When It Makes Sense to Hire a Bookkeeper
The key indicators your books need professional support
Most business owners start out wearing many hats. It saves money, it feels manageable, and in the early days you often have more time than clients. This is normal. Very few entrepreneurs open their doors with a full staff. Most of the time, it is just you, and maybe one or two partners, doing everything you can to keep costs low and momentum high.
One of those hats is usually bookkeeping. In the beginning, tracking your own income and expenses feels simple enough. A handful of transactions each month. Low volume. Easy to keep up with.
But as your business grows, the number of transactions grows with it. At some point, doing it all yourself stops supporting your business and starts holding it back. Bookkeeping gets treated like admin work and pushed off until later. Then tax season arrives, and you are scrambling, filing extensions, and telling yourself you will get to it soon.
You are not alone. Many business owners feel embarrassed when their books are behind. They assume everyone else is perfectly organized. The truth is that almost every entrepreneur I speak with has fallen behind at some point. Finances are personal, but they are also the only tool that shows you how your business is truly performing.
Below are the clear signs it is time to outsource your bookkeeping, and how to know whether you need a virtual bookkeeper or someone in house.
Signs It Is Time to Outsource Your Bookkeeping
You Spend More Time Bookkeeping Than Running Your Business
Bookkeeping is not complicated, but it requires consistency. If you are spending more hours reconciling accounts than generating revenue, serving clients, or finding leads, it is time to outsource. Bookkeeping is not a revenue producing task, but it is a revenue driving tool. Your time should be spent on the work that grows your business.
You Are Chronically Behind on Your Books
Life happens. Seasons get busy. But if you are constantly months behind, you cannot make informed decisions. Looking at numbers from three months ago does not help when you have cash flow issues today.
A healthy business should receive financial reports within ten business days after a month closes. That is when you can see trends, monitor margins, and make adjustments before problems grow.
Monthly financials should never feel out of reach.
You Are Guessing Categories or Avoiding Your Accounting Software
This usually happens when you are behind. Trying to remember what a transaction from four months ago was for becomes nearly impossible. Business owners juggle hundreds of tasks. Memory is not a bookkeeping system.
When you outsource, your bookkeeper asks questions within days of each transaction, while the details are still fresh.
Tax Season Feels Stressful or Disorganized
If tax time requires hours of catch up, late nights, or extensions, that is a clear sign you need help. With a bookkeeper in place, tax season becomes as simple as sending your CPA a clean year of financials.
Your Business Is Growing and the Finances Feel More Complex
As revenue grows, so does complexity. Invoices, due dates, vendor payments, accounts receivable, accounts payable. You need a clear system that shows what is coming in, what is going out, and when cash flow changes are expected.
A bookkeeper keeps everything organized so nothing slips.
You Want Accurate Financials to Make Better Decisions
You started your business to solve a problem or fulfill a purpose. Not to become an accountant. A bookkeeper has experience across many industries and can guide you through situations you are facing for the first time.
Your Accountant Suggests You Bring Someone In
When your CPA tells you your books are messy or incomplete, it is time. They want clean numbers so they can file your taxes accurately. Bringing in a bookkeeper will simplify the process and reduce long term costs.
Why Outsourcing Bookkeeping Saves You Money
Outsourcing your bookkeeping is an investment in your profitability. Here is why:
You Uncover Missed Expenses and Deductions
If you are not reconciling regularly, you may miss expenses or forget to enter transactions. Missing deductions leads to overpaying taxes.
You Get the Data You Need to Raise Prices and Plan for Growth
Accurate reporting highlights trends in sales, seasonality, margins, and cash flow.
You Prevent Mistakes That Lead to Costly Cleanup Work
Submitting messy books to your CPA can result in additional clean up fees. Clean books reduce those risks.
You Get Time Back to Focus on Revenue Generating Work
Bookkeeping cannot be rushed. Delegating it gives you hours back each month.
When It Does Not Make Sense to Outsource Yet
Not everyone needs a bookkeeper from day one.
It might not be time yet if:
You are brand new and have very limited transactions
You do not have consistent revenue
You have fewer than fifty transactions per month
You enjoy doing it yourself and have the time to stay consistent
For businesses not ready to hire, the Ledger Tracker is the perfect tool. It supports up to three bank accounts, has built in check figures, and helps you stay organized without the cost of software.
What Outsourced Bookkeeping Looks Like
When you hire a bookkeeper, you should expect:
Error free monthly financial reports
Clear communication
Someone watching your numbers all year
Accurate records
A partner who helps you understand your numbers
As a QuickBooks Online ProAdvisor, Oak and Ledger clients also receive their QuickBooks subscription at no cost.
What Happens During Your First Month With a Bookkeeper
Your onboarding should include:
Connecting all bank and credit card accounts
Setting up or optimizing your QuickBooks file
Reviewing your business model
Understanding how your systems integrate
Cleanup or catch up work if you are behind
Bringing everything current to the most recent month
Reviewing your first full set of financials together
This creates a clean foundation so you can move forward with clarity.
Virtual Bookkeeper vs In House Bookkeeper
For most small businesses (under one million in annual revenue), a full time in house bookkeeper is not necessary.
A remote bookkeeping firm makes more sense when:
You need clean monthly financials
You do not have full time bookkeeping needs
You want a consistent flat monthly rate
You want reduced overhead compared to hiring an employee
An in house bookkeeper makes sense when:
You need someone available instantly throughout the workday
You want someone to handle administrative tasks
You need in person support for daily operations
And while you’re here, if you are looking for payroll support, check out ADP for your payroll solutions.
Final Thoughts
Your business is growing, and your support system should grow with it. Your time is your most valuable asset. Partnering with a bookkeeper ensures your finances stay steady while your roots grow deeper.
When you are ready to take the next step, schedule a consultation. If you are not ready for a bookkeeper or software, the Ledger Tracker is a great first step to keeping your numbers organized.
ADP Payroll
A streamlined payroll solution with dedicated support for small business owners.