Frequently Asked Questions
Answers about bookkeeping packages, pricing, onboarding, and support.
How do I choose between Essential, Growth, and Premium?
Essential is a strong fit for foundational monthly bookkeeping, Growth adds deeper reporting and review support, and Premium is best for businesses that want proactive weekly support and strategic guidance.
What does starting at pricing mean?
Starting rates apply to businesses with lower transaction volume and clean books. Final monthly pricing depends on complexity, transaction volume, and whether cleanup is needed.
Do you offer custom pricing?
Yes. Premium services are custom quoted based on reporting needs, support cadence, and strategic advisory requirements.
Are add-on services included in package pricing?
Add-on services such as cleanup, payroll coordination, sales tax support, and QuickBooks setup or training are quoted separately unless bundled.
Do you work with businesses outside Chicago?
Yes. Winslow Bookkeeping serves businesses across the Greater Chicagoland Area, including Naperville, Aurora, Wheaton, Downers Grove, Lisle, and Oak Brook.
Can you help clean up overdue bookkeeping?
Yes. Catch-up and cleanup bookkeeping are available for businesses that are behind and need accurate records before tax filing or planning.
What is your onboarding process?
We start with a consultation to understand your business, current systems, and goals. Then we set up or refine your process and begin a consistent monthly or weekly workflow.
How do I get started?
Request a consultation through the contact page to discuss scope, timeline, and package recommendations.
Still have questions? We can walk through your business needs directly.
Schedule a Consultation