What Osgood Advisory Does

Most digital transformations fail not because of technology, but because nothing durable ever gets built. Strategy lives in slide decks, roadmaps stall, and organizations change language without changing capability.

Osgood Advisory exists to close that gap.

I work with leaders to turn transformation into something tangible by identifying missing or degraded organizational assets and taking ideas from zero to something real. This often happens where innovation has stalled, opportunity exists but is not yet visible, or existing structures no longer match reality.

How I Work

My work focuses on zero to one creation and early stage scale. That may involve inventing a new product, platform, or internal capability, designing the strategy, structure, and systems needed to support it, or helping leaders understand why progress feels harder than it should despite significant investment.

I typically operate at the boundary between invention and scale, where uncertainty is high, existing models break down, and clarity matters most. This is the work organizations struggle to do internally and where the greatest leverage exists.

Organizational Debt

This work is grounded in Organizational Debt, my forthcoming book and operating framework for understanding how decisions accumulate inside organizations over time.

Organizational debt builds when strategy, structure, and systems drift out of alignment, quietly limiting perception, slowing execution, and blocking innovation. I use this framework not as theory, but as a practical tool to diagnose blind spots, design durable solutions, and help organizations create the assets transformation actually requires.

Engagement Models

Engagements with Osgood Advisory vary by context and need.

Sometimes I serve as a trusted advisor to founders or executive teams navigating complex change. In other cases, I work more deeply to invent, build, and transition a new capability into the organization once it is ready for scale.

In all cases, the objective is the same. Create something durable, restore clarity, and leave the organization materially stronger than it was before.

Who I Work With

I work with founders building something new, established companies navigating significant transformation, and PE or VC firms working alongside portfolio companies at critical moments of change. While the contexts differ, the underlying challenge is often the same. Something important needs to be created that does not yet exist. Whether inside a startup or a mature organization, my role is to help leaders recognize what is missing, build it deliberately, and transition it into the business once it is ready to scale.