What founding and selling a company taught me about leading design

Before Digs, I thought my job was to make great products. After Digs, I think my job is to help a company win, and design is the way I do it.

It sounds like a small change in wording, but it changed how I lead.

What Digs was

I co-founded Digs to help first-time buyers save for a home. We started with something small, an education product that explained the process of buying a house to people who found it intimidating. It grew into an FDIC-insured savings product that more than 20,000 people used to save for a down payment.

Then we built Digs Pro, a version that lenders and agents could offer to their own clients, and signed partners including Rocket Mortgage. In 2020 the company was acquired.

I led design the whole way through. I also did a lot of things that weren’t design, because when you’re a founder, the job is whatever the company needs that week.

You find out what the design was for

As a designer inside a bigger company, it’s easy to judge your work by how good it looks and how well it tests. As a founder, the measure is blunter. Did people sign up? Did they come back? Did a partner agree to put their name next to it?

That was uncomfortable at first and then it was freeing. I stopped polishing things nobody had asked for. I started asking, before any piece of work, what it was supposed to change for the business.

Digs Pro is the best example. It came from a founder’s problem: we had a consumer product people valued and no affordable way to reach more of them. Lenders already had the relationships. So the design question became what a lender would be proud to hand to a client. I was in the partner conversations as well as the design files, and the product was shaped by both.

Everything is design when it’s your company

The pitch is design, and so are the pricing, the onboarding email, the partner contract, and the way you explain the product in one sentence. Each one is a decision about how someone experiences what you’ve made.

I came out of Digs with much less patience for the idea that design is a department. It’s a way of making decisions, and the best designers I’ve worked with apply it far outside the interface.

Selling the company

Going through an acquisition is like a design review of the entire business. Someone outside looks at everything you built and decides what it’s worth.

What I noticed is which things held their value. The product mattered, of course. But so did the partnerships, the trust we’d built with the people using it, and the clarity of the story. The things that were hard to copy were worth the most, and very few of them were screens.

It also taught me to think about what lasts. A feature is easy to replace. A relationship with a customer, a way of working, a team that knows how to ship together: those are the durable things, and they’re what I try to build now.

What I took into leadership

A few things stuck.

• I hire for ownership. I want designers who care whether the thing works once it ships. The best ones act like it’s their company.
• I tie the work to a result. Every project should have an answer to “how will we know?” before we start. Movoto Homeowner bringing in more than a million new monthly users is the kind of outcome I want a team to be able to point to.
• I explain the business to designers. Most designers are never shown the numbers. When you show them, their work gets sharper, because they can see what matters.
• I’m calm about hard trade-offs. Once you’ve had to make payroll, a disagreement about a roadmap doesn’t feel like a crisis.
• I respect the people around me more. I’ve done a little of sales, partnerships, engineering, and support, all of it badly, and I know how hard they are.

Would I do it again

Yes. Nothing else has taught me as much as quickly.

I don’t think every design leader needs to start a company. But I do think every design leader should, at least once, be fully responsible for whether something succeeds. It changes what you pay attention to, and I think it made me someone a team can trust with more than the pixels.