When to hire a bookkeeper, according to experts

One of the best parts of running a small business is the pride of getting everything off the ground yourself. Not everyone has the vision and drive required to successfully take a concept and bring it to life. And the thought of hiring external staff, like a bookkeeper, can feel a bit daunting.

“Early on, when you’re just starting out, it’s manageable to track everything yourself or use basic software. But as your business grows, you might find that managing all those invoices, payments, and expenses becomes overwhelming,” explains Steven Kibbel, certified financial planner and founder of Kibbel Financial. “I’ve seen small business owners who wait too long to address this and end up with errors in their books, missing payments to vendors, or even misreporting revenue.”

Sure, you might pride yourself on running a lean business, but a good bookkeeper should be seen as an investment, one that helps you track and retain more of your hard-earned money and frees up your time to focus on what you’re best at.

If you’ve been wondering whether or not you need outside help to track and manage your small business expenses and income, you’ll want to read on. Here are the tell-tale signs that it might be time to hire a bookkeeper, according to a certified financial planner and a small business tax advisor.

1. When you’re unable to keep track of the inflow and outflow of cash

“As your business grows, managing your own books can quickly become overwhelming. You might lose track of who owes you money, miss vendor invoice deadlines, and struggle to accurately track cash flow,” says Alex Cook, VP of Small Business Tax at Block Advisor. “Reliable cash flow management is crucial for making informed business decisions that ensure long-term success. However, if bookkeeping isn't your strength, it can hinder your progress.” 

According to Cook, untangling financial messes on your own can consume valuable time that could be better spent on sales and revenue generation. If this sounds familiar, it might be time to outsource your accounting to a trusted provider.

2. When bookkeeping starts eating into your time

Another big trigger is when bookkeeping starts eating into the time you should be spending on running and growing your business. “I worked with a client who owned a small retail shop, and she told me she was staying up until midnight every night trying to reconcile her accounts. That’s time she could have spent sourcing new inventory or marketing her business,” explains Kibbel. “Hiring a bookkeeper freed her up to focus on the creative side of her business, knowing her finances were in good hands.”

3. When you go international

Financial complexity is another issue. Think about it like this: If you start hiring employees or expanding into new markets, you’ll start dealing with payroll taxes, inventory tracking, or even multi-state sales tax compliance, which you might not be entirely proficient in. This is where a bookkeeper becomes invaluable because they can handle those details while keeping your records clean and accurate. “One of my clients who runs a small e-commerce business hit this point when she started selling internationally. The tax and currency issues got complicated fast, and she realized it wasn’t something she could keep doing on her own,” says Kibbel.

4. When tax season becomes a headache

“Tax season is a huge pain point for a lot of small business owners,” says Kibbel. “If you find yourself scrambling to pull together receipts and records, or worse, missing out on deductions because your books aren’t organized, it’s probably time to hire someone.”

“I’ve seen business owners save thousands in taxes because a bookkeeper ensures everything is categorized properly and ready for the CPA to review,” adds Kibbel. “And if you’ve ever been hit with a penalty for missing a tax deadline, you know how costly that can be.”