When Should You Hire a Bookkeeper?

Kimberly Green | 2025-05-01

There’s a point in every business where DIY bookkeeping goes from scrappy to sloppy. Maybe it’s the third month in a row you’ve put off categorizing expenses. Or you’re not totally sure your income numbers are real. Or you find yourself preparing for tax season by saying, “Please God, let me not owe five figures.” This is the moment you’re asking: “Is it time to hire a bookkeeper?” Here’s how to know—and what to do next. 5 Clear Signs It’s Time to Hire a Bookkeeper “If you’re spending more than 30% of your time doing bookkeeping, it’s a sign you need help. Your business needs you doing business owner things , not reconciling Stripe payouts.” — Kimi, Co-founder of Sam’s List You don’t have to wait until you’re in the red to bring someone in. These are your red flags: You should hire a bookkeeper when: You're making $250K+ in revenue You're falling behind on tax prep or 1099s You have contractors, payroll, or inventory You want monthly financial reports (and don’t have time to do them) You’re not totally sure how much money you’re making—or spending For eCommerce, real estate, and startup founders especially, these systems get complex fast. Hiring a bookkeeper helps you catch cash leaks, prep for taxes, and actually understand your business. How Much Does It Cost? Bookkeepers can charge hourly, monthly, or offer fixed packages. Here’s a quick breakdown: Type Cost Range Freelance bookkeeper $20-$50/hour Monthly contractor (remote) $300-$900/month Boutique firm $700-$5,000/month Need someone vetted who actually responds ? Find a bookkeeper on Sam’s List . When to Hire a Bookkeeper Your Situation DIY Bookkeeping Hire a Bookkeeper Just getting started, under $100K revenue YES Not Yet $100K-$250K revenue, <30 transactions/month Maybe Helpful $250K+ revenue or hiring contractors Risky Strongly recommend Managing inventory (e.g. eCommerce, real estate) Complicated Hire Behind on taxes or unclear on financials Dangerous Hire Spending >30% of your time doing bookkeeping Inefficient Hire If you're not sure whether your books are accurate—or even up to date—that's your sign. Clean books = better decisions, smoother tax season, and faster growth. DIY → Pro: How to Make the Switch Here’s what to prep before you hand things off: Access to your bank, credit card, and payment processor accounts Chart of accounts (or let your bookkeeper create one) Income sources and expense categories Last...