Hi, I’m Zach Dierolf — founder of Trailhead Strategic Leadership Coaching.I help business owners and executive teams reclaim momentum, streamline operations, and lead with clarity. My specialty is working with companies that have grown past the startup phase but now find themselves stuck—plateaued, overwhelmed, or stretched thin by complexity.I’ve walked this path myself. I’ve built, led, and advised teams across multiple industries, and I know how frustrating it can be when passion is high but progress stalls. Through hands-on coaching, strategic insight, and a systems-first approach, I help leaders get unstuck and build companies that run smoother, scale smarter, and stay aligned with their original vision.I believe every company reaches a crossroads. The question is: will you keep grinding… or find your Trailhead and start the next climb?Let’s build the next version of your business—together.


If you're ready to stop winging it and start scaling with clarity and confidence, book a call now. Let's talk goals, bottlenecks, and the path forward.We only take a few clients per quarter, don't wait!