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In this milestone 75th episode of Sidecar Sync, Amith and Mallory return for part two of their deep dive into AI-enhanced member services. This second installment of AI-Enhanced Member Services shifts from ideas to action. Amith and Mallory focus on the infrastructure, mindset, and change management strategies needed to implement AI solutions within your association. You’ll hear clear advice on system integration, data platforms, and the human side of transformation—including how to reframe staff roles and build a culture of innovation. It’s a must-listen for association leaders ready to take the next step.
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📕 Download ‘Ascend 2nd Edition: Unlocking the Power of AI for Associations’ for FREE
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📅 Find out more digitalNow 2025 and register now:
https://digitalnow.sidecar.ai/
🚀 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
🛠 AI Tools and Resources Mentioned in This Episode:
ChatGPT ➡ https://openai.com/chatgpt
Google Gemini ➡ https://gemini.google
Chapters:
00:00 - Welcome to Episode 75 of Sidecar Sync
05:32 - The Three Building Blocks for AI Member Services
12:04 - In the Middle of an AMS Switch? Hit Pause
17:42 - Common Obstacles: The "Accounting" Mindset
20:44 - What to Automate First: Member Inquiries
22:05 - Change Management and the Leadership Imperative
28:32 - Culture Shifts: Asking “Why” and “Why Not?”
33:28 - Unlocking New Strategic Capacity with AI
37:45 - Culture Fit and Leading Through Transformation

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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