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Dear Quota Team

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I’m wondering if you have any advice for me. I currently have what I consider to be a pretty good sales job. It’s about 30% account management, 70% sales. I have a solid base salary and good company benefits. I’ve been here for close to four years and (until recently) had no intention of leaving. 

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A friend of mine from college left his product management role at a big tech company to work on his own startup about a year ago. He has a partner who is a developer and they have a product that’s out of beta with a few paying customers. They have self-funded this venture and have raised close to $700k from friends and family. They are in advanced talks with angel investors to raise a million dollars in funding which should be closing within the next few weeks.

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My friend reached out to me and asked me to leave my job and to come lead sales at his startup. I would be the only sales rep to start but would get the opportunity to build out a sales team as we raise money and get more customers. This would involve a pretty massive pay cut for me, but I would get stock options (up to 3% of the company after 4 years of vesting), and would get to have control over the company’s sales.

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Like I said, I had no intention of leaving my employer until my friend reached out. I know there’s a risk, but the upside seems almost uncapped, especially if this company turns out to be a unicorn. I don’t have any kids although I do have a mortgage, but I have enough of a nest egg where I could survive on the proposed income for a year or two. Do you have any advice as to what I should do? I don’t want to miss out on a huge opportunity.  

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Conflicted in New York

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Dear Conflicted,

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If you want to take the job, take it for the right reasons. There’s no place you can have as much of an immediate impact as you can at a startup, so if you’re looking to learn as much as possible, and gain invaluable experience, then you should consider making the jump. Just be ready for a level of stress and chaos you’ve probably never experienced before. 

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But you should also go into it with your eyes open. The overwhelming majority of startups fail, very few IPO, and many of those that do end up selling leave their employees with very little (or nothing) after investor liquidation preferences and the like. In this way, stock options are like a scratch ticket — you could hit big, but it’s more likely you won’t.

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Our advice is to think about what’s important to you. If it’s income and comfort, then stay where you are. But if you’re looking to jump into the fast lane, take a risk, learn a ton, and possibly get your heart broken, then join the startup. Just be sure you’re ready for what’s likely to come. Good luck!