Beyond Swag: Strategic Gifting and Emotional Loyalty for Associations

In this episode of The Association Insights Podcast, host Colleen Gallagher sits down with Jamie Shibley, Co-Founder & CEO of The Expressory, to talk about how thoughtful appreciation can become a real strategy for retention, sponsorship loyalty, and long-term trust—not just a year-end “nice to have.” Drawing on her roots in her grandfather’s relationship-driven flower shop and years in corporate and e-commerce, Jamie shares how associations can use simple, intentional touchpoints to make members, sponsors, and donors feel genuinely seen.

🎧 Whether you’re behind on holiday planning, rethinking how you thank sponsors and donors, or looking for new ways to support member renewals in 2026, this conversation will help you move beyond generic swag to meaningful, strategic engagement.

Key Highlights

Holiday Triage Without the Panic: Why it’s not “too late” in late November—and how to use New Year’s or other moments as powerful appreciation windows.

Donors & Sponsors as Long-Term Partners: Ideas for gifts and messages that reflect their impact and values, instead of one-off branded items.

Member Renewal with Heart: How to use mailed touchpoints, stories of impact, and small gestures to support renewal and year-round engagement.

Personalization at Scale: Ways to make appreciation feel personal using shared challenges, goals, and themes—without custom gifting for thousands.

Measuring the ROI of Appreciation: Practical ways to track retention, referrals, and conversations sparked by strategic gifting.

🎧 Tune in for a practical, encouraging roadmap to investing in relationships—not just technology—in the year ahead letting you turn appreciation into a strategic lever for member, sponsor, and donor loyalty—all year long.

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Coming Soon: In December, we’re launching our Big Ideas & Trends Series, sitting down with association CEOs and senior leaders to explore the shifts, strategies, and bold bets that will shape associations heading into 2026. Stay tuned!