From BigCo to Startup: 20 Tips for Evaluating Early-Stage Companies & Making the Leap

Choosing your next role is one of the most important investments you can make — but, unfortunately, no one hands you a ready-made toolbox for navigating big career decisions. And evaluating opportunities in the startup world — without much publicly-available information and data to grasp onto — can be an even trickier black box.

Even in a compressed job hunt, taking a few minutes to flip your perspective and consider the following framing can be extremely helpful: As a startup employee, you’re essentially an investor — with a portfolio of one company. “Working in smaller startups is investing your time — which is the most invaluable thing you have. When considering an early-stage startup role, ask yourself: Would you invest your own money into this company and this founding team?” says Vishal Kapoor, VP of PM and PMM at Affirm. 

But particularly for candidates coming from larger, more established companies, evaluating the outlook of and potential fit with a startup is a daunting prospect. So we spent the past few weeks reaching out to tons of folks in the First Round community for their advice on this timely question: What should folks be on the lookout for when they’re evaluating a role and the prospects of an early-stage company?

What we got back in return was heaps of relevant advice from sharp founders, operators, investors and advisors across the startup ecosystem, with tips specifically geared toward folks coming from a BigCo background who are considering joining a startup for the first time.

What follows is a list of 20 targeted tactics for evaluating an opportunity at a startup — from assessing the company and its long-term trajectory, to how you might fit with the team and role, to questions to ask during the interview process, and advice for shifting your mindset.

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