Read this before joining as employee 1 to 20 at a startup

It’s week six in your new job at a bootstrapped startup, and the founder asks you: “Create a prototype of our software to share with investors. We don’t have a company name yet. And I need it in two days.” If this sounds familiar, chances are you’ve been an early employee at a startup. If this is your precise scenario, you’re Stacy La, Clover Health’s Director of Design.

When La first started with Clover Health, it was just the founders, head of product and a data scientist. She was its first designer and the company hadn’t raised any money. Now she leads an eight-person design team, Clover is 500+ people-strong and the startup has raised over $425M. Though La was a seasoned design leader (Yammer, Microsoft) before Clover Health, it was her first time as a very early employee forged in the crucible of a fast-scaling company.

In this exclusive interview, La reduces nearly every motion of an early employee to flexing one of two muscles: ruthless prioritization and high-return troubleshooting. For the former, she outlines a sequence of time management milestones to expect as an early employee in year one. For the latter, La asserts that every challenge must produce double the return in takeaways — and gives examples of that principle in action.

Ruthless Prioritization as a Timeline

From the list-making apps like Asana and Things 3 to hyperfast email like Superhuman, there are many tools that can help generate greater efficiency. Then there are philosophies from productivity aces like Getting Things Done’s David Allen or Lifehacker’s Gina Trapani. All these resources can be valuable for the overworked, under-resourced early employee, but according to La, time management operates as a unique frequency for a startup’s first employees.

“At the start, it was fun taking the leap and deciding to get involved as an early employee. I was back together with people I had worked well with before,” says La. “But then it got daunting very quickly. The magnitude of the task ahead hit at once: my hybrid doer/leader role for a functional area, my learning curve in the health insurance space, and all the opportunities that Clover could go after in the market. Suddenly, spinning up felt more dizzying than galvanizing.”