Given all that, you are not being taken advantage of, although I could argue the equity to salary ratio is off, so either a little more salary or more equity.

Given all that, you are not being taken advantage of, although I could argue the equity to salary ratio is off, so either a little more salary or more equity. However, with only a $1M raise there isn't a lot of room to give you more salary, and I've seen really small employee equity pools in startups in the past few years so there may not be much there either. If the company had raised $3-5m then yea it isn't rare to see a CTO type in the mid to higher 100's, but then that person usually will have quite a bit more experience than you do. This isn't a knock against you in any way, this is just the realities of startups and business. While it is always fine to ask for a little more when certain events happen, like fundings, I don't think there is much room here for you to get any change. Although you might be able to negotiate $5-10k. You could angle for a bonus at a big milestone in the next 6-9 months, where 5-10k could be negotiated as a one-time bonus if you do well. That's easier on the business because it isn't an on-going operational cost and it can be justified by you doing something that really benefitted the business. Mind you it has to be more than you already promised or why would anyone agree to it. If you want/need to be in the six figures (we all have reasons for what we need/do), find a job at a larger company/startup, no faulting you in that if you have a need/want.