Look for someone who understands your industry and uses software you’re already working with or willing to adopt. A bookkeeper who has worked with businesses like yours will understand the specific transactions, deductions, and reporting needs that matter. Generic bookkeeping knowledge works for basic tasks, but industry familiarity means fewer questions and faster, more accurate work.

Check their communication style before you commit. Virtual bookkeeping only works if you can actually reach your bookkeeper when questions come up. Ask how they prefer to communicate, how quickly they respond, and how often you’ll get updates. Some bookkeepers are email-only with 48-hour response times. Others are accessible via phone, video call, or messaging apps. Make sure their style matches how you operate.

Security matters more with virtual bookkeeping because your financial data lives in the cloud and gets accessed remotely. Ask about their security practices. Do they use encrypted file sharing? How do they store your bank credentials? Do they have a secure client portal? A professional virtual bookkeeper should have clear answers to these questions without hesitation.

Get clarity on pricing and what’s included. Some quote a monthly fee that covers everything. Others charge hourly or add fees for services that should be standard. Ask specifically what’s included in your scope of work, what costs extra, and how they handle months with unusual transaction volume. Vague pricing usually leads to surprise invoices.

Ask for references and actually call them. A good virtual bookkeeper should have clients who can speak to their reliability, accuracy, and communication. If they can’t provide references or hesitate when asked, that’s a red flag. Online reviews help but direct conversations with current or former clients tell you more.

Look for someone who treats your business like a partnership rather than just another account. The best virtual bookkeepers want to understand your goals, not just process transactions. They’ll point out problems, suggest improvements, and grow with you as your business changes. Ongoing bookkeeping is a long-term relationship, so finding someone invested in your success matters more than finding the cheapest option.

Consider whether they can handle your state-specific requirements. Massachusetts has particular filing deadlines and compliance obligations. A Merrimack Valley bookkeeper familiar with local and state requirements will save you from missing deadlines or making errors that a bookkeeper in another state might not catch.

Finally, trust your gut. You’re giving someone access to your bank accounts and financial records. If something feels off during initial conversations, or if they’re evasive about their processes, keep looking. Starting with the wrong person costs more to fix later than taking extra time to find the right fit upfront.