At what point does it make sense for a company to outsource bookkeeping?

I’ve been handling the books myself since starting my business. At first, it was prety manageable: a few invoices, basic expenses, one bank account, and not much to reconcile.

But as the company has grown, it’s become noticeably harder to stay on top of everything. We now have more transactions, multiple payment platforms, contractors, subscriptions, sales tax, and expenses that are not always obvious to categorize.

Nothing is completely out of control, but bookkeeping is starting to take several hours every week, and I’m increasingly worried about mistakes showing up at tax time. I also find myself postponing reconciliations because there’s always something more urgent to work on....

So I’m wondering: is there a typical company size or level of complexity where outsourcing bookkeeping starts to make sense?

Is it based on Monthly revenue? Number of transactions? Number of employees or contractors? Hours spent doing the books?

For those who outsourced it, what was the actual breaking point? And looking back, did you wait too long, or was outsourcing earlier not worth the cost?