I've been at a FAANG for 4 years but lost my passion for this particular company. I got an offer from a series C startup with 300+ employees. I really believe in this startup but I want to make sure I'm not going to regret leaving FAANG if things go south. I'm still concerned about my family's financial security.
Said startup is offering about 15% salary increase and a few hundred stock options that vest over 4 years. I already get more than the offered salary when you factor in bonuses and the unvested stock units from FAANG.
The startup engineering is also less technical than FAANG so they've offered me a title one level up.
My problem is that I don't know how to factor in stock options in my calculations. It's unlikely that the stock price will beat FAANG if the startup goes public. Should I ask for more stock options? What happens to stock options when a company gets acquired?
Which brings me to the more important point, which is that the main thing you should evaluate is the company's likelihood of shrinking, shutting down, or being acquired for too little money. In my mind, there are several important things to consider:
1. Do you believe in the product?
2. Is the growth vision realistic?
3. If you were in the founders' shoes, would you have thought it was necessary or a good idea to raise as much money as they did?
4. Do you believe it's realistic that the company will be acquired for at least a healthy multiple of the total amount raised? If you know who the likely prospective acquirers are, are they shitty companies or do they have a history of fucking up companies they acquire?
5. Do you understand and agree with their expansion strategy (how and where they're spending the money they raised) in terms of speed, direction, head-count, etc.
6. Do you trust the founders as people and as business leaders?
7. How much has earlier employees' stock been diluted in subsequent rounds?
If I didn't have positive answers to all of these questions, I would think twice regardless of the stock options. If I did have all positive answers, I'd ask for more stock options because why the hell not. The worst thing they can say is no.
Edit:
If you are planning on asking for more stock, it's really important that you:
A) Be prepared to give a concise and meaningful explanation/answer for why you want or deserve more.
B) Have a (preferably specific) additional amount you want in mind and an explanation about why that amount.
C) Give some thought to how you're going to approach the conversation. You don't want it to go like this: Can I have more stock? No. Why not? Instead, consider asking how they went about deciding what amount to offer. It'll help you figure out whether it's worth asking for more and how far you can push it. The answer will also tell you if they're bullshitting, if the number is totally arbitrary and pulled out of thin air, or if they've actually given thought to it and have a good reason (like they've worked out the proportion of the employee option pool they can safely give each new expected hire at your level).