617.431.1880 | Careers

Leadership Team

Jake Quigley, Executive Director of Waterstone at the Circle.

Jake Quigley

Executive Director

With more than 12 years in the senior living industry, Jake truly understands what active seniors want in an independent senior living experience and knows just how to inspire our team to go above and beyond to deliver an exceptional experience for our residents. As Executive Director, Jake is responsible for overseeing daily operations and ensuring our residents and their families are being treated with the high levels of customer service that our senior living community in Chestnut Hill is known for.

Jake has served in various Executive Director roles prior to joining Waterstone at the Circle’s team. For the past several years, Jake has filled the Executive Director role for other senior living communities throughout Boston, Chestnut Hill and Newton. He simultaneously works as an Adjunct Professor for Regis College in Weston, Massachusetts, where he mentors and instructs students on the subjects of Gerontology, Health Care Management and Public & Health Care Policy.

Jake has a genuine love of education and a deep understanding of the needs of active seniors. His expert knowledge and positive leadership approach inspire our team to provide the absolute best service to our residents, making Waterstone at the Circle the Boston senior living community of choice for independent seniors.

Jake earned his Bachelor of Science in Family Studies and Human Services and has also earned a Master's of Science in Gerontology, Master's of Science in Community Development all from Kansas State University, and a Doctorate in Law and Public Policy from Northeastern University. Jake is also a veteran of the United States Navy.



Scott Weissman, Assistant Executive Director at Waterstone at the Circle

Scott Weissman

Assistant Executive Director

Scott brings over 12 years of experience in the senior living industry, with a background as a Life Enrichment Director and Director of Business Administration, including for Waterstone at the Circle. With the skills he has acquired over the years, Scott works alongside Executive Director Jake Quigley to oversee the daily operations of the community.

He is dedicated to supporting the entire Waterstone at the Circle team in providing outstanding hospitality and service to all residents. He also takes great pride in putting team members in positions where they can be successful and experience personal and professional growth. His leadership and passion for helping others is evident in everything he does.

Scott greatly enjoys the personal interactions and relationships that he has fostered since joining Waterstone at the Circle and looks forward to building connections with new residents and the greater community.



Kathleen Winn, Senior Advisor

Kathleen Winn

Senior Advisor

With over 20 years of sales and marketing experience, and over 10 of them being focused in senior living, Kathleen has the expertise and knowledge necessary to connect area seniors with the urban lifestyle, amenities and culture that Waterstone at the Circle has to offer. Her upbeat, dynamic personality allows her to build relationships and deliver on the high level of customer service that residents at The Circle expect.

Kathleen enjoys being part of the Waterstone team and providing area seniors and their families with resources, support and information to ensure a smooth and positive senior living experience. She says caring for others, and especially seniors, is simply in her nature, as she comes from a family with many members in the service and senior living industries.

Kathleen was born and raised in Massachusetts and, although she has lived in Los Angeles and North Carolina, she has come back home to Boston with her husband Kevin and her Chihuahua, Murphy – her very own beloved senior dog.

Michelle Collins, Life Enrichment Director

Michelle Collins

Life Enrichment Director

Michelle Collins injects enthusiasm, professionalism and creative thinking into all that she does to help residents be active and engaged. For the majority of her career, she was an educator in higher education and as Life Enrichment Director, her experience and knowledge of the importance of social and intellectual engagement helps residents live to the fullest each day.

Michelle has worked for almost thirty years in higher education as a basketball coach, leader, mentor and educator. Most recently, she has worked as part of the life enrichment team at one of our sister communities, creating vibrant and engaging programming for residents. Michelle’s passion for helping seniors stay active as well as her ability to connect with everyone she meets makes her perfectly matched for this role.

Michelle earned her bachelor’s degree from Siena College and her master’s degree from Concordia University Irvine.

Jason King Senior Dining Service Director / Executive Chef

Jason King

Senior Dining Service Director / Executive Chef

Jason King, our Senior Dining Services Director and Executive Chef has been formally trained under several James Beard award winners at two renowned Boston restaurants – Abe & Louie’s and The Tuscan Grill – prior to joining the team at Waterstone at the Circle. 

Jason says his love of food developed while cooking with his family, which he has carried over to Waterstone at the Circle. Each day he prepares menus, incorporates residents’ feedback, cooks and uses his talents to make dining a pleasure at our community.

He enjoys creating and preparing food for our residents and team, and often feels as though he is cooking for family. He states that one of his greatest rewards is when someone tells him how much they truly enjoy something he and his team have prepared.