

DPI Community Coffee Chat: How to Build a Successful Financial Wellness Toolkit
October 21, 2026Downtown Pittsfield, Inc. (DPI), Greylock Federal Credit Union, and 1Berkshire will host a DPI Community Coffee Chat on Wednesday, October 21, from 8 to 9:30 am, at the Downtown Pittsfield, Inc. (DPI) Conference Room at 431 North Street in Pittsfield. This is the fifth in an ongoing series of DPI Community Coffee Chats downtown open to representatives from small businesses and nonprofits in Pittsfield and Berkshire County. This is a drop-in event, and coffee and a light breakfast by AURA Coffee and Cocktails will be provided.
October 21st’s Chat Topic is How to Build a Successful Personal and Business Financial Wellness Toolkit. This informal drop-in session will feature two speakers from Greylock Federal Credit Union: Cindy Shogry-Raimer and Chris Barry.
“You don’t need to be a financial expert to run a successful business,” says Barry. “Know your numbers, have a plan, and you’ll be in a much better position to make good decisions when opportunities or challenges come your way.”
Shogry-Raimer, VP Director of Community Development, has 40 years of expertise in the financial industry and holds an MBA. She is a Certified Credit Union Financial Counselor and a former business owner. Additionally, Shogry-Raimer serves as the Treasurer of Mass Hire and PCTV boards.
Barry, Vice President, Business Banking Officer II, has been with Greylock 20 years and specializes in supporting existing and new businesses with business development, commercial loan origination, and the creation/management of new products, services, and classes. In addition to his professional role, Barry serves on the board of directors for the Berkshire Family YMCA, volunteers with the Entrepreneurship for All (EforAll) initiative, and is actively involved with Berkshire Agriculture Ventures.
This event is free and open to local business owners, organizations, and community members.
Registration for DPI Community Coffee Chats is not required but is appreciated. The registration deadline is Tuesday, October 20 at 12 pm. Registration is available at downtownpittsfield.com. (Direct link: https://forms.gle/j6dmPxBo5mxNECKm9)


