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In this first installment of a special two-part episode of Sidecar Sync, Amith and Mallory explore the future of AI-enhanced member services. Associations face growing pressure to provide seamless, 24/7 member support—competing with the personalized service of big brands. In Part 1, we break down key member service functions and how AI can revolutionize them, from automating inquiries and renewals to personalizing communication and recommendations. Plus, we introduce Izzy, a groundbreaking AI agent designed to transform association operations. Stay tuned for Part 2, where we’ll dive into real-world implementation strategies!
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🚀 Find out more about the upcoming Blue Cypress Innovation Hubs!
Washington, D.C.: https://bluecypress.io/innovation-hub-dc
Chicago: https://bluecypress.io/innovation-hub-chicago
Chapters:
00:00 - Welcome to Sidecar Sync
01:09 - Introducing AI-Enhanced Member Services
06:20 - Why AI is Critical for Modern Associations
08:08 - The Role of AI in Reducing Friction
16:55 - AI’s Task-by-Task Transformation of Member Services
18:29 - Responding to Member Inquiries with AI
28:54 - Automating Applications and Renewals
41:25 - Smarter Database Maintenance with AI
51:39 - AI-Powered Personalized Communications
57:36 - Smarter Upselling & Cross-Selling with AI
1:02:35 - Closing -- Stay Tuned for Part 2!
📅 Find out more digitalNow 2025 and register now:
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🎉 More from Today’s Sponsors:
Member Junction https://memberjunction.com/

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Amith Nagarajan is the Chairman of Blue Cypress https://BlueCypress.io, a family of purpose-driven companies and proud practitioners of Conscious Capitalism. The Blue Cypress companies focus on helping associations, non-profits, and other purpose-driven organizations achieve long-term success. Amith is also an active early-stage investor in B2B SaaS companies. He’s had the good fortune of nearly three decades of success as an entrepreneur and enjoys helping others in their journey.
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Mallory Mejias is the Manager at Sidecar, and she's passionate about creating opportunities for association professionals to learn, grow, and better serve their members using artificial intelligence. She enjoys blending creativity and innovation to produce fresh, meaningful content for the association space.
📣 Follow Mallory:
https://linkedin.com/mallorymejias