Advisory Board

John Bissell

President + CEO of Greylock Federal Credit Union

John has served as the President/CEO of Grey- lock Federal Credit Union since 2015. During that time, John has led the $1.6 billion organiza- tion toward becoming Low Income Designated (LID), CDFI certified, and a Juntos Avanzamos credit union.


He joined Greylock in 2003 as the VP of Marketing. Bissell earned his Bachelor’s Degree from Amherst College, graduated from the New England School for Financial Studies program at Babson College, and earned an MBA from the University of Massachusetts, Amherst. In 2022 he was elected to the Board of the Afri- can-American Credit Union Coalition (AACUC).


John also serves on the Advocacy Committee for the Cooperative Credit Union Association. He is a member of the MA Business Coalition for Early Childhood Education; serves on the MA Business Roundtable Board where he par- ticipates on the DEI Task Force; serves as Vice Chair for the Board of Directors for Berkshire Health Systems where he chairs the Audit Com- mittee; and serves on the 1Berkshire Alliance Board of Directors. He lives in Pittsfield with his wife Melissa and has three children.

JD Chesloff

President + CEO of the Massachusetts Business Roundtable

As President & CEO, JD is responsible for develop- ing and implementing the Roundtable’s agenda on public policy matters, and works collaboratively with opinion leaders, policy makers and other stake- holders in pursuit of its mission to make Massachu- setts the most desirable place to live, work and do business and ensure access to a robust, diverse and talented workforce that enhances the Common- wealth’s competitiveness in a global economy.

JD has worked in and around Beacon Hill for more than 30 years. In the Legislature, he was the Chief of Staff to the House Committee on Commerce and La- bor, and was the education issues analyst and Dep- uty Budget Director for the House Committee on Ways and Means. After working as both a budget analyst and Assistant to the President at the Uni- versity of Massachusetts, JD worked as the Legisla tive Director for State Treasurer Shannon O’Brien and then as Issues Director for the O’Brien-Gabrieli gubernatorial campaign in 2002.

He joined MBR in 2004 after serving as Legislative/ Issues Director for the Early Education for All (EEA) Campaign, where he was responsible for developing and driving legislative support for EEA’s legislation and agenda which included the creation of the Mas- sachusetts Board and Department of Early Educa- tion and Care. He served on the Board for 10 years, 5 as Chairman.

JD serves on the Boards of Lever, the Blue Cross Blue Shield Foundation, and Science from Scientists. He also is on the Advisory Boards of ReadyNation and CEO Action for Racial Equity.

Jayson Cuyler

Executive Director, Second Street Second Chances

Jason Cuyler is serving as Executive Director of the Second Street Second Chances (“2nd Street”) program. 2nd Street provides wrap around reentry services to formerly incarcerated individuals returning to Berkshire County. A 23-year employee of the Berkshire County Sheriff’s Office, Jason was previously a Case Management Coordinator for the Berkshire County House of Correction. In that role, he oversaw the daily operations of his team’s duties and responsibilities, which included, but were not limited to: administering initial screenings and questionnaires, establishing and maintaining counseling relationships with clients, assisting clients with post release co- ordination of services, assessing and analyzing Information for the purpose of developing individualized treatment plans, addressing both institutional and community concerns and helping clients to establish and maintain relations with community agencies.

In addition to Jason’s primary duties and responsibilities, he serves on the Berkshire County Domestic Violence High Risk Team, the Christian Center, and Hillcrest Educational Centers’ Board of Directors, and the Berkshire Community College Board of Trustees. He recently completed his six-year term limit on the Berkshire United Way Board of Directors. Jason received his Bachelor’s Degree in Sociology. and a Certificate in the field of Criminology. from the University of Massachusetts, Amherst. He is a Massachusetts Licensed Social Worker.

Ben Downing

Vice President of the Public Affairs at the Engine
Prior to joining The Engine, Ben was Vice Presi- dent for New Market Development at Nexamp, a veteran-founded, Boston-based clean energy company. There he led the firm’s strategic de- velopment efforts across growing geographies and the firm’s entry into the energy storage market. Prior to this, Ben represented the state’s largest Senate district while serving as State Senator for 52 communities in Western Massachusetts. Ben received a BA in political science from Providence College and an MA from Tufts University.

Ellen Kennedy

President, Berkshire Community College

In 2012, Ellen Kennedy was named the seventh President of Berkshire Community College (BCC), the first community college in Massachusetts. Under Kennedy’s leadership, BCC completed a $34 million renovation of its main classroom buildings, walkways and roadways; installed the Gene Dellea Community Turf Field while addressing environmental issues; secured funding and oversaw the construction of a One Stop Enrollment Center; developed and implemented a five-year strategic plan with planning for the 2022-2027 plan underway; and garnered nearly $21 million in grant funding. including a $1.9 million Title III Strengthening Institutions and renewals of TRIO Grants from the U.S. Department of Education.

Previously, Kennedy served as BCC’s Vice Pres ident for Administration and Finance and Chief Financial Officer. Prior to joining the College, she served as the Interim Chief Operating Of- ficer of National Patient Safety Foundation, the Director of Development at WFCR – Public Radio for Western New England, the Chief Advancement Officer for Massachusetts College of Liberal Arts (MCLA) and President of the MCLA Foundation. She began her career in Ad- ministration and Finance at North Adams State College, where she was actively engaged in changes to the College’s mission, name, mascot, and facilities.

Ellen holds a BS in Business Administration from MCLA, formerly North Adams State College, an MBA from the University of Massachusetts – Amherst, an MPA from the Kennedy School of Government at Harvard University, and an Ed.D. from Northeastern University.

Caitlin Pemble

Head of the Living Balance Sheet, Guardian Life Insurance

Caitlin’s ability to see connections across organizations and stakeholders combined with her desire for diverse leadership experiences led Caitlin to her current role leading all facets of Guardian’s proprietary financial planning platform, The Living Balance Sheet® (LBS). In less than 3 years leading LBS, Caitlin has brought her consumer-centric approach and revamped financial ad- visor training, implemented robust analytics, increased advisor productivity, and led the team through the design, build, and launch of a mobile app for their over 450,000 clients. A consistent builder and leader of high performing teams, Caitlin has led nationwide teams since 2018.

Past experiences include attracting and developing sales leaders, including onboarding of merged and acquired firms, multicultural market development, and client acquisition and program management for Mass – Mutual’s first integrated annual and corporate social responsibility report.

Caitlin served as an AmeriCorps volunteer from 2003-2005 as a preschool teacher, an experience that affirmed her commitment and passion for early childhood education and inspired her move from direct teaching to early childhood advocacy. Caitlin is a current Trustee of the Berkshire Museum and a member of the Berkshire Life Charitable Foundation. She previously served as a Board member for the Alumnae Association of Smith College and The Gladys Allen Brigham Community Center. She holds the Chartered Leadership Fellow® from The American College, an MPA from Westfield State University, certifications from Women Unlimited and the Boston College Carroll School of Management and completed her undergraduate studies at Smith College.

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Administrative Assistant

Blueprint Property Group is a Mill Town company. Blueprint provides property management services throughout Berkshire County.


Mill Town is a community investment group based in Pittsfield, Massachusetts, in the heart of the Berkshires. We focus on improving our region through impactful business investments, visible real estate projects, and broad community development efforts. 

Our Mission:

To expand and improve the quality of life in the Berkshires. We work collaboratively to improve our community and region by investing in valuable projects, building connections, and empowering entrepreneurs and community organizations.

Job Overview:

Blueprint Property Group is seeking an experienced Administrative Assistant to help our property management team. The right candidate will be experienced in an office environment. Experience in customer service is a must. In addition, the right candidate will be punctual, dependable, work well as a team or independently. This is a full-time, year around position with medical, dental and PTO time.

Job Responsibilities:

  • Phone and Office Support: Handle a high volume of phone calls and provide exceptional customer service to clients and tenants.
  • Office Environment: Thrive in a fast-paced office setting, assisting with administrative tasks and maintaining office organization.
  • Customer Service: Deliver top-notch customer service, ensuring clients and visitors have a positive experience.
  • Punctuality: Consistently arrive on time and manage daily tasks efficiently.
  • Teamwork: Collaborate effectively with the property management team and work independently when necessary.
  • Phone and In-Person Interaction: Answer phone inquiries, schedule appointments, and greet visitors in a professional manner.
  • Accounts Receivable and Accounts Payable: Assist in managing financial transactions, including invoicing, processing payments, and maintaining accurate records.


  • Previous experience in a similar administrative role, preferably in a busy office environment.
  • Exceptional customer service skills and a friendly, professional demeanor.
  • Strong organizational skills and attention to detail.
  • Ability to work both as a team player and independently, managing multiple tasks effectively.
  • Knowledge of accounts receivable and accounts payable processes is a significant advantage.
  • Excellent written and verbal communication skills.

How to Apply:

If you are a dedicated and experienced Administrative Assistant looking to join a thriving property management team, please submit your resume and a cover letter detailing your relevant qualifications and why you are an ideal candidate for this position.

To apply, please send your resume to or attach your resume on the form below: