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 2025 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 in the fall and Innovation Hub in the spring )

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

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

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, MBA, CAE, FASAE

Chief Executive Officer, AIHA

Yearly Investment

Pro-rated based on join month

$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

Get Started

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.

FAQs

Who is the Mastermind group for?

This group is for association professionals who are interested in making AI work for their association. There is no prerequisite knowledge required.

While we strongly encourage 100% attendance across the sessions, we will also be recording the sessions and making them available in the online community for replay or if someone has to miss a meeting.

Our only requirement is that you are curious and want to leverage this disruptive tech to benefit your association. Again, there is no prerequisite at all for knowledge of AI.

How are the meetings scheduled?

Monthly meetings, for 75 minutes each. 10 of the meetings are virtual, and 2 of them are in person at the digitalNow and Innovation Hub conferences.

What if I'm joining later in the year?

We're happy to pro-rate the investment based on the number of months you'll be involved with our Mastermind Group. Please note that we cannot pro-rate the cost of the digitalNow Conference ticket included in your registration.

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