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When: Thursday, October 22nd (4:00-5:30 pm)
Where: In Person, Abandoned Building Brewery, 142 Pleasant St #103a, Easthampton, MA 01027 - Register Here
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With the fundraising environment constantly evolving, so too must the campaigns that benefit our organizations. This session will explore how to recast traditional guidelines to create and execute a successful fundraising campaign for today’s world. With more than twenty years in the field, Diane Dukette and her team have run a bevy of successful campaigns: comprehensive, capital, and, soon, a board-approved legacy campaign. Looking at these experiences, what traditional campaign guidelines are still relevant? What has changed? We’ll dive deep into real-life examples to compare the “perfect” campaign of old with a modern campaign adapted to today’s challenges. This session combines presentation, comparative analysis, and a “what would you do” interactive case study discussion so that participants walk away with tools and examples to help you stay nimble in the ever-changing landscape of non-profit fundraising. Diane Dukette is the Chief Development Officer at Cooley Dickinson Hospital, a Mass General Brigham affiliate, in Northampton MA, where she is honored to lead one of the finest development teams possible. Their efforts have strengthened community health care with a series of successful campaigns: comprehensive, capital, programmatic. The most recent campaign, Transforming Emergency Care, raised $16M towards the $26M Emergency Department expansion, doubling the original $8M goal. They are planning a legacy campaign to launch in early 2027. Previously, Diane was Vice President, Fund Development at the Sisters of Providence Health System, in Springfield MA, where she worked with volunteers and staff to execute the $11.3M Capital Campaign for the Sister Caritas Cancer Center in two years. Diane also served as Assistant Vice Chancellor of Advancement and Executive Director of Development at the University of Massachusetts Amherst, where she led a team of fundraisers to close the University’s first-ever comprehensive campaign, one year early, and at $130.7M, $5.7M over goal. During her tenure she was an integral member of the team that secured the gift to name the Isenberg School of Management. Diane holds an MBA from the University of Massachusetts Amherst and a BA from Smith College. She serves on the West Springfield Public Library Board of Trustees; former volunteer roles include director, Alumnae Association of Smith College Board, and board member for both AFP and Women in Philanthropy western Mass chapters. She has presented at AFP W MA, AFP Int'l, NEAHP, AHP Int’l, and CASE/NAIS, and co-taught AFP’s Fundamentals of Fundraising Course. She is a recipient of the Outstanding Professional Fundraising Executive Award by the Association of Fundraising Professionals, Western Massachusetts Chapter. Diane has over twenty-five years of development experience during which she has consistently built comprehensive fundraising programs, exceeded financial goals to support her organizations’ missions, and fostered the next generation of fundraisers through staff and volunteer development. During her career, Diane and her colleagues secured two challenge grants from the prestigious Kresge Foundation, which required the recipient organization to create a robust fundraising program that is sustainable post-campaign. In a field that is based on relationships, she is especially proud that the length of tenure of her development staff averages 10.6 yrs.When: Thursday, November 12th (4:00-5:00 pm)
Where: In Person at New City Brewery - 180 Pleasant Street, Rear, Easthampton, MA 01027 (Registration Coming Soon)
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Learning Lab RoundtablesJoin our email list to receive notifications on upcoming meetings and events!
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When: Tuesday, June 16th (12:00-1:00 pm)
Where: Virtual
Presenter: Stephanie Flaherty, Director, Leadership Annual Giving & Pipeline Development at UMass Amherst Foundation
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This presentation equips fundraising professionals with a practical framework for identifying and cultivating future major gift donors within their own organizations or institutions. By walking through the structure and strategy of UMass Amherst Foundation's Leadership Annual Giving (LAG) Program, attendees will learn how to build and manage a program that will serve as a bridge between traditional annual giving efforts and major gift fundraising. Attendees will walk away with a replicable moves management framework, personalized engagement strategies, and a compelling data-driven case for why investing in mid-level donors is one of the most effective ways to grow a major gifts pipeline.Stephanie Flaherty is a seasoned fundraising and development professional with nearly two decades of experience building meaningful relationships between donors and the institutions they care about. Her work has primarily been in higher education — uniting a consistent passion for philanthropy with an exceptional ability to cultivate and convert donor interest into lasting investment.
Currently serving as Director of Leadership Annual Giving & Pipeline Development at the UMass Amherst Foundation, Stephanie leads strategies that identify and nurture high-potential donors, bridging the critical gap between annual giving and major gift fundraising.
Between her two stints fundraising on behalf of UMass Amherst, Stephanie broadened her expertise as Director of the Amherst Fund at Amherst College, a Development Officer at Cooley Dickinson Hospital, and a Major Gift Officer at Keene State College — each role deepening her fluency in donor stewardship, pipeline strategy, and the unique cultures of advancement across institutional types.
May: Meet the Funders Panel
When: Thursday, May 28th (4:00-5:30 pm with networking) Where: In Person at New City Brewery - 180 Pleasant Street, Rear, Easthampton, MA 01027 Read moreModerated by Megan Burke, President/CEO, Community Foundation of Western MassachusettsJoin Women in Philanthropy for an engaging and timely conversation with regional philanthropic leaders as we explore the evolving landscape of funding, community investment, and nonprofit partnership. Meet the Funders will bring together leaders from the corporate, foundation, and community giving sectors to share insight into current funding priorities, emerging community needs, and what meaningful collaboration with nonprofits looks like in today’s climate. Panelists will discuss trends they are seeing across the sector, how organizations can build authentic and lasting relationships with funders, and the important role philanthropy plays in strengthening and sustaining our communities during uncertain times. Attendees will also have the opportunity to hear directly from funders about the values and strategies shaping their work moving forward.
We are honored to welcome the following panelists:
Whether you are a nonprofit professional, donor, volunteer, board member, or community advocate, this conversation will offer valuable perspective, practical insight, and an opportunity to deepen connections across our region’s philanthropic community.
April: No Crystal Ball Required: Supporters Share What Matters Most
When: Wednesday, April 29th (12:00-1:00 pm) Where: Virtual via Zoom Read moreJoin us for a panel discussion with local supporters as they share the experiences that shape their giving. Hear how their motivations have evolved over time and which interactions make them feel valued, celebrated, and part of something bigger. Reflect on your own experiences - and how listening more closely can help shape deeper connections with your organization’s supporters. |
When: Tuesday, September 15th (12:00-1:00 pm)
Where: Virtual
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Presenter: Dana Gillette, Director of Gift Planning, Mount Holyoke College
Program Description:
Many donors and financial advisors overlook retirement accounts as a primary vehicle for philanthropy, missing out on exceptional tax and timing advantages. This session provides fundraisers of all experience levels with a clear breakdown of the mechanics, eligibility criteria, and simple setup processes for outright gifts and bequest designations. Presenter Dana Gillette will highlight common blind spots that often prevent donors from leveraging these high-value assets. Gain actionable insights to spot hidden giving opportunities and help your supporters create a powerful legacy with ease.
Biography:
Dana Gillette serves as Director of Gift Planning at Mount Holyoke College, where she works with alums and friends who wish to make the College part of their legacy. Her expertise includes life income gifts, such as charitable trusts and charitable gift annuities, as well as bequests, beneficiary designations, and complex outright gifts. A dedicated development professional, volunteer, and donor, Dana brings more than two decades of leadership experience in the nonprofit sector. She is a passionate advocate for philanthropy's power to transform lives and strengthen communities, with expertise spanning gift planning, fundraising, and strategic communications.
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