Trust the Process: Making the Internal Case for Planned Gicing (Even in an AI World)

  • January 14, 2026
  • 12:00 PM - 1:30 PM
  • PSA Financial [11311 McCormick Rd., Ste 500, Hunt Valley, MD 21031 - Potomac Room]

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Explore how nonprofit leaders can champion planned giving as a cornerstone of long-term mission sustainability. When we talk about marketing planned gifts, we usually think about donor-facing materials - brochures, emails, videos. But the truthh is, the most important marketing we do is internal. Before donors believe it's possible to leave a legacy, our colleagues and leaders need to believe it's essential. Internal marketing creates alignment and confidence; external marketing creates action. 

This session guides participants in framing planned giving as both a strategic and deeply human endeavor- one rooted in trust, empathy, and shared purpose. Amid rapid advances in artificial intelligence, the discussion emphasizes that authentic storytelling, personal connection, and patient cultivation remain irreplaceable. Attendees will leave equipped with practical strategies to secure organizational buy-in for planned giving, understanding ways to communicate its long-term value to leadership and colleagues. 

Session Goals

  1. Articulate the Case for Planned Giving: Help participants understand how to position planned giving as an essential, mission-driven opportunity that strengthens long-term sustainability. 
  2. Emphasize Human Connection in an AI World: Explore how authentic storytelling, empathy, and relationship building remain irreplaceable - even as AI transforms communication and data management. 
  3. Reinforce the Long-Game Mindset: Encourage patience and persistence in cultivating donors, recognizing that meaningful relationships and legacy gifts develop through steady trust and shared purpose. 

Featured Speakers

Heather Culp

Senior Vice President, Senior Associate Dean, and Chief Philanthropy Officer for University of Maryland Medicine 

Heather Culp is Senior Vice President, Senior Associate Dean, and Chief Philanthropy Officer for University of Maryland Medicine - a strategic partnership in fundraising between the University of Maryland School of Medicine (UMSOM) and the University of Maryland Medical Center (UMMC). She provides strategic guidance and vision for the fundraising efforts of UMMC Downtown and Midtown Campuses, UMSOM, and the University of Maryland Rehabilitation & Orthopedic Institute. Heather also serves as Executive Director of the University of Maryland Medicine Foundation (UMMF).

A C-suite executive with broad expertise in academic medicine and institutional advancement, Heather leads a 39-member team responsible for driving philanthropic investment in biomedical research, medical education, and patient-centered care. At UMMF, she oversees more than $110M in foundation assets, ensuring donor intent is honored through sound investment strategy and long-term alignment with institutional goals.

Heather's experience spans grateful patient fundraising as well as alumni engagement across undergraduate and graduate institutions. Over the course of her career, Heather has driven philanthropic efforts resulting in more than half a billion dollars raised for transformative healthcare and education initiatives. Before transitioning to philanthropy, Heather practiced law in both commercial litigation and estate planning.

 Ann Kolakowski, CAP, CFRE 

Director of Gift Planning Services for the University System of Maryland 

Ann Kolakowski is the Director of Gift Planning Services for the University System of Maryland, where she helps 12 campuses strengthen their approach to legacy giving through strategy, coaching, and professional development. She believes planned giving should be a joyful, transformative experience - for donors and organizations alike.

Before joining the University System in 2022, Ann held roles in planned and major gifts for the Humane Society of the United States, Towson University, and Johns Hopkins University. She also draws on a communications background that includes editing Goucher College's alumni magazine and leading communications efforts for independent schools in Philadelphia and Boston. 

Ann hold the Chartered Advisor in Philanthropy (CAP) and Certified Fund Raising Executive (CFRE) credentials, and she's a past president of the National Capital Gift Planning Council. Through her consulting practice, Akorn Consulting Group, she supports small and mid-sized nonprofits in launching and growing their planned giving programs. 


Rebecca Rothey, CFRE, CAP, AEP, IPA 

Senior Advisor: Greater Washington Community Foundation

Rebecca Rothey, CFRE, CAP, AEP, IPA is an experienced speaker and trainer in philanthropic advising and charitable gift planning. She provides the technical information that advisors need to work with clients and fundraisers, and that development professionals need to work with donors and their advisors. 

Her time as Director of Major and Planned Giving at the Baltimore Community Foundation from 2012 to 2015 ignited her passion for community foundations and their role in helping donors give back to their communities. From 2016 - 2022, she served as Chief Philanthropy Officer at the Greater Washington Community Foundation and now serves as Senior Advisor. Her Baltimore experience also includes serving as a Director of Gift Planning at The Johns Hopkins University and Medicine and Director of Planned and Principal Gifts at Catholic Charities of Baltimore. She began her career in gift planning at the American Red Cross of Central Maryland as Manager of Major and Planned Gifts. 

Rebecca serves on the editorial advisory board of Planned Giving Today. Sher served on the board of the Baltimore Estate Planning Council, is a past president of the Chesapeake Planning Giving Council, and remains an active member of the Washington,DC and other local Estate Planning Councils. 

Registration

Member - $50 

Non-member - $75 

Event Sponsor - $500  [1-2 minutes of air time before the presentation and has a flyer at the registration table for distribution to each participant.]


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