From Major Gifts to Legacy Giving: Real Fundraising Strategies

What does it really take to build sustainable donor relationships and confidently talk about planned giving?

In this episode of The Focused Fundraiser, host Rob Burke sits down with Rachel Gitner, Director of Advancement at Serendipity Center, to unpack what works in fundraising across large institutions and small nonprofits.

Rachel shares practical lessons from her journey—from classical singer to leading development efforts in healthcare, education, and mental health nonprofits. Together, they dive into donor trust, relationship-building, planned giving conversations, and how fundraisers can use systems (and AI) to stay focused and effective.

Whether you’re new to fundraising or leading development strategy, this episode is packed with real-world advice you can use today.

🎧 Topics include:

• How donor relationships actually grow over time
• Making planned giving feel natural (not scary)
• Large vs. small nonprofit fundraising strategies
• Using donor databases and AI effectively
• The single most important thing fundraisers should do today

CHAPTERS

00:22 – Rachel’s path into nonprofit fundraising

02:18 – What skills translate across nonprofit sectors

03:22 – Fundraising at large vs. small organizations

05:44 – Wearing many hats vs. specialization

05:59 – Turning local relationships into long-term donors

08:53 – Tracking donor conversations and follow-ups

10:24 – Using AI and donor databases effectively

11:19 – How to talk about planned giving with confidence

14:12 – One thing every fundraiser should do today