The Solo Designer: Lessons from a Startup Journey

Although I've only been a full-time designer at Summer Health for less than a year, I've been their sole designer for nearly three years. The company has evolved during this time. Since some of my most popular posts have focused on my day-to-day work, like "Working as a UX designer" and "Working as a UX lead", I thought it would be interesting to share my reflections on being a startup designer. I'll describe my typical days and the valuable skills I rely on, complementing Paul Stamatiou's post "The Startup Designer", which excellently outlines the general skills needed for this role.

In fact, I’ll start by sharing a quote from his post, because I think it beautifully captures what life is like:

There's nothing glamorous about being a designer at a startup. It's a role that frequently values speed and pragmatism over going deep in the craft. It's not all big launches, viral tweets, building for happy paths, and clear-cut product requirements.

However, it can be incredibly rewarding. The fun comes from being able to excel at learning new skills and wearing many different hats while being solely responsible for large efforts.

Though my title is "Head of Design," I'm essentially a design team of one for now, aside from a few freelancers we regularly collaborate with. This means handling everything from high-level macro design to nitty-gritty micro design.

Supporting different streams

Our team is still small (we're less than 20 people), and to some extent, I'm the one to support all aspects of the company with design. While my title is "Head of Design," it's spread widely as I'm also the one to execute on all of it. We do bring in talented freelancers to help out with design, so it's not as lonely as I'm making it sound. My work is mainly divided between three streams:

• Product- Most of my time is obviously (and thankfully) spent working on concepts, thinking, framing, researching, and designing features for our products. While it might seem like we only have one product, the touchpoint for parents, we actually have one more which is our EHR, CareOS, where our providers write medical notes, view patient history, and chat with our members. Since joining full-time, I've been fortunate to not only design more, but more thoroughly understand what to design, meaning I spend a good part of my days talking to parents, something I've really come to enjoy.
• Marketing - As we’re scaling the team and getting more and more members, it’s only natural to do more marketing efforts. I oversee design for everything from flyers, banners, one-pager pdf’s, company swag, as well as social media marketing design.
• Sales - From designing the deck that raised our Series A to sales collateral, I’m working with the business team to make sure we communicate as visually simple and elegant as possible.

“Once you get to Figma, most of the hard work is already done”

One of the highlights since joining full-time is getting to talk with our members—parents with kids—much more frequently. As an introvert, I find these sessions exhausting, but they provide invaluable knowledge. Looking back, it's astonishing how many websites and products I designed without ever talking to actual users! These conversations not only help me think about our product and design more holistically but also remind me why we do what we do as a company. Being the only remote employee (everyone else is in SF or NY), these reminders give me a powerful sense of purpose.

The sliding scale of giving a fuck

One of my recurring mantras for approaching work and advocating for features is "if everything is important, then nothing is." This phrase, attributed to Patrick Lencioni, author and leadership consultant, comes from his book The Five Dysfunctions of a Team. The concept highlights a crucial truth about prioritization: when everything is treated as equally critical, effective focus becomes impossible. Paul touches this in his blog post too;

The startup designer knows where to compromise on quality, when to push for it hard, and how to advocate for it beyond intuition, armed with customer feedback, insights, and company goals.

My favorite approach to this, which is less conventional and more startup-friendly, is Cap Watkins's "Sliding scale of giving a fuck"—a blog post I frequently reference. The core idea aligns: as designers, engineers, and makers, we naturally want to craft excellent products according to our vision. But true excellence emerges from teamwork, and as mentioned, when everything is important, nothing is. During feature discussions with team members, I often find myself rating priorities as a 5 or 7 on this scale—important but not critical. This approach means that when I do rate something as a 9, my conviction carries more weight.

I hope this look into my daily work helps you understand what it's like to be the first designer at a startup. Being the only designer isn't easy - you have to handle many tasks at once and make big design choices by yourself. But it's also really rewarding and gives you lots of chances to grow and make a real difference. You need to be flexible, resourceful, and okay with uncertainty, but it feels great to directly shape how a product grows. Even though there are long days and you have to switch between different types of work often, it's amazing to help build something from scratch. It's like being on a roller coaster that challenges your abilities and helps you become better at your job.