Don't ask. Tell. Do some research about what your comp should be, and then tell them. "Hey, boss. I've been here for two years. I've built this MVP, upgraded t

Don't ask. Tell. Do some research about what your comp should be, and then tell them. "Hey, boss. I've been here for two years. I've built this MVP, upgraded this system, and make most of the tech decisions. I've increased revenue by $A and decreased latency by B%. I've mentored this person and that person. Given that it's been two years, and the value that I have brought to the company and market rate for the role that I am performing, a C% raise bringing me to $XX,XXXX seems to be a reasonable comp adjustment. Let me know what you think." You have leverage here (other offers/opportunities). You aren't begging for more money -- you're stating the facts. You are saying "I'm worth this much. If you agree, then we're good." And if he doesn't agree... well, you have options, right? Happy to help more if I can, but this is my best advice as a manager. Good luck!