I'm in a very similar situation in terms of discussing a short term consulting + possible CTO role. I don't know if we will proceed with it, but based on my pla

I'm in a very similar situation in terms of discussing a short term consulting + possible CTO role. I don't know if we will proceed with it, but based on my plan my advice is: First do the consulting gig, charge a proper market rate (cash, no equity) for the work and do a great job of it. Define an visible and achievable target for this, rather than starting to implement an open-ended project that you won't finish in the time. At the end of this, if everything goes well and you like the company, negotiate terms for the full-time role. This will be the right time to do it: You will be in a strong position having demonstrated your skills up close and produced something of value to the company. You've charged a good rate for your work so if you don't agree terms you also aren't "down" financially. During your consulting period, apply for other jobs (if that's what you want instead of your current consulting work). If you have some other good offers on the table, you will be able to walk away if their terms aren't good enough and you will have a good floor for your market value.