How do you handle proposals and invoicing as a small business?

Curious how other small business owners manage the proposal-to-invoice workflow. I've been freelancing for a while and always struggled with this part. Writing proposals takes forever, then you have to track if the client even opened it, then manually create an invoice after they accept.

Some people use all-in-one tools, some use separate tools for proposals and invoicing, some just use Word + Excel and call it a day.

What's your setup? Especially interested in:

  • Do you use a dedicated tool or DIY it?
  • How long does a typical proposal take you?
  • Do you have a system for following up on sent proposals?
  • If you're in the EU: how are you handling the new e-invoicing requirements?

Posted Mar 2, 2026, 4:11 PM UTC

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