Blending Strategy with Heart: Jill Cancellieri Offers Reflections Upon Her Retirement

Our Director of Philanthropic Services reflects on her twelve years of service to the foundation and offers guidance to the next generation of philanthropic leaders.

By Deirdre McKenna / December 06, 2024

Jill with founding board member Alice Yoakum.
Jill with Sally Eagle, first President of BTCF.
Jennifer Dowley, BTCF president (1998-2015).
L-R: Richard Weininger, Martha McMaster,
Sheldon Evans, Gretchen Stearns Weininger.

Twelve years ago, Jill Cancellieri set her sights on joining the team at Berkshire Taconic, fueled by a love of the Berkshires and a desire to deepen and cultivate connections between philanthropy and local need. Since joining the Foundation, her contributions have been a building block upon which Berkshire Taconic has grown. She’s helped numerous donors connect their values to local causes that inspire them and that will have the greatest impact over time.  
   
Jill joined BTCF after serving in Major Gifts Officer roles at The Nature Conservancy and Save the Children in Connecticut. She remembers the moment when she knew she had made the right move to the Berkshires: Upon entering her first meeting, she noticed one empty seat and was told, “we’ve been saving this seat for you.” That warm welcome set the tone for subsequent years of collaboration with her colleagues, and years-long relationships with individual donors and their families.   
   
Jill has carefully laid the groundwork for the next generation of our foundation’s relationship managers to take the helm in the stewardship of existing funds and establishing new ones. A parting task she found especially gratifying was reviewing her portfolio of funds and matching up the perfect colleague with each of her donors. Emily Bronson, Senior Community Engagement Officer for Initiatives & Special Projects shares, “Jill provided over a decade of mentorship to me. She led with the principle of excellence in all she did and listened with incredible care to donors.”

Jill believes that building personal relationships and trust over time are at the core of success in serving donors and the community. With a deep knowledge of the unique needs of the four counties we serve, Jill has helped donors amplify the positive impact their giving has. In many cases, Jill has worked with donors to set up legacy funds that will serve the community after their passing and sees that work as a privilege and a sacred responsibility. She has taken pride in guiding donors through the process of creating a framework to ensure their choices are respected and implemented “with the specificity and generosity they intended.”

Building Connections, Looking to the Future

Jill encourages the next generation of philanthropic leaders to be mindful of the power and importance of being an active listener, both with donors and with community-based nonprofits, “Collaboration and community building are critical to becoming ‘informed champions,’ matching resources with needs, and establishing long-term trust.”

During her tenure, Jill has seen the foundation refine its strategy to have greater impact by leveraging philanthropy to address long-term, systemic challenges. Our strategic priorities emerged from an eighteen-month period of research via surveys and focus groups with local leaders, nonprofits, and donors. BTCF identified three major areas of focus to serve as a roadmap for future work: Community Engagement, Educational Access, and Economic Opportunity. Jill describes this type of ongoing collaboration with community as the “hard and patient work.”   

Kara Mikulich, Interim President of BTCF shares, “Jill’s work at BTCF over the last decade has left a lasting impact on our nonprofits, our communities, and our neighbors in need. Jill will be deeply missed by her colleagues and donors. She brought so much warmth, wisdom and wit to our work and our workplace." Emily Bronson echoes that sentiment, “It has been an honor and privilege to work with Jill.”  
   
Jill looks forward to spending more time with her family in her retirement, perfecting her skills with her “Pickle Ball Posse,” and doing some volunteering. She encourages everyone to “Keep on keepin’ on and be the light.” We wish Jill a joyful retirement filled with meaningful memories and the pride of knowing the lasting impact her work has had on our community. 

Two Local Organizations Receive Grants in Jill’s Honor

Jill’s influence will be felt for many years to come, and in recognition of her outstanding services to the foundation and her community, Berkshire Taconic Community Foundation has donated to two local organizations in her honor. Based on Jill’s recommendations, funding will support general operating expenses for Hands in Outreach, a Sheffield, Mass. organization that gives marginalized girls in Nepal access to education so they can navigate a path toward self-reliance and financial stability. Funding will also go to 18 Degrees in Pittsfield, Mass. which provides support to children and families, with a focus on early education and parenting support, as well as advocacy for foster care and adoption, family well-being and youth and community development.