Depends on the industry, but during the interview it’s reasonable to ask about how well funded they are, product deadlines and when they will need to do crucial fundraising. I would ask if there is a deliverable coming up that could make or break the company (within an 18 month window, they should have detailed plans projecting that far), and whether you would be able to have an impact on the success of that venture. Also weigh the potential value of stock and equity compensation if the company is successful, as that upside, if combined with a competitive salary, can make the risk more palatable.
Ive launched a startup that grew to a pretty big company, it’s not so much the volume of work that’s a killer, it’s the lack of clearly processes and procedures that adds stress. It’s harder to objectively assess performance in that environment so often the whole staff really rises and falls on company performance strictly, making the dead weight people harder to carry. Usually the leadership is spread thin so there’s a lot of big picture delegating and novel problem solving, which I like, but that can sink people who are accustomed to working on very clearly defined assignments.
Additionally, they’ll often need to take on business to grow, meaning the work can increase rapidly despite slow growth in headcount.
Of course, these things combine under a worst case scenario to meaning a ton of work and high risk of failure, but it’s not constant, and that can be more interesting than filling a clearly defined corporate role.
Having done it, I don’t think I’ll go back to another job in a big, established company.
