After eighteen years of building and operating founder-led companies — through growth, plateaus, pivots, and the kind of quiet crises that never make it into the highlight reel — I’ve formalized what I’ve been doing informally for most of my career.
Headlands Ops is a dedicated operational advisory practice for B2B founders in the $2M–$20M revenue range. Not a consulting firm. Not a coaching practice. A peer-level operational partnership — the kind that installs real infrastructure and stays until the machine runs without the founder holding it together.
The name comes from the Marin Headlands, a few miles from where I live and work. There’s something about that terrain — the elevation, the visibility, the sense of earned perspective — that felt right for what this practice is actually about. You climb to the vantage point first. Then you build the trail.
The practice is built around The Headlands Operating System, a five-phase methodology developed over nearly two decades of pattern recognition across founder-led businesses. It’s structured without being rigid. Proven without being generic. And designed specifically for the kind of company where the founder’s identity and the company’s identity are still, for better and worse, the same thing.
We’re now accepting new engagements. If any of this sounds familiar, the first conversation is a good place to start.