Designing High-Engagement Executive Communities for Enterprise CS
Designed for Senior Customer Success Directors and VPs at enterprise SaaS organizations responsible for post-sale executive relationships to spark real collaboration and high-energy learning.
A 90-minute virtual workshop for senior CS leaders who report executive engagement is low, time is scarce, and existing community programs are transactional or underutilized. Participants feel pressure to demonstrate ROI for community investments and struggle to activate authentic peer interaction among senior client stakeholders.
The Secret Executive Wish List
Start with a rapid-fire poll: 'What do you think is the #1 thing enterprise execs secretly want from your community—beyond product updates?' Immediately reveal anonymized customer interview snippets with surprising answers (e.g., 'Unfiltered peer war stories', 'A sense of industry influence'). Participants compare their guesses to real desires.
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Why this works
This primes curiosity and corrects assumptions, setting the stage for designing with authentic motivators in mind.
Unpacking 'Too Busy': Myth vs. Reality
Display a word cloud of reasons execs give for not joining communities (e.g., 'No time', 'Not relevant', 'Too much vendor talk'). Invite a mini-debate: Which barriers are real, and which are polite smoke screens? Share a counterintuitive research tidbit: the highest-engaged execs often join the most selective, peer-driven forums.
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Why this works
Helps bust the myth that time is the only barrier and sets up solutions that address true blockers.
Uncommon Community Icebreakers
Invite everyone to submit, in chat, one unconventional icebreaker question they've used or experienced with executives (e.g., 'Describe your leadership style with a movie title'). Read out 2-3 and run a quick poll: Which would you actually use in your next executive session?
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Why this works
Fosters safe, low-pressure participation and models creative ways to spark genuine conversation among high-level participants.
Flashpoint: Community Redesign Sprint
Divide the group into breakout teams. Each team gets 10 minutes to redesign a failing exec community (case provided with low attendance, disengagement, and superficial topics). Teams must pick 2 bold changes—format, hosts, incentives, or topics—and pitch back their plan in 60 seconds.
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Why this works
Injects positive energy and competition, pushing participants to think creatively under time pressure and reinforcing design principles.
The 'Hard Trade-off' Dilemma
Present a real-world dilemma: 'An exec community member wants to discuss industry disruption—but your product team insists on showcasing a new feature. You have limited session time. What do you do?' Invite participants to choose a side in chat and defend it in 1 sentence. Then reveal how top CS leaders have navigated this with success stories.
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Why this works
Grounds discussion in authentic stakes, sparking debate and realistic solutioning.
My Executive Community Commitment
Invite each participant to write down (privately or in chat) one concrete step they’ll take in the next 30 days—whether redesigning an invitation, piloting a new format, or asking for direct executive feedback. Optionally, pair people for accountability follow-up.
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Why this works
Anchors learning in personal action, boosting transfer and commitment beyond the session.
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