Caitlin's spent 20 years scaling small businesses. She built one to exit and has worked alongside 100+ founders, helping generate north of $20M in revenue and funds raised along the way.
What you'll notice in her classes is how quickly the thing you've been dreading starts to feel doable. She's the architect of the Keystone™ Methodology, which helps teams build AI into the way they already work — so it feels like a trusted colleague, not like starting over with a stranger every time. She's spoken on this methodology internationally at Operations Nation, CHIEF, and AI education events — and trained 120+ leaders to build their own.
When she's not helping leaders embrace AI, she's with her family and her corgi.
Founder & CEO
Sawyer Middeleer is a strategic operator, agentic builder, and educator with over a decade of experience helping operating leaders get more done with technology. He has designed and shipped AI operations automations for more than 20 organizations across business services, technology, and infrastructure, and has led hands-on AI agent workshops for over 350 operations and go-to-market leaders.
Instructor