an industry leader, setting new standards in the industry and inspiring a renewed outlook on life for residents and families.

Gregory D. Smith – President and CEO

Gregory D. Smith is a leading innovator in the senior housing industry. As president and CEO, he oversees all aspects of the company and is actively involved in operations, development and growth.

Greg has deep experience managing businesses that seamlessly incorporate residential, hospitality and health care facets. In his many years in real estate, he has developed a wide range of property brands, ranging from office buildings to full-service hotels.

In 2004, he created Maplewood Senior Living, with residences in Connecticut, Massachusetts and Ohio. In 2012, Greg and his team saw a new need that wasn’t being met: a very specific demographic was seeking an even higher level of luxury senior living — this time in an urban environment. Compelled to create a solution to fulfill this need, Greg and his team envisioned Inspῑr, a sister brand to Maplewood Senior Living.

A native of Massachusetts, Greg studied marketing and finance at Bentley University. He is a member of the board of directors of the Alzheimer’s Association, New York City Chapter, and currently resides with his family in Fairfield County, Connecticut.

Thomas Y. Gaston – Chief Investment Officer

Thomas Gaston has spent the majority of his career in real estate development, including nearly two decades dedicated to the luxury senior housing sector. As chief investment officer, Tom is responsible for growing the company’s portfolio through the developments and acquisition of both suburban and urban properties. He 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.

Tom’s experience also includes executive leadership roles in the areas of operations and development and acquisitions at a number of other well-regarded regional senior living organizations. Additionally, Tom co-founded Northbridge Senior Living in Burlington, Massachusetts.

Shane Herlet – Chief Operating Officer

Shane Herlet has more than 25 years of experience in the luxury senior living industry and has managed more than 3,000 units of senior housing throughout his career. He has been recognized for operational excellence in the industry for delivering unmatched senior living experiences that seamlessly integrate luxury accommodations, exceptional hospitality, cutting-edge technology, innovative wellness programs and world-class care. 

In addition to his responsibilities as COO, Shane serves as the president of Maplewood’s HEART Foundation, Inc., a 501 (c)(3) nonprofit organization established to provide financial support to associates experiencing unexpected life circumstances. He is also actively involved in a number of Alzheimer’s and senior living associations, including ESAAL, OALA, Mass-ALA, and CALA. Shane has a master’s degree in Gerontological Studies from Miami University.

Amy Silva-Magalhaes, MHA – Senior Vice President Of Community Operations

Amy Silva-Magalhaes is a seasoned senior living leader with 15 years of experience working at renowned senior living brands. Prior to that, Amy spent five years in hospitality management at Hilton, Marriott and Starwood hotels. As the senior vice president of Community Operations, Amy serves as the main connection point between resident care and operations — responsible for enterprise-wide strategic planning, execution, business alignment, leadership development, human capital, communication and company culture.

She is passionate about developing effective and efficient resident care operations that promote optimal outcomes for residents and staff and ensuring regulatory compliance companywide.  Amy holds a bachelor’s degree in Business Administration from Southern Connecticut State University and a master’s degree in Healthcare Administration from Post University. Amy sits on the board of the Connecticut Assisted Living Association and the Massachusetts Assisted Living Association.

Brian Geyser, APRN-BC, MSN – VP Clinical Innovation & Population Health

Brian Geyser is an experienced health care leader and seasoned clinician with an unrelenting drive to transform how we care for older adults. He is a strategic and innovative thinker well versed in emerging care models and population health strategies. 

Brian formerly served as clinical director for Commonwealth Care Alliance (CCA) where he helped lead the implementation of organizational development, care model improvement and transformation initiatives to strengthen and expand CCA’s next-generation care delivery and care management model in Massachusetts.  

Brian directs the Maplewood Senior Living Center for Aging Innovation & Technology and serves as chapter ambassador for Aging2.0, a global network that accelerates innovation to improve the lives of older adults around the world.  

Brian holds a Bachelor of Arts in Psychology from Arizona State University and a Master of Science in Nursing from Yale University.

Heather Freemont – Vice President Of Marketing

As Vice President of Marketing, Heather Freemont is responsible for expressing how Maplewood meets the needs of our residents and their families. From developing marketing plans to interpreting market data, her work truly keeps Maplewood top of mind in the senior living world. With more than 20 years of experience in the senior care industry, Heather understands the people we serve like no one else. 

Heather’s extensive background in the industry includes roles as vice president of Sales and Marketing for Judson Senior Living and Heather Hill/UHHS, as well as executive director for the Eliza Jennings Senior Care Network. Heather attended Kent State University where she earned a Bachelor of Arts in Family & Consumer Studies, Gerontology and Long-Term Care Administration, and is an OALA board member. Her valuable skill set and dedication to the industry make her an invaluable asset to the Maplewood team.

Arthur Miller – General Counsel

Arthur (Art) joined Maplewood over nine years ago and works with our executive management team. He is our steadfast legal counsel for all our business transactions, acquisitions and negotiations and represents the company with third parties, including outside counsel.  

Art graduated from Duke University, A.B., magna cum laude; and Georgetown University Law Center, J.D. He is a member of the Connecticut Bar Association.

Stefanie Wilk – Chief Accounting Officer

Stefanie brings 20 years of accounting experience to Maplewood. Before joining our team, she was the managing director at CFGI – Consulting Services and also worked as a senior manager, SEC/Financing Reporting at General Electric, and as senior manager/Audit at Deloitte.

Stefanie graduated from the University of Delaware with a Bachelor of Science in Accounting. She is a CPA in the state of Connecticut.

Jacques Preval – VP Of Community Accounting

As vice president of Community Accounting, Jacques primarily acts as a liaison between the communities, the accounting team and upper management. However, he has been known to have chameleon-like adaptation skills, and can step into another role wherever needed to make sure the team is supported. As far as he is concerned, his role is to help people and keep things moving forward. Before Maplewood, Jacques spent many years working in senior living communities in roles that included operations director and controller, regional business manager, and more.  

 He is a graduate of Rockland Community College where he received his associate of Applied Science in Accounting. He is also the proud recipient of both the Special Fish Award and the Keven Iles Award for work excellence.

J. Tyler Brawner – Vice President Of Investments

Tyler joined Maplewood Senior Living in 2018 and oversees the financial analysis and pro forma underwriting of all new acquisitions and development projects. He manages the ongoing financial budgeting and forecasting for Maplewood Senior Living and its existing senior living communities. Tyler began his career as an investment banker with Bank of America Securities and CS Capital Advisors, where he advised on nearly $40 billion of M&A and capital markets transactions, primarily in the senior housing, long-term care, and healthcare real estate sectors. 

He is a graduate of Yale University, where he earned a Bachelor of Arts in Economics and Political Science and played on the varsity lacrosse team. He currently lives in Massachusetts with his wife and two children.

James Adams – Vice President Of Real Estate Development

As vice president of Real Estate Development, James is responsible for executing real estate development projects under the direction of Maplewood’s chief investment officer. These responsibilities include all facets of Maplewood’s real estate development needs including design, permitting, construction and analysis to ensure the financial feasibility and operational success of Maplewood’s real estate development projects. In this capacity, James is also responsible for internal business systems and project controls required to mitigate potential risks to approved budgets and schedules, as well as associated reporting requirements to both internal and external stakeholders.  

James came to Maplewood from Steiner NYC (a Brooklyn, N.Y.-based real estate developer) and holds a Master of Science Degree in Real Estate Development from Columbia University. James also spent five years with PricewaterhouseCoopers advising clients on real estate development matters related to financial analysis and project controls on billion-dollar capital projects. 

James resides with his wife and two daughters in Fairfield County, Connecticut.

Mark Weinberger – Corporate Director Of Real Estate

In his role as corporate director of Real Estate, Mark oversees the asset management and real estate branches of Maplewood. He supports the operations team on all aspects of capital projects, maintenance, housekeeping and new community openings. Mark brings 17 years of experience in several different aspects of senior housing to his role as an executive director and also brings a background in accounting and insurance.  

Since joining Maplewood, Mark has been part of the development of five projects and will be completing and opening his sixth community, the first in New Jersey, in 2021.  

Mark has been a member of the Empire State Association of Assisted Living (ESAAL) and is currently a Board Member of Argentum New York.

Tom Caprio – Director Of Information Technology

Tom joined Maplewood in 2010, and has single-handedly built the IT department. When he started, the company only had two communities. Today, he has built a successful IT support team that services 16 communities including our flagship sister brand, Inspῑr, in New York City. 

During the COVID-19 pandemic, Tom and his team moved mountains to provide technology initiatives to benefit our communities and included temi robots, iPads, Microsoft Teams, and Zoom. These kept our associates, residents and their families virtually connected.

Moriah Prasky – Corporate Director Of Sales

Moriah is an experienced sales leader with more than a decade of sales experience in the senior housing industry. During her tenure with Maplewood Senior Living, she has held a variety of regional sales positions. In her current role as corporate director of Sales, Moriah is responsible for the company’s sales force, development and monitoring of performance and accomplishment of business objectives. Moriah was instrumental in the overall occupancy success in the company’s Ohio portfolio including Maplewood at Chardon, Twinsburg and Cuyahoga Falls. 

Moriah received her Bachelor of Science in Business Administration and Management from Kent State University. 

Jessica Edward – Corporate Director Of Business Compliance

Jessica has been at Maplewood for over seven years but has been working in assisted living for over 15 years. She brings a wide breadth of experience to the team and works throughout all of our communities managing and supervising multi-sites, payroll staff, new acquisitions and development projects. Jessica also identifies relevant partnerships, acquisitions, and new business opportunities across the media, health care, data and technology landscapes that align with corporate growth goals to minimize risk throughout the organization. 

Jessica is a graduate of Southern Connecticut State University where she received her Bachelor of Science with a concentration in Accounting. She received her Master of Business Administration in Finance from Post University. She is the proud mother of twins (a boy and a girl).

Contact Us

475-259-3252

1 Gorham Island

Westport, CT 06880


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