Advisory Board

John Bissell plain background

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 Chessloff plain background

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.

Jason Cuyler plain background

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 plain background

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 plain background

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 plain background

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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Director of Marketing

Mill Town is a community investment platform 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 make the Berkshires a better place to live, by expanding and improving the quality and quantity of opportunities to live, work, and play in the region. We work collaboratively to improve our community and region by investing in valuable projects, building connections, and empowering entrepreneurs and community organizations.

Mill Town is seeking an experienced and dynamic individual to join our team as a Director of Marketing. In this role, you will collaborate closely with the CEO, Brand Marketing Manager, operating GM’s, and business-unit marketing teams and agencies. As a key team member, you will play a vital role in executing marketing strategies in line with business objectives. This role will primarily focus on the marketing and revenue growth of our wholly-owned operating businesses, including Bousquet Mountain, Bousquet Sport, Camp Arrow Wood, The Gateways Inn, The Central Inn & Suites, and Blueprint Property Group. Our ideal candidate has an extensive marketing background and work experience managing a variety of engagements and projects end-to-end, including digital marketing, PR, events, and paid advertising.


  • Evaluate marketing strategies, tactics, collateral, and prior campaigns for effectiveness and ROI
  • Create and expand marketing strategies and plans for operating businesses including Bousquet Mountain, Bousquet Sport, Gateways Inn, Camp Arrow Wood, Blueprint Property Group, and The Central Inn & Suites
  • Design, plan, and execute effective marketing campaigns in line with the plan
  • Determine and implement key reporting metrics to measure campaign effectiveness.
  • Build brand awareness and generate innovative ideas to promote brands/products.
  • Create content strategies based on business objectives, category focus, and audience segments across all channels (online/offline/social)
  • Design and coordinate promotional campaigns, PR, and other marketing efforts across print & digital channels
  • Maintain a consistent view of marketing ROI and KPIs
  • Develop a marketing strategy for Mill Town Capital and Mill Town Foundation
  • Manage and review the marketing budget for all entities
  • Keep updated on market trends & competitor strategies
  • Provide oversight, guidance, support, and collaboration to Brand Marketing Manager
  • Support programming creation and marketing at the business unit level


  • You have a degree in Marketing, Business Administration, or a related field.
  • You have prior experience in a similar role.
  • You have deep knowledge of marketing, including brand marketing, PR, content management, digital marketing & performance marketing, and marketing analytics
  • You have excellent written & verbal communication skills and are comfortable dealing with the media.
  • Knowledge of SEO and digital marketing strategies and analytics
  • You are adept at building relationships, liaising with multiple stakeholders, and thrive in matrix environments.
  • You are a strong leader who has built, scaled, and led high-performing marketing teams.
  • You are a strategic thinker & problem solver with the ability to be hands-on.
  • You are comfortable with ambiguity and leading efforts with minimal direction

Compensation and benefits package based on experience and qualifications.

How to Apply:

Candidates can submit resumes to

Candidates can submit resumes to