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The Lakewood Scoop

When to Hire a Bookkeeper, When to Hire a Controller — And When You Need Both | Joe Herskowitz, EA

May 11, 2026·4 min read

One of the most common questions I hear from growing business owners is some version of this: “Do I need a bookkeeper, or do I need a controller? What is the difference, and how do I know what I actually need right now?”

It is a great question, and the honest answer is that it depends on the size and complexity of your business. But let me give you a clear framework so you can make that call with confidence.

What a Bookkeeper Does

A bookkeeper handles the day-to-day recording of financial transactions. This includes categorizing income and expenses, reconciling bank and credit card accounts, managing accounts payable and receivable, processing payroll, and keeping your books current so your financial statements are accurate.

Think of a bookkeeper as the person who keeps the financial engine running cleanly on a daily and weekly basis. They ensure the data is there and correct. What they typically do not do is interpret that data strategically, build financial models, or advise you on how to improve your margins or manage your growth.

A bookkeeper is the right fit when your business is relatively straightforward, your transaction volume is manageable, and you primarily need someone to keep accurate records and handle basic financial administration.

What a Controller Does

A controller operates at a higher level. They oversee the entire accounting function, ensure the integrity of your financial reporting, establish internal controls, manage the month-end close process, produce management reports, and often serve as a liaison between the accounting team and company leadership.

A controller is not just recording what happened — they are analyzing it, spotting trends, flagging risks, and helping you understand what your numbers mean for your business. They also bring structure: documented processes, a proper chart of accounts, consistent reporting, and oversight of whoever is doing the day-to-day bookkeeping.

You likely need controller-level support when your business is growing, when you are making decisions that require reliable financial data, when you are preparing for a loan or investment, or when your accounting has grown complex enough that a bookkeeper alone cannot manage it effectively.

The Case for Both

In many businesses, the ideal setup is a bookkeeper handling the daily transactional work, with a controller overseeing the function, reviewing the output, producing higher-level reports, and ensuring everything is accurate and strategically useful.

For many small and mid-sized businesses, hiring both of these roles full-time is not practical or cost-effective. That is where fractional and outsourced solutions become genuinely valuable. A fractional controller brings senior-level financial expertise at a fraction of the cost of a full-time hire, and pairs naturally with a dedicated bookkeeper to give you a complete, well-functioning accounting operation.

A Simple Rule of Thumb

If your primary need is clean, accurate, current books — start with a bookkeeper.

If you need someone to interpret your numbers, establish reporting, and bring strategic financial oversight to your business — you need a controller.

If you need both — and many businesses do — a fractional model gives you the coverage without the full-time overhead.

The worst outcome is hiring neither and hoping your spreadsheets and memory will carry you through. At some point, that approach becomes genuinely expensive. The errors compound. The blind spots grow. And the decisions made without good information start to show up in your results.

Invest in the financial infrastructure that matches your stage of growth. Your future self will thank you.

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About the Author:

Joe Herskowitz, EA, is the President and CEO of Lionstone Bookkeeping+, where he helps small and medium-sized businesses take control of their finances with expert bookkeeping and financial insights. With years of experience in business finance, Joe is passionate about making numbers work for business owners—not against them.

Have a bookkeeping or business finance question?

Reach out to Joe at [email protected] or call/text 732-803-7793 (no WhatsApp).

 

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