When joining a startup company that is anywhere from 5 to 50 people, what are some things I can/should ask for in a contract negotiation?
Can I ask for acceleration of my options if the company gets acquired before my cliff? Can I ask for a guaranteed contract with a buyout, in case they want to let me go before my options vest?
You can ask for these things, and I think a company's ability to have an informed conversation with you about your options will tell you a lot about the founders (both in terms of their expertise and their character).
Keep in mind, though, that founders have a lot more discretion with respect to how much they pay you than with respect to your options contracts. Garbage options contracts (no triggers, no guaranteed contract, huge cliff, etc.) are generally insisted on by VCs, in order to prevent employees (read: you) from negotiating an agreement which makes the company a less appealing acquisition target. Pay is generally more flexible.
So I'd suggest asking those questions, having an informed conversation with the company about the way options are structured, and then insisting on a good, solid salary and treating the options as gravy. By the time you get diluted, you end up in a locked up IPO gone south, or the acquirer comes up with some creative stock-and-cash acquisition with employee pool conversion that scams you, there's a very low chance of your options being worth anything anyway.
Can I ask for acceleration of my options if the company gets acquired before my cliff? Can I ask for a guaranteed contract with a buyout, in case they want to let me go before my options vest?