When Should You Hire a Bookkeeper?

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:

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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.

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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

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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.

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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 year’s tax return
• Any outstanding invoices or bills

Not sure where to start? Bookkeepers on Sam’s List can clean up your old books and get your systems in place fast.

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FAQ

When should you hire a bookkeeper?

Once you’re earning $250K+, falling behind on reconciliation or taxes, or spending too much time on admin tasks.

Do I need a full-time bookkeeper?

Not always. Most small businesses can hire someone monthly or part-time.

What happens if you wait too long to hire help?

Disorganized books can lead to cash flow surprises, tax penalties, and lost time fixing preventable mistakes.

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You Might Also Like:

1. How Much Does a Bookkeeper Cost?

2. Stop Doing Your Own Bookkeeping

3. DIY vs Outsourced Bookkeeping

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Author: Kimi, Co-founder of Sam's List

Kimi writes about what she's learning while building Sam's List and shares honest takeaways from her conversations with accountants and financial advisors across the country. None of this is financial advice—just the stuff most people wish someone told them sooner.