AI Mastermind

Lead the AI Revolution in Associations

Join an elite network of association executives who are shaping the future of the industry through artificial intelligence.

  • From Insight to Action with AI Agents: Build 10+ AI Agents in 12 months. Walk away with practical experience building and implementing organizational agents, ready to deploy within your own ecosystem. Dive in during ten monthly, online sessions where association executives build together.
  • Exclusive Leadership Circle: Collaborate with visionary association leaders exploring the latest strategies and innovations.
  • Unparalleled Access: Complimentary registration to digitalNow in the fall and Sidecar’s Innovation Hubs, for the two yearly in-person sessions.

Designed for CEOs, CxOs, and other senior leaders, the Association AI Mastermind ensures you’re equipped to lead your organization into the future with AI. Association vendors are not eligible to join the AI Mastermind.

Designed For Busy Executives

12 Monthly Sessions of Transformation

90-minute monthly sessions (longer for the two in-person sessions at digitalNow and Innovation Hub). 15–20 min pre-work with optional 45–60 minute deep dive. All sessions recorded for future use.

Apply Agents Immediately

Build real agents. Use Monday morning. Actively implement transformation.

Peer Learning

Round-robin building. Share challenges. Learn from peers.

What the CEOs are saying
"Participating in the CEO Mastermind Group has helped us begin developing strategies for utilizing AI to take advantage of emerging business opportunities and mitigate any risk the technology may present to our organization."
Steve Carey
Steve Carey
President & CEO, NTEA - The Work Truck Association
The AI CEO Mastermind was a great way to help my organization stay ahead of the curve. It was incredibly valuable to learn where things are going, where they currently stand, and how other participants are dealing with this new landscape."
Joe Skeel
Joe Skeel
Executive Director, Indiana State Bar Association
"I enjoyed participating in the AI Mastermind for CEOs over the past several months as it has helped me understand where we as association leaders need to focus our time and attention. The field of AI is evolving at warp speed, and these sessions are key to helping us stay current."
Lawrence Sloan
Lawrence Sloan, MBA, CAE, FASAE
Chief Executive Officer, AIHA
Yearly Investment
$10,000
  • Access to monthly virtual gatherings and personalized office hours
  • All access ticket to the digitalNow Conference (valued at $1,500) plus access to a Sidecar Innovation Hub, valued at $399.
  • Option to add a key executive registration for an additional $5,000

Key Benefits
VIP Experience at digitalNow

Your investment in the Association AI Mastermind Group includes registration to digitalNow, and a special in-person experience for the AI Mastermind Group. It also includes Innovation Hub registration in the spring.

Exclusive Resources, Content, and Recorded Sessions

Access recordings of all monthly sessions, along with summaries and transcripts. Our private online forum hosts exclusive content on emerging AI topics and practical implementation ideas. Review recordings of each meeting at your convenience, and if you miss a session, watch the recording and schedule a 1:1 make-up session to discuss any questions.

Come One, Come All

Leadership teams that learn together are better equipped to innovate together. If you're interested in joining the Association AI Mastermind with more than one leader from your association, you can do so for a discounted price. This inclusive approach ensures your team can learn and grow together, fostering collaboration and creating valuable connections with other participating organizations.

Frequently Asked Questions