When should a small business hire a bookkeeper vs. using software?

Use accounting software solo when your transactions are simple (under ~150/month), you're comfortable reconciling bank accounts, and your books are current. Hire a bookkeeper when: your books are 3+ months behind, you're spending more than 5 hours/month on bookkeeping, you're making financial decisions without confidence in your numbers, or you're approaching tax season with unreconciled accounts.