I have always enjoyed working inside large enterprise environments—the legal counsel, the demanding CEOs and executives wrestling with hard questions, the creative and technical people, and getting deep into the weeds of processes and systems I may not understand yet.
You get to collaborate with people and teams who care about what they do, learn how that organization really works, how the industry functions, and design something that may eventually become part of the daily experience of thousands or even millions of people.
That kind of responsibility is incredibly rewarding.
Enterprise work also forces you to look far beyond design itself. You start understanding why certain decisions exist, why one department sees the problem differently from another, where technology creates limitations, where legal or compliance creates boundaries, and where users are getting caught somewhere in the middle.
A lot of the strategy is in connecting those pieces.
Sometimes it takes weeks of conversations, workshops, research, reviews, and disagreements before something starts to come into focus. And when it finally does, the design is carrying much more than a visual idea. It is carrying people’s knowledge, needs, constraints, and ambitions at once.
Slowly, all of that complexity starts becoming something people can actually understand and use.
But scale is not the only place where that kind of complexity exists.
There is another type of project that stays with me for a completely different reason. It is when I find myself sitting across from a founder who has spent the last ten, twenty, or thirty years building a company.
The room may be smaller and there may be fewer people around the table, but sometimes just as much history, knowledge, complexity, and responsibility is sitting right there in front of you.
They know every detail of the business. They know the customers, the relationships, the numbers, the difficult years, the breakthroughs, and probably a hundred stories that have never made it onto the company website.
Founders are usually moving fast. There is another customer to take care of, another person to hire, another problem to solve, another opportunity appearing somewhere in front of them. The rhythm becomes work, work, work, and then more work.
A design project comes along and, for a moment, we ask them to step outside of that rhythm and become part of the creative team.
We need to understand the story. And I often sense how much they actually enjoy taking on that creative role.
Some of the most interesting conversations I have with founders start with what appears to be small talk.
- Why did you start this company?
- What did you believe could be done differently?
- What happened during those first few years?
- What are you proud of today?
- What should never change?
- What do you want this company to mean ten years from now?
Those are not really small-talk questions. They begin shaping the structure and strategy for what comes next.
And when you spend enough time asking them, you begin uncovering pieces of a company that may have never been formally articulated.
Someone may tell you about an early customer who changed the direction of the entire business.
You begin connecting decisions made twenty years apart and realize there is actually a very consistent idea running through all of them. Sometimes that is the first time the founder sees that pattern clearly too.
Questions that seem small on the front end can uncover something much bigger underneath—a belief, a decision, a pattern, or a story that has been shaping the company for years without ever being fully articulated.
That discovery changes what you design next.
In an enterprise environment, after many workshops, perspectives, constraints, and conversations, the work eventually starts developing a point of view. It begins simplifying a system even though the organization behind it may be anything but simple.
With a founder-led company, the complexity can be just as significant, only compressed into a much smaller room. Sometimes the institutional knowledge of an entire organization is sitting across the table from you.
The challenge becomes extracting it rather than organizing it. Design becomes the process of distilling years of instinct, experience, and ambition into something clear. The build becomes the system that gives that thinking structure, consistency, and a life beyond the founder.
In a large enterprise, you are often bringing clarity to complexity. In a founder-led company, you are bringing structure to something that has largely lived through intuition.
Different conditions, but very similar responsibility.
Both require curiosity.
Both require good listening.
Both require understanding what matters before deciding what something should look like.
Early in my career I set a fairly simple goal for myself: I wanted to help companies communicate better. I still think about our work that way.
Sometimes that company is small and just beginning to understand who it wants to become. Sometimes it is growing quickly and needs its identity and digital experience to catch up with the organization it has become. Sometimes it is an established enterprise trying to bring clarity to decades of products, services, systems, teams, and ideas.
And sometimes it is a legacy company arriving at the point where it needs a new chapter without losing everything that made it important in the first place.
The scale changes. The responsibility really does not.
And the work changes us too.
You cannot spend weeks untangling an enterprise system, or sit across from a founder uncovering something that has lived mostly in instinct for twenty years, without carrying some of what you find into the next project.
A conversation with a founder can change how I think about entrepreneurship. An enterprise project can reshape how I think about scale and systems. A nonprofit can remind me how much responsibility comes with making information understandable. A company going through a transition can teach me something about leadership, resilience, or timing.
Those experiences accumulate.
They become part of the way you approach the next assignment.
And then the next one.
That is probably why, after all these years, I still have difficulty judging a project by its size.
A smaller engagement can completely change the trajectory of a company.
A large digital platform can quietly improve an experience for millions of people.
A rebrand can help a founder finally articulate something they have carried in their head for twenty years.
The interesting question is rarely, “How big is the project?”
The better question is:
What will be different because we did it well?
For me, that has always been the part of design that matters most.