If you’re spending late nights wrestling with receipts and spreadsheets, you’re not alone. As small business owners, we wear many hats—but that doesn’t mean we should wear them all at once. One of the most common time traps entrepreneurs fall into is trying to manage the books themselves. And while the DIY route might feel like a cost-saving move at first, the truth is: it’s expensive in ways you don’t immediately see. According to a report in 2023, 70% of small businesses outsource at least one business function—bookkeeping is among the top three. Let’s talk about how to hire a bookkeeping assistant—strategically and confidently—so you can free up time and focus on growing your business.
The Real Cost of Doing It All Yourself
If you’re a business owner who’s currently handling your own bookkeeping, ask yourself: how much is your time really worth?
When you’re knee-deep in financial admin, you’re not strategizing, marketing, or selling—you’re simply maintaining. And poor financial management isn’t just inconvenient; it can slow down growth, trigger cash flow problems, or worse—leave you in trouble with taxes.
Warning signs you’re spending too much time on bookkeeping:
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You delay invoicing or reconciling your bank accounts.
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Tax season always comes with panic.
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You struggle to interpret your numbers for decision-making.
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Bookkeeping cuts into your weekends or family time.
A good rule of thumb is: if bookkeeping eats up more than 5–7 hours a week, it’s time to bring in help.
What Is a Bookkeeping Assistant—and Why You Might Need One?
A bookkeeping assistant is a remote or in-house support role focused on keeping your daily financial records accurate and up to date. They’re different from an accountant or full-charge bookkeeper—think of them as your first line of defense against financial chaos. So, what does a bookkeeping assistant do?
They manage tasks like entering transactions, managing accounts payable and receivable, preparing reports, and even assisting during tax season. More than a tactical hire, a bookkeeping assistant can become a strategic ally—giving you real-time clarity over your numbers and saving you from costly oversights.
This is especially valuable if you’re running a lean operation where time management is essential for entrepreneurs like you.
Key Tasks a Bookkeeping Assistant Can Handle for Your Business
Hiring a bookkeeping virtual assistant for your small business means offloading tasks like:
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Daily transaction entry (expenses, sales, bank feeds)
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Managing accounts payable (bills) and accounts receivable (customer payments)
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Creating and sending invoices—and chasing late ones
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Performing bank reconciliations
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Tracking expenses and flagging inconsistencies
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Preparing monthly and quarterly reports
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Supporting tax prep and financial compliance
Imagine not scrambling during tax season because everything’s already organized. Even if you outsource tax filing to an accountant, your VA can prep and package everything for them—saving time and money.
In-House vs Outsourced Bookkeeping: Which One’s Right for You?
Let’s weigh your options.
Hiring In-House:
✅ Pro: Real-time access, integrated into your team
❌ Con: Higher cost (salaries, benefits), limited flexibility
Outsourcing Bookkeeping:
✅ Pro: Lower cost, scalable hours, access to global talent
❌ Con: Less immediate control, requires clear communication
And yes, bookkeeping can absolutely be done remotely. The rise of cloud-based platforms like QuickBooks Online and Xero has made remote collaboration seamless. For startups and solopreneurs, a hybrid model (outsourced assistant + part-time oversight by a CPA) offers the best of both worlds.
Is it better to outsource bookkeeping? For most small businesses, yes—especially if flexibility, affordability, and access to skilled professionals are top priorities.
Where and How to Find the Right Bookkeeping Assistant
When you’re ready to hire a bookkeeping assistant, here’s where to look:
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Freelance platforms: Upwork, Fiverr, Freelancer. Ideal for project-based work.
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VA agencies: Check out directories or sites like Bold Assistants for pre-vetted professionals.
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Remote staffing firms: Many specialize in financial VAs.
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Local firms with remote services: Some accountants now offer part-time remote support.
Checklist for your job description:
✅ Clear list of tasks
✅ Required tools (QuickBooks, Excel, etc.)
✅ Time zone or availability needs
✅ Industry experience (if relevant)
✅ Trial project expectations
Always vet platforms for trust signals—read reviews, ask for client referrals, and verify credentials.
How to Evaluate Candidates Effectively
It’s not just about finding someone who can crunch numbers. You want someone who understands your business and can grow with it. The skills a bookkeeping assistant should have are:
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Experience with QuickBooks, Xero, or your preferred tools
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Comfort with Excel or Google Sheets
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Knowledge of basic financial terms and principles
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Strong attention to detail
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Communication skills for updates and clarifications
During Interviews with candidates when filling the position, some red flags to watch out for are:
- Vague about previous clients
- Inconsistent timelines
- Unwilling to do a small paid trial
- No understanding of your business model
Give a small task—like reconciling a sample statement or identifying missing transactions. It’s worth the effort to avoid a mismatch.
Ensuring Security, Accuracy, and Compliance in Outsourced Bookkeeping
Worried about sharing sensitive financial data? That’s valid—and manageable. Here’s how to secure your setup:
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Use password managers (e.g., LastPass) to share login details securely
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Store data in Google Drive or Dropbox with restricted permissions
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Sign NDAs and ensure your assistant understands confidentiality expectations
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Confirm compliance with relevant financial laws (e.g., IRS, GDPR) based on where you and your assistant operate
PAA Integration: Is it safe to outsource bookkeeping? Yes—with the right tools and agreements in place, it’s safer than trying to juggle everything alone.
Understanding the Cost of Hiring a Bookkeeping Assistant
How much does a bookkeeping assistant cost? That depends on a few key factors:
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Location: U.S.-based VAs may charge $30–$60/hour. Offshore VAs (e.g., from the Philippines) can charge $8–$20/hour.
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Experience level: More experience = higher rate, but often higher accuracy.
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Scope of work: Basic transaction entry is cheaper than full reporting.
Many providers offer monthly packages, which range from $250 to $800/month depending on workload. Track your saved hours and reduced errors to calculate ROI—it’s often higher than you’d expect.
Setting Up Your Bookkeeping Assistant for Success
Hiring is just step one. Success depends on strong onboarding and systems. To achieve this, you should start by:
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Clear Standard Operating Procedures (SOPs)
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Tool access (e.g., QuickBooks Online, Slack, Asana, Google Drive)
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Shared calendar for recurring check-ins
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Sample reports for reference
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Weekly or bi-weekly syncs
Most guides skip over the setup phase. But this step sets the tone. Think of your onboarding as an investment in future accuracy.
Making the Most of Your Bookkeeping Assistant’s Role
Your bookkeeping assistant isn’t just there to track expenses. Use their insights to make strategic moves. You can ask them to:
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Create monthly reports with notes on trends
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Highlight overdue invoices and spending anomalies
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Support you during tax prep or funding rounds
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Build forecasting models with your input
And when they’ve proven consistent? Consider upgrading them to a full-charge bookkeeper role—with expanded responsibilities and compensation.
Free Yourself to Focus on Growth
When you hire a bookkeeping assistant, isn’t just about saving time—it’s about gaining clarity, control, and confidence in your finances. As your business scales, your systems must too.
We’ve seen countless entrepreneurs reclaim their time and energy by offloading bookkeeping to vetted assistants through platforms like Bold Assistants. And you can do the same.
You don’t have to dive into full outsourcing on day one. Start small. Scale smart. Let your assistant grow with your business—and you’ll wonder how you ever managed without them.
Ready to hire a bookkeeping assistant and lighten your load? Start exploring pre-vetted options at Bold Assistants or learn more about remote talent in our expert hiring blog.
FAQS
What is a bookkeeping assistant?
A bookkeeping assistant is a professional who supports financial record-keeping, data entry, and basic accounting tasks for a business.
What does a bookkeeping assistant do?
A bookkeeping assistant records financial transactions, reconciles accounts, manages invoices, and assists with financial reporting.
Is it better to outsource bookkeeping?
Outsourcing bookkeeping can be more cost-effective and efficient, especially for small businesses with limited in-house resources.
Can bookkeeping be done remotely?
Yes, bookkeeping can be done remotely using cloud-based accounting software and secure file-sharing systems.
How much does a bookkeeping assistant cost?
A bookkeeping assistant typically costs between $20 and $50 per hour, depending on experience and location.
What skills should a bookkeeping assistant have?
A bookkeeping assistant should have strong attention to detail, proficiency in accounting software, and a basic understanding of financial principles.
Is it safe to outsource bookkeeping?
Yes, it is safe to outsource bookkeeping if you choose reputable professionals and ensure proper data security measures are in place.
