I'm the founder of Caldwell Leadership. I write here about leadership, culture, and the operating systems that hold them together—especially now, as small teams figure out how to lead, collaborate, and decide alongside AI.

Two decades leading creative and technology teams across North America. Two businesses of my own. Eight years leading design at a small app development studio whose clients included Google and Microsoft. A stint at Shopify where my team grew small-business funding deployment from $87.8M to $162.4M.

What people hire me for is rarely what they realize they needed. They hire me to fix the work. What changes is how the work is being thought about.

I design human-centered operating systems where leadership, culture, and innovation compound—instead of competing for what's left of your attention. Mostly with founder-led teams scaling leadership before they've built a full executive bench.

If you're a leader carrying everything alone, find me at Caldwell Leadership.