If that kind of interaction makes you uncomfortable, I guess you probably should go find another job since you might not have a great relationship with your company.
I (personally) feel that there's an implicit understanding with my employer, wherein my above and beyond efforts will result in increased compensation. If I feel like I've been clearly outperforming my compensation level and that's not recognized, I'm more likely to search for a new job than to ask for a raise, because my current employer has already failed to meet their end of the bargain.
In a well-run shop, managers have a very good idea as to who is worth what, and how much the company stands to lose if they lose good people. Staying one step ahead of this curve is a fundamental part of their jobs as a managers.
Obviously, the rules are a bit different in an early-stage start-up where the founders are doing everything at once and hoping something connects. But once an operation has hit cruising altitude, you really shouldn't have to ask for a raise if you're actually worth what your asking.
Your expectations around compensation should be based on explicit not implicit understandings. Making assumptions about how your emploeyer is going to make decisions about your compensation is not only likely to lead to disappointment, it's a poor way to maximize your salary if that's what you're interested in.
Most startups will hire (or push for hiring) a "senior person" at the "maximum rate allowed by the board". This includes a mix of stock/yearly comp.
Depending on hiring circumstances you can potentially push this. If there is a need, the will find a way to make things work out.
Once hired, from the employees perspective, it becomes a game of maintaining expectations. Unfortunately for the employee, in the case of startups (especially early), the expectations are quite high and any extra effort is tied in to the initial offer/hiring agreement.
Early stage startups are a gamble. There are often unexpected twists and turns. If you agree to X and Y at time T, three months down the line, the expectations at time U may be much greater.
As a non founding employee, your initial contract starts when you join with the expectations around the company when you joined. Carrying those same expectations along the way if the company is not growing in the same manner as you expected is a detriment to yourself.
When you realize this, it is time to re-evaluate and decide what is right for your current situation.
Does if fit your initial agreement? Then maybe you continue. If it doesn't, you need to consider renegotiating or looking elsewhere...
And people say jumping from job to job looks bad. If it does, I sure as shit haven't seen that side of it.
Some companies are willing to keep up, because they don't want to replace employees, but for most, it's cheaper to hire someone underpaid for a year or so until they jump ship, then repeat.
Sometimes they are actually trying, if the problem is internal politics preventing paying staff properly, but more often they're hoping you'll either forget about it or leave instead.
a) They don't value the work I am doing.
b) I am not doing work that is valuable enough to be noticed.
Both options mean it is time to look elsewhere.
That sounds like the kind of job hunt that puts you into the exact same position of frustration.