Escalate the tone, not the frequency. One firm reminder, then a late-fee notice citing your agreed terms, then a final demand giving a hard deadline before collections or small-claims. Spacing them ~7 days apart works best.
Can I really charge a late fee?
Only if your contract or original invoice stated it. A common, defensible structure is 1.5% per month (~18%/yr) on the balance after a short grace period. Use the late-fee calculator below to get the exact number.