When experience becomes a liability: the CEO hiring trap in sub-$100m businesses

Tim Dunn 17 Feb 2026

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A board-level perspective on contextual fit, growth mindset and leadership readiness.

 

Many boards appoint CEOs in sub-$100M businesses based on proven experience and prior tenure, yet this approach can unintentionally limit future growth.

Tim Dunn shares his insights in this article, which explores why traditional credentials alone are not always the strongest predictor of success in smaller, scaling organisations. It examines the importance of contextual fit, learning agility and leadership versatility — qualities that enable CEOs to navigate ambiguity, build capability and grow with the business. For boards, it offers a sharper framework for making one of their most critical leadership decisions with confidence.

 

View the full report below.

 

Tim Dunn

Tim Dunn

Tim Dunn is a seasoned executive search leader and former U.S. Army Officer, bringing deep expertise in identifying transformative talent for private equity-backed, middle-market businesses. As a Partner at Leathwaite, he focuses on placing CEOs, CFOs, COOs, and CROs across…

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