As someone who has worked at quite a few startups this is the wrong question to ask. Out right failure is pretty easy to detect, and it kind of doesn't matter.

As someone who has worked at quite a few startups this is the wrong question to ask. Out right failure is pretty easy to detect, and it kind of doesn't matter. A startup failing fast is the second best outcome (after a nice exit) for everyone involved, including the investors. Startups that fail slowly are the worst, because there is an illusion of success that can drag everyone along for years. Always keep in mind that the odds will always be astronomically high that you are working for a startup that will fail. You're probably working for a startup that's going to fail. Most startups fail fast (but never employ many people), but the startups that hire the most people fail slowly, so the odds are very high that you are working for a startup that will fail slowly. So what should your question be then? It should be: Am I enjoying my job and/or does this job contribute to meeting my career goals? If the answer is no for too many months in a row and you are relatively sure the answer won't change and that you have no power over making it change then it is time to move on, with one highly unlikely exception: Your startup is succeeding and your equity stake is enough that riding the wave of a bad job for a year or two will result in a good chunk of money for you. So what are the signs of a company that is succeeding? There really easy to spot actually, even though you've never seen them: 1. Everyone's hair is on fire. Micromanagement is not a thing at your company because everyone is desperate to meet the insane demand and growth that your product has. 2. The technical work is very enjoyable, because the growth is insane. When you achieve incredible growth it actually stops managers from making decisions that don't scale, because the technical team will have numbers on their side of the argument. Your company can no longer afford to hack things together, because it has to scale tomorrow. 3. Talented people are banging down the door to work for your company. 4. Founders aren't talking about exits in terms of goals, but in terms of certitude. They've already received offers and they now have strategies in place to get the kind of exit they want. 5. BS of all forms is not experienced, because no one has time for it, even the people who normally spew it. 6. Hockey stick growth in either user growth or profit growth is trivial for you to see in your position. The founders don't have to convince anyone that your company is doing well, it's just plainly evident. If you are not experiencing these signs and you hate your job than it's time to move on. Founders hate to hear this, but if they haven't gotten traction in the first year-and-a-half they probably will never get it. There are notable exceptions, but it's important to remember that you are not the exception (does your founding team seem exceptional to you?).