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I think the right time to ask is the time you feel you can confidently share your contributions to the company and state your worth. I always felt like this conversation went over way better when I was prepared with accomplishments and salary comparisons and such.
Go into it with those contributions ready! I’m also at a smaller company and find being in contact consistently is key, but I have a manager who already does consistent 1:1s to discuss goals.
If there’s no formal review cycle, timing your ask around budgeting can help. For small companies, that’s usually Q4 planning or the start of the fiscal year. But honestly, if you’re making an impact and have clear wins, anytime can work, just tie it to results. Have you had a recent project or milestone you could anchor your ask to?
Enthusiast
When you can articulate why you’ve earned it with proof to back it up and also when the company for sure has the money. Don’t ask when they’re doing layoffs for example.