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Do I Need to Hire a Bookkeeper for My Small Business?

Many small business owners start out managing their own bookkeeping, but as the business grows the financial workload can quickly become overwhelming. Knowing when to bring in a professional bookkeeper can help protect your financial accuracy, save time, and give you clearer insight into the health of your business.

When Managing the Books Yourself Stops Being the Best Option

Part 1 of this 2-part series is our blog post “The Importance of Bookkeeping“. In it, we discuss the role bookkeeping plays in a company’s financial health, the benefits of staying up to date, and what business owners should know about bookkeeping and bookkeepers.

In this post, we take the next step and answer a common question business owners ask: do I need to hire a bookkeeper?

Let’s get to it!

  • I need to hire a bookkeeper — should it be an employee or outsourced resource?
    • I’m a Solopreneur – Do I Need to Hire a Bookkeeper?
    • I’m a Small Business – Do I Need to Hire a Bookkeeper?
    • I’m a Larger Business – Do I Need to Hire a Bookkeeper?
  • Why Staying Up-to-Date on Bookkeeping Matters
  • Unexpected Issues Accurate Bookkeeping Can Reveal
  • Common Bookkeeping Mistakes Small Business Owners Make
  • Why Written Bookkeeping Policies and Procedures Matter
  • Does Hiring a Bookkeeper Help Your Business?
  • How Accurate Bookkeeping Supports Business Growth
  • What are important things to know about bookkeeping and bookkeepers?
  • How a Bookkeeper Can Help at Different Stages of Business
  • Is Outsourced Bookkeeping the Right Choice?
  • Protecting Your Business When Hiring an Outsourced Bookkeeper
  • Control Access to Sensitive Software, Files, and Documentation
  • Ready to Level Up Your Business?

I need to hire a bookkeeper — should it be an employee or outsourced resource?

It depends on a variety of factors that include (this is not an exhaustive list):

I’m a Solopreneur – Do I Need to Hire a Bookkeeper?

For a solopreneur, the decision depends on the owner’s familiarity with bookkeeping best practices and the number and complexity of financial entries.

An outsourced bookkeeper can reduce the administrative burden related to payroll and unemployment taxes. However, if the bookkeeper is a 1099 contractor, a well-written consultant agreement is required, along with a clear understanding of what qualifies as a 1099 relationship under government regulations.

I’m a Small Business – Do I Need to Hire a Bookkeeper?

For organizations larger than a solopreneur, but less than $100K in revenue, the number of daily, weekly or monthly entries, and the number and complexity of these entries that would warrant hiring an in-house or outsourced bookkeeper.

I’m a Larger Business – Do I Need to Hire a Bookkeeper?

When a company is growing or reaches a certain size the question isn’t “do I need to hire a bookkeeper”. It becomes a resource monetary question of “should I hire an employee or continue to use an outsourced bookkeeper. For a larger or growing business, an in-house resource may be more cost effective depending on work load unless an employee can be crossed trained to handle bookkeeping activities. The goal is to do a benefits analysis and see what is the best short-term and long-term decision for the company.

Why Staying Up-to-Date on Bookkeeping Matters

There are many benefits to staying up to date on bookkeeping, far more than we can cover here. The examples below highlight a few common surprises, both good and bad, that businesses often uncover during regular financial reviews.

Unexpected Issues Accurate Bookkeeping Can Reveal

Surprise: During a monthly financial review, a company may discover payments applied to the wrong invoice, missing invoices, or unpaid client balances.

These issues are usually easy to fix when caught early. Payments can be reallocated, invoices created and sent, and clients contacted. The benefit is accurate revenue reporting and better cash flow visibility.

Common Bookkeeping Mistakes Small Business Owners Make

Another common issue—especially for solopreneurs—is improper expense tracking. This often happens when business and personal accounts are co-mingled or when personal expenses are incorrectly marked as business expenses.

Not all expenses can legally be attributed to a business. Monthly reviews help catch and correct these issues before they become tax or audit problems. Clean books also reduce friction when applying for bank financing or outside capital.

Why Written Bookkeeping Policies and Procedures Matter

Hiring a bookkeeper alone is not enough. Companies should also create written policies and procedures so expectations are clear.

This ensures in-house staff understand what needs to be done and outsourced bookkeepers know exactly how bookkeeping activities should be handled.

Does Hiring a Bookkeeper Help Your Business?

Yes. An experienced bookkeeper can handle these activities and, most importantly, free up time for business owners to focus on revenue generation and client support.

However, you need to hire the right bookkeeper. They need to understand your industry and your business, have proven skills and expertise, are diligent about quality control and deadlines, and have enough “authority” to push company employees to provide the documentation they need for the bookkeeping activities.

How Accurate Bookkeeping Supports Business Growth

Accurate books support effective tax planning and play an important role in business growth. They can highlight when changes are needed in financial practices and help identify pain points such as consistent negative net income.

If you don’t know how to analyze this information, it’s time to meet with an accountant—or with us if you don’t have one—so we can help close the loop.

What are important things to know about bookkeeping and bookkeepers?

Bookkeeping can be learned, but it takes time and accuracy. What you don’t have time or money to do is get it wrong. Fixing mistakes is expensive and can lead to interest, penalties, or audits.

How a Bookkeeper Can Help at Different Stages of Business

If you are self funding your business (meaning the company’s revenues pay for everything) and you don’t anticipate growing or having cash flow issues, then good bookkeeping will ensure you stay on top of the company’s finances.

If you are thinking of growing your business, then a good bookkeeper and accountant (and perhaps an outsourced Controller/Comptroller or Chief Financial Officer) can help prepare the company and its finances so that it has everything already at fingertips when it’s time for bank financing or outside capital.

Is Outsourced Bookkeeping the Right Choice?

If bookkeeping isn’t in your sweet spot, outsourcing may be your best option. But it’s important to engage with the right bookkeeper. If not, your company may be heading towards an expensive fix.

Protecting Your Business When Hiring an Outsourced Bookkeeper

Due diligence is critical before signing a contract. Ask for references, conduct interviews, and treat the process like hiring an employee. Strong checks and balances, and written processes protect both the business and the owner.

Regardless if it’s an internal hire or external resource, if you don’t know the questions to ask, we can handle the interviewing, and provide feedback and recommendations.

Bookkeepers will have access to sensitive financial and personal information. Business owners must control system access, follow PII regulations, and avoid granting administrator rights or unrestricted banking access.

You should get a release to run a background check before hiring or engaging them. You want to ensure that their criminal history is clear. Note: there are several laws surrounding background checks so it’s essential that your offer letters or contracts include language about this to protect the company from potential lawsuits.

Control Access to Sensitive Software, Files, and Documentation

The small business owner or a senior executive in larger businesses should always maintain control over access and be very select in the access rights you give anyone in the company. Even if you have absolute confidence in the person, we still suggest not doing it. Theses rights should stay with the business owner, or a vetted employee who is at the controller/comptroller or higher. This is a check and balance to ensure it is clear and known regarding what money is going into and coming out of the accounts.

The bookkeeper will have access to your accounting system and sensitive/confidential information such as personally identifiable information or PII. There are regulations surrounding PII that the company is responsible for following. “I didn’t know” is a weak stance and is probably not defendable in the case of a breach and subsequent lawsuit or investigation.

If the bookkeeper says they need access to reconcile your bank accounts in your accounting system, then set up privileges to allow for the export of transactions. We believe the transactions should be entered during the month, so the end of month reconciliation should be very easy using a copy of the statement. Whatever is done, there should be a written process on how and when to do it.

The most important advice we can give is DO NOT give the bookkeeper administrator rights or anything besides basic access to your bank accounts (especially to transfer, withdrawal, or setup ACH/wires), payroll service passwords, or the ability change payroll or vendor direct deposit information.

Ready to Level Up Your Business?

Need Help Deciding Whether to Hire a Bookkeeper or Outsource your Bookkeeping? A lot of companies put off this decision as it’s usually not in their comfort zone. No need to worry. This is in our sweet spot… we’ll help you with the decision..

Why do we push hiring a bookkeeper so hard? It’s fairly simple.

Accurate and timely bookkeeping is critical to financial health and a key part of a business’ health. If you’re unsure whether you need a bookkeeper, need help finding one, or have questions after reading this 2-part series, reach out through our contact page to start the conversation.

If you’re ready to level up your business, reach out via the contact page and we can set up a call to talk. We have comprehensive services to create a solution that works for you and your company.

We’re also happy to answer questions about this post. Leave us a note in the comment section, or reach out on the contact page.

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Copyright © 2026 Tripod Coaching & Consulting - All Rights Reserved. | Privacy Policy
Who is Tripod Coaching & Consulting®? (cont'd)

What is the tripod?

The tripod is the company’s attorney, accountant, and banker. These three individuals work with the business owner(s) to lay an initial structural foundation. There is a 4th very important component that is the top piece connecting the 3 legs of the tripod — the insurance broker. Many companies wait to connect with an insurance broker; however, this creates potential risk exposure. It’s essential to get the correct insurance policies in place before the company begins providing products and services to their customers.

The company then builds their revenue and growth on this foundational tripod.

The challenge of business operations

The challenge is most business owners and executives find business operations tedious, and it takes a backseat to activities that directly generate revenue. They often don’t have a solid understanding of business operations because it includes a lot of specific and nuanced areas that they may not have been exposed to before starting their business. Then after the business opens, many business owners focus on what they know — the services and products they sell. And most are really good at selling because they know their industry and ideal customer.

The issue is that without a strong foundation, the business may not survive over the long haul or when faced with challenges that have legal and monetary ramifications. Why? Because a company cannot sustain itself only through revenue.

So, why don’t entrepreneurs invest time and money in their business operations? Partly because they may not realize how important it is for long-term business success.

Diana also believes this is due to industry and entrepreneurial programs not offering outside services and training in business operations topics, particularly to small businesses.

Do a search for consulting services and you’ll find a lot of listings for sales, marketing, opportunity identification, recruiting, etc. But you won’t find many for business operations coaching and consulting. The reasons are two-fold. First, the other industries are associated with increased revenue and are a lot more fun to teach and provide. Second, because many of those consultants don’t realize the importance of business operations so they don’t incorporate it into their own business model.

Our mission

Our mission is to help organizations with their planning for the “what if”™.

  • What if we grow?
  • What if we want/need to hire people?
  • What if we need to expand to other states?
  • What if we want to sell the business?
  • What if we are sued?
  • What if we…

We help you plan for the “what ifs” you may know about and identify ones that you thought wouldn’t affect your business.