What are some important things to consider when applying to startups? I've applied to a few and think I'd like the idea of working for one but I am nervous about the unknown.

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Startups are varied so it depends.
I find the very young start ups (Series A and B) to be very full of themselves and it’s difficult to interview there because they want super top talent but their hiring processes are so young they have no idea who they’re looking for. Everyone is hoping their 10k shares can balloon them to 8 figures post IPO so they have some delusion (which keeps them alive).

Series D+ usually have their stuff figured out and I find the interview process to be not too different than most companies or recently IPOed startups. At this stage, you’re very close to IPO anyway so it makes sense to have things figured out.

In general I’d say learn about how equity works. Things like strike price, 409A, etc. and read the terms of the equity offer.

Startups are very volatile and majority of them fail and disappear. I know someone who has worked at 4-5 startups and has made $0 in stocks from them.

I’m working at a post IPO startup right now and the most crucial factors I considered was the product, history of company, leadership. The first two can be researched but leadership can only be confirmed during the interviews.

I’ve turned down offers at a lot of startups because I found the leadership to be weak. One person I thought was too arrogant and relied too much on his previous mild success would make him successful yet again. Another person I felt had very weak skills in selling business.

In my eyes, if leadership is bad, the chances the product will actually IPO lowers. And even if leadership is good, there’s still a chance the product fails anyway. But at least with strong leadership, I would’ve picked up valuable insight and skills from them.

helpfullike

Make sure the leadership is legit, one bad step and you can lose your job if it’s really small. Be prepared to wear 100 hats … as in you’re doing everything because sTArT uP culture. Once saw a finance manager role that was essentially expected to be the whole finance team and included tax responsibilities. Yikes.

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Believe the Glassdoor reviews, esp some of the more negative ones (while still trying to take it with a grain of salt bc in the end your experience may be a little different).
Learn more about their benefits - exactly how much PTO (even if unlimited) is offered, what are the monthly healthcare premiums and what’s the coverage carrier (see if you would have to potentially switch docs), what are additional perks they provide (gym reimbursement or cell phone/internet reimbursement, I think internet is prob only offered if you’re working from home usually), do they offer a 401k match, what’s parental leave, do they offer any tuition reimbursement (usually limited), etc.
Depending on how “early” the company is, the earlier it is means the more hats you wear. And if it’s later stage and you’re still wearing a lot of hats sounds like usually they didn’t get their stuff together well.
For some folks you work decent hours, for others the workload can make it into a 12 hr job almost daily (or at least weekly). Important how close you would be to leadership (how many “steps” away from the C-suite are you?) and how often you’d interact with them if that’s your goal. I also look at a couple of people in the roles I like at the startup (as well as other roles) and see how quickly people have been promoted to see the general norm.

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