I’m interviewing at a Series B startup, and the hiring manager keeps emphasizing how they wear many hats. In my experience, that’s usually code for we have no processes and you’ll be doing the work of three people. The equity package is tempting, but I don’t want to jump from the frying pan of public into the fire of a disorganized tech firm. What are the specific red flag questions I should ask during the next interview to see if their finance department is a disaster?

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Try and convert some of the equity package to either salary or a sign on cash bonus. Speaking from experience, left public for a role (with good salary and sign on) but also significant equity options and then was laid off three months later. I was gonna stick around to see the equity but its not always your choice.

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Wearing many hats at a startup isn’t necessarily a bad thing. You have to make sure it matches what you want out of it, but I wouldn’t necessarily say it screams red flag. If you are looking for stability, a startup might not be the answer. As for questions, just ask about processes in place and day-to-day.

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