Rockwood Returns to Cleveland

There’s something fitting about bringing leaders together in Cleveland. After all, the city is built on grit, momentum, reinvention, and practical creativity. It is the kind of place where ideas turn into action.

In mid-June, Rockwood returned to downtown Cleveland for its 13th annual Leadership Summit. This year, the event welcomed portfolio company leaders, Rockwood River Guides, operating partners, speakers, and longtime friends of the firm. Together, the group spent two days focused on connection, learning, and growth.

Ideas, Connection, and Leadership in Action

To begin, our Leadership Summit opened with Wade Wyant of Redegades.AI. He shared practical insights on intelligent AI implementation and the value of identifying custom use cases. In particular, his discussion helped frame AI in a clear and useful way. It is not just a buzzword. Instead, leaders can use it thoughtfully to support better decision-making, efficiency, customer experience, and long-term growth.

 Next, Jon Colby  brought a very different kind of energy to the room. Drawing on his improv background, he led the group through a series of communication exercises. His session introduced just the right amount of structured chaos. Attendees left sharper, more connected, and laughing along the way.

Beyond the sessions, our Leadership Summit also created space for relationships to grow. At Tuesday night’s tour of the Rock & Roll Hall of Fame, one CEO shared, “My team and I started talking about the takeaways at dinner at the Rock & Roll Hall of Fame.”

Finally, Brent Robertson of Be Generative closed out the speaker lineup. He shared a thoughtful reflection on treating life as a conversation. Ultimately, his message offered a fitting final note. It also reminded everyone that leaders write the best leadership stories intentionally and collaboratively.

Looking ahead, plans are already in motion for 2027. Until then, we’ll keep Growing Together. 

Explore more: Check out Rockwood’s Leadership Library and Past Presenters

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