What Makes a Great Bookkeeper Subcontractor (for Monthly Financials and Peace of Mind)
When you’re growing a business, messy books aren’t just a nuisance—they’re a liability. Whether you’re making $5K or $500K a month, solid bookkeeping helps you stay cash-conscious, make smarter decisions, and avoid chaos at tax time.
But if you’re not ready for a full-time hire (or an expensive CPA firm), a subcontractor bookkeeper is the perfect middle ground. The right one will keep your finances clean, organized, and up to date without ever becoming a bottleneck.
Here’s how to spot a great subcontractor bookkeeper—and what red flags to avoid along the way.
Why Hire a Subcontractor Bookkeeper?
A skilled bookkeeper helps you:
- Track income and expenses accurately each month
- Stay compliant with taxes, contractors, and reporting requirements
- Generate easy-to-read P&L statements and balance sheets
- Understand your cash flow and spending patterns
- Get clean books ready for tax prep, fundraising, or forecasting
It’s not just about keeping your books tidy—it’s about making confident, informed decisions.
What Makes a Great Bookkeeper Subcontractor?
1. They Understand Your Business Model
Strong bookkeepers don’t just know debits and credits—they know context. They’ll ask:
- How do you make money (subscriptions, services, products)?
- What tools do you use (Stripe, PayPal, Shopify, QuickBooks, etc.)?
- Do you have recurring expenses, contractors, or payroll?
- Are you cash- or accrual-based for tax purposes?
They tailor their process to your business—not the other way around.
2. They Set Up (or Clean Up) Your Chart of Accounts
A great subcontractor will make sure your Chart of Accounts is:
- Streamlined and relevant to your business
- Easy to understand (so you actually use your reports)
- Categorized to support tax deductions and financial analysis
- Structured to evolve as your business grows
If you’ve been lumping all expenses into “Miscellaneous,” they’ll fix that fast.
3. They Reconcile Transactions Monthly (Without Chasing You)
Bookkeeping only works if it’s done consistently. The best subcontractors:
- Reconcile bank, credit card, and payment processor accounts monthly
- Categorize every transaction and flag the unclear ones
- Send monthly reports (e.g., P&L, balance sheet, cash flow summary)
- Keep everything current—so you’re never behind at year-end
You’ll get regular reports you can actually read, not just a spreadsheet full of chaos.
4. They’re Proactive About Questions and Fixes
Strong bookkeepers don’t just do the books—they watch your books. They’ll:
- Flag suspicious or duplicate charges
- Ask about business/personal split expenses
- Remind you to send receipts or clarify vendor payments
- Help clean up errors before they become problems
They’re not passive—they’re looking out for you.
5. They Know the Tools You Already Use
Modern bookkeepers should be fluent in:
- QuickBooks Online or Xero (or both)
- Stripe, PayPal, Square, Shopify, etc.
- Gusto or Deel for payroll/contractor payments
- Hubdoc, Dext, or Dropbox for document collection
- Google Sheets or Notion for shared summaries
They can plug in seamlessly without making you reinvent your financial system.
6. They Keep You Ready for Tax Season (and Audits)
Come tax time, you shouldn’t be scrambling. A great bookkeeper helps you:
- Tag and track deductible expenses properly
- Cleanly separate business and personal costs
- Provide clean reports for your accountant or tax preparer
- Keep records organized in case of audits or due diligence
You’ll never dread “pulling together your books” again—because they’re already done.
🚨 How to Spot a Bad Bookkeeper (and Save Yourself a Headache)
Here’s what to watch out for when hiring a subcontractor bookkeeper:
❌ They’re Always Behind
If your books are still a mess in April and they say, “I just got busy,” that’s a red flag.
❌ They Only Communicate at Tax Time
If you only hear from them once a year, your finances are flying blind.
❌ They Don’t Ask Questions
A good bookkeeper should be curious and cautious. Silence usually means missed details.
❌ They Can’t Explain Reports in Plain English
If they drop a balance sheet on your desk and disappear, they’re not helping you run your business.
❌ They’re Not Familiar With Your Tools
If they’ve never worked with Stripe or insist on desktop QuickBooks in 2025—run.
Where to Find Great Subcontractor Bookkeepers
Top places to look:
- Bench or Pilot – Managed bookkeeping services with monthly reports
- Upwork – Search “QuickBooks/Xero bookkeeper” with verified reviews
- Belay – Curated U.S.-based virtual bookkeepers
- Facebook Groups – Look in freelancer, solopreneur, or e-commerce communities
- CPA Referrals – Ask your accountant for a trusted bookkeeping partner
- Referrals – Other founders are often your best source
What to Ask Before Hiring a Bookkeeper
- What types of businesses do you typically work with?
- Which tools and platforms are you most comfortable using?
- How do you handle categorizing unfamiliar transactions?
- What kind of reports do you send monthly?
- How do you communicate if something seems off in the books?
The best subcontractor bookkeepers aren’t just number crunchers—they’re financial stewards who keep your business clean, clear, and ready for anything.
