About

We are living inside systems we didn’t design, don’t understand, and can no longer afford to ignore. These systems govern our institutions, technologies, communities, and choices—shaping how life works long before we realize they’re doing it. And here’s the uncomfortable truth: most of them were built without the people inside them in mind.

When design gets reduced to aesthetics or interface, systems fail. Not spectacularly at first, but quietly: in the frictions people feel, in the confusion teams inherit, in the widening gap between what leaders intend and what their systems allow. That gap is where meaning erodes—and where most organizations lose their way.

My work begins in that gap.

I study how design, systems, and human sense-making interact to shape behavior, power, and experience. If you are a designer, founder, or leader who knows your system is misaligned—or producing outcomes you never intended—my work helps you see what your system is actually doing and how to change it.

I came to this through philosophy, semiotics, and sociotechnical theory—fields that teach you to pay attention to the invisible structures guiding our lives. I spent years inside the machinery of healthcare and life sciences, founding companies and helping organizations navigate systems far more complex than the frameworks used to describe them. And I learned something consistent: systems rarely fail at the point of execution; they fail at the point of meaning.

My intellectual project, Thinking Design, takes this seriously. It is not a method or a set of tools. It is a way of understanding how assumptions become architecture, how architecture becomes behavior, and how behavior becomes lived experience. Drawing on systems theory, semiotics, sociocultural theory, and the history and philosophy of computing—and grounded in decades spent inside institutions that don’t tolerate abstraction without consequences—Thinking Design is a lens for seeing what most design frameworks leave out.

Where traditional design asks what to build, Thinking Design asks what your system is already saying.

I write, teach, and work with teams who want to see the deeper logic of their systems, name the stories those systems are telling, and build with more clarity, responsibility, and care. The goal is straightforward: systems that make sense to the people inside them.

When I’m not working with leaders or students, I’m riding. Tour de Ken is my multi-year project training for the 2,700-mile Tour Divide along the spine of the Rockies. These long, quiet, stubborn miles—the only kind I seem built for—are a laboratory for systems in motion: how bodies adapt, how environments push back, how tools matter, and how choices compound when there is no one coming to rescue you. Ultra-distance riding is systems thinking with consequences.

At home I read far too many books, cook far too many noodle-based meals, build furniture, make generative music, and take more photos than anyone reasonably should. I have a soft spot for the old Sierra adventure games and for analog instruments that reward patience and curiosity. None of these are hobbies so much as alternate entry points into the same questions about pattern, form, and meaning.

We live in a Japanese-style farmhouse in Northern Virginia, where my partner, Cecili, our younger daughter, Emerson, and our four dogs—Joey, Tone, Blue, and Ollie—fill our days with curiosity and joy. Our elder daughter Piper, now at Dickinson College, keeps me honest about the stakes of the work I do, while Emerson’s endless curiosity and Cecili’s insight remind me that every system I build is ultimately about people.

Everything I’m involved in—from building companies to mentoring founders to writing Thinking Design to riding very long distances—is part of the same project: understanding how we shape the systems we inhabit and how we might design them with more humility, rigor, and hope.

Current Roles and Projects

Academic and Intellectual

• Author of Thinking Design (forthcoming)

• Entrepreneur in Residence, McDonough School of Business, Georgetown University

• Professor, Communication, Culture & Technology, Georgetown University

• Research Associate, Georgetown University (sociotechnical theory, semiotics, history and philosophy of computing)

Professional

• Founder and CEO, Watershed LLC

• Vice President of Operations, Wider Circle

• President, Ask Claire

• Senior Advisor and Editorial Lead, GenMAV

Community and Mentorship

• Mentor, Techstars

• Mentor, Georgetown Entrepreneurship

• At-Large Board Member, Temple Rodef Shalom

Creative and Endurance Projects

• Tour de Ken – documenting the multi-year journey to the Tour Divide

• Bikepacking, randonneuring, and ultra-endurance cycling

• Photographer, builder, generative musician

• Lovelace Games (currently in stealth mode)