I've lived the chaos of a business scaling from 50 to 150+ people, when the systems that used to work suddenly don't. That's exactly what I help with — rebuilding what's underneath so the goals you set at your offsite actually turn into what happens day to day.
Most of my clients already know the business has outgrown the systems running it. They just don't have the bandwidth to rebuild them, let alone figure out where AI actually fits and how to bring it in without breaking what's already fragile. My belief: you can't bolt AI onto a broken process and expect anything but broken AI — so I build the foundation first.
With 15+ years as a strategic operator at high-growth companies like Vistaprint, TripAdvisor, Chegg, and Hummingbird Healthcare, I've learned that a strategy is only as good as the operating system behind it. That experience across e-commerce, travel, edtech, and healthcare has shown me that execution problems look remarkably similar regardless of industry — and so do the structural solutions.
That pattern is what became the Viewpoint Stack™. After watching the same failure mode repeat across every industry I've worked in, I stopped seeing it as a series of unrelated problems and started seeing it as one system with four layers — Vision, Alignment, Clarity, and Infrastructure — each one load-bearing for the next. A strategy that looks sound on paper. A leadership team that feels aligned. An org where nobody's quite sure who owns what. Systems nobody trusts enough to run the business on. Weaken any one layer and the damage doesn't stay contained — it compounds downward into the next one. That's the lens I bring to every engagement: find the layer that's actually broken before building anything on top of it.
- Deep Systems Thinking: I don't patch the thing that broke. I figure out why it keeps breaking.
- Outcome-Obsessed: I'm not here to hand you a slide deck. I'm here to build something your team actually uses.
- Iterative Execution: I treat your org like a product — shipping changes, watching what breaks, and rebuilding instead of waiting for a perfect plan.
- AI as Architecture, Not Add-On: Most companies add an AI tool and call it done. I build AI into how the work actually happens — so it's still paying off a year from now.
Based in the Boston area, I work with a limited client roster to ensure every engagement gets my full focus as a fractional strategic operator. I embed directly within your leadership team—in your Slack, your meetings, and your reality—to connect the dots and move the business forward.