Thriving as a Designer at a Rapidly-Scaling Startup

Insights from the FirstMark Design Driven series, a monthly event that brings together design, UX and product leaders to share new ideas.

When Josh Long started working at Oscar Health two years ago the company had 50 employees, 10 customer service reps, operated out of a quarter of one office building floor, and had a $200 million valuation.

Today, the health insurance company has more than 500 employees, 150 customer service reps, occupy three full floors and have commanded a $1.75 billion valuation.

It’s the type of swift scaling that entrepreneurs dream of.

In their own words, Oscar is “using technology to make insurance simple, intuitive, and human.” A huge piece of what Oscar is building revolves around a smartly designed user experience.

That’s where Long comes in. As the company’s product design lead, he has been tasked with arranging pixels in a way that make securing health insurance a breeze.

Long recently spoke to 300-person crowd of entrepreneurs and designers at FirstMark’s Design Driven NYC and offered up four important lessons he has learned trying to scale a design team at a rapidly growing startup.

Don’t wait for things to happen
After Long started at Oscar he got the feeling that people didn’t really understand the role of a designer. It took a while for him to get everyone up to speed.

“It meant writing down ideas. It meant making presentations to people. Talking about process. Telling them what designers did,” Long said.

What’s more, he started cranking out designs and soliciting feedback.

“[It meant] really pushing, not waiting for anyone to give anything to you because it’s not going to happen, especially in an organization that doesn’t understand where things fit right now,” he said.

In short - start making stuff.

Everyone has the right to come up with ideas
Oscar has a varied employee group that ranges from doctors to customer service agents to sales to engineers. And, every team has an idea about how to make the product better.

Long believes it’s important to pay attention to those disparate voices, particularly as the company scales and the product evolves. The doctors are going to know how the company can better connect with doctors. Customer service agents may have ideas that can reduce call volume.

Designers and product managers get to sit in the middle with open ears, collecting the best ideas and making them real.

Experts need to be able to make big decisions
Long said that at the end of the day teams have to trust that when a design decision needs to be made, a designer can make that decision.

“I’m not going to make a decision about a medical thing over a doctor, it’s just not going to happen,” Long said.

Teams need to be collaborative and open to helpful new knowledge, but an individual's expertise needs to be respected.

Don’t be precious about anything
Long says this is his most important point. Often we can get so enthusiastic about our own ideas that we lose sight of the greater good. As mentioned in previous points, ideas from all over the company are encouraged, but not all of them will make it to production.

Don't hold on to ideas too tightly. You have to be willing to let go, move forward and work as a team to find the best solution. 

Still growing with learnings to lean on
Long remembers not so long ago being a two-person team and watching projects pile up.

“We were burning ourselves out,” Long said. “It was a crazy experience. I was doing everything on the visual side. If anything went out, I had designed it. That gave us a lot of consistency, but the design process was getting thinner. We were cutting corners on things.”

Today, the 5-person product design team is trying to avoid feeling that stress again. There will always be problems to solve, such is the case at fast-growing startups. But Long’s advice for being proactive and open to external ideas during the design process, while also having the confidence to position the design team as the authority on subject, will serve Oscar -- or design teams of any size -- well as the company continues to grow.