Is My Small Business Ready to Hire a Bookkeeper?

Having to consider hiring a bookkeeper for your small business is one of the “good problems.”

It suggests that your business is gaining forward momentum—whether your brand is growing, pivoting, or just starting, your instinct to hire extra help likely means exciting developments are on the way. 

But, in the age of sophisticated, accessible accounting software, you may be wondering, “Does my small business need a bookkeeper?” Most likely, the answer is yes.

If one of the scenarios below sounds familiar, it is probably time to begin your talent search and evaluate your bookkeeping options.

#1 – You Are Overwhelmed with Bookkeeping Tasks

Managing your business’s finances can be complex and daunting—especially if you are the only person on the payroll. 

When starting a small business by yourself or with a small team, you have countless elements to oversee, some of which continue even after business hours are over:

• Market research
• Product or service development and brainstorming
• Branding, advertising, and outreach
• Estimating or proposing potential contracts
• Choosing a business name and legal structure (e.g., LLC, S-Corp, C-Corp)
• Securing real estate for a brick and mortar location
• Regulatory objectives (e.g., applying for a license, incorporating, requesting an EIN)
• Financials and bookkeeping

With so much on your plate, bookkeeping duties may be an unnecessary weight on your shoulders. If your business is scaling quickly—and you are struggling to keep up with billing and accounts payable—call in reinforcements to stay current, reduce your workload, and establish a strong financial foundation. 

#2 – Your Incorporation Status, Company Name, or Ownership Will Change Soon

Even if your business is not growing, it may be changing—a bookkeeper can help you manage transitions throughout your brand’s timeline, especially in its infancy. 

You may be preparing for one of the following major changes:

• Updating your incorporation status – If your production scale, risks, or staffing increase, changing your business’ legal status may reduce your tax liability or streamline your financial structure.
• Changing your company name – Rebranding and renaming can be a long, tedious process. You will need to prepare and submit documents to entities such as:
  • Your state and local business registration organizations
  • Any third-party regulatory agencies that issue licenses or permits
  • The Internal Revenue Service
• Selling or purchasing your business – It may be the right time to sell your startup, retire after a successful career as a small business owner, or purchase additional shares to become the sole or majority stakeholder. 

If you predict any of the above changes in your business’s near future, you need a high-quality bookkeeper on staff to assist with documentation and address the financial ramifications of these developments. Bookkeepers are experts in administrative duties, and any of the above transitions will require an all-hands-on-deck approach to ensure smooth sailing. 

#3 You Are Building Your Employee Benefits Package

Whether you expect to hire new staff soon or your employee benefits packages need an overhaul, bookkeepers can research options, perform administrative duties, and liaise between business leadership and service providers. 

Expect to complete the following tasks while you build or improve your slate of employee benefits:

• Determining the minimum requirements for employee benefits, which could include:
• Disability insurance
• Leave benefits
• Unemployment insurance
• Exploring industry-standard benefits packages to remain a competitive employer
• Researching providers and policies for each benefit type
• Securing quotes from numerous providers for each service
• Completing agreements and providing documentation to chosen providers
• Creating and organizing benefits enrollment paperwork for new employees

All of these tasks comprise a full-time job—at least temporarily. Even if your business only needs interim financial assistance while forming a new benefits package, hiring a bookkeeper is in the best interest of company leadership, current employees, and potential new hires.

#4 – You Expect Your Business to be Profitable Soon

Becoming profitable is every entrepreneur’s goal, but navigating this path can be intimidating for first-time business owners and long-time leaders alike. 

Luckily, bookkeepers are here to help. With their financial experience and documentation expertise, bookkeeping staff can help business owners tackle new objectives once they reach the black, like:

• Creating short- and long-term savings benchmarks
• Planning for future investments in equipment, staffing, marketing, or real estate
• Drafting company acquisition and/or sale timelines
• Negotiating new interest rates with leaders, refinancing loans, or increasing credit limits
• Budgeting for increased staffing
• Setting up auto-draft banking and other streamlined administration efforts

While unprofitability has its fair share of drawbacks, running a profitable business arguably requires more effort, more robust planning, and more accounting expertise. However, transitioning from the red to the black is much simpler with the assistance and guidance of a bookkeeper. 

#5 You Are Ready to Hire Additional Staff

If you are currently your company’s only employee, growth is as stressful as it is exciting. Scaling necessitates hiring additional staff, and a bookkeeper should be one of your first personnel investments to ensure each addition to your team goes seamlessly. 

This is because:

• Hiring increases your accounting task load – When you hire your first employees, you officially need to institute payroll procedures like pay schedules, benefits enrollment, tax payments, and direct deposit options.
• You need to stay on budget – With each new hire, you must confirm that their salaries, benefits, and associated expenses (e.g., computer, office supplies, reimbursements) remain aligned with your available budget. A bookkeeper will monitor these expenses so that growth remains healthy.
• Training takes time – As you onboard support staff, they will need training—which will require a significant time investment on your part. Even if you easily manage your business’ bookkeeping duties now, it becomes increasingly difficult to perform multiple roles concurrently at scale. Finding yourself a trustworthy bookkeeper will reclaim significant bandwidth.

When your business is ready to grow, a bookkeeper provides vital support as you invest in additional staff or your other responsibilities become more demanding. Preemptively bringing a bookkeeper on board will prevent avoidable challenges and reactionary measures.