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.


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