Monthly Financial Close: How to Tell if You Have the Right Bookkeeper

The business examples in this post are composite profiles based on common patterns we've observed across hundreds of Canadian service-based businesses. While the names and specific details are fictional, the challenges, solutions, and outcomes reflect real situations faced by business owners.

Is Your Business Outgrowing Your Bookkeeper?

You've built a thriving design agency. Your team is growing, your clients love your work, and your revenue keeps climbing.

But here's a question worth asking: Is your financial support growing with you?

For many business owners like you, the bookkeeper who was perfect during startup might not be the right fit as you cross $200K, $1M, or beyond in revenue.

What is a "Monthly Close" (and Why Should You Care)?

Think of your monthly financial close like checking the dashboard of your design software. You need to know how many projects you've completed, if any client concerns are pending, and whether your creative direction is still aligned with your business goals.

Meet Alex, who runs a branding and digital design agency billing $1.8M annually. For years, she made decisions based on her bank balance and gut feeling.

“I had clients and projects lined up, but I couldn’t tell you if last month was actually profitable until weeks or months later—sometimes not until tax time,” Alex says. “It was like designing without a concept brief.”

The Real Cost of Flying Blind

When your monthly numbers are always late (they should be ready by the 15th of the following month, at the latest), you're:

• Quoting projects without knowing if similar past work was profitable

• Unsure if you can afford that new design software or hire

• Missing early signs that certain services (like social media management) are losing money

• Making decisions without the full picture

• Waking up at 3AM wondering if everything's really okay

The bigger your agency grows, the faster you need your financial information. Top design firms with $3M+ revenue don't wait until the 15th—they have their numbers within days.

What Your Monthly Financial Checkup Should Include

A good bookkeeper should deliver these basics every month:

• All accounts matched up - Your bank accounts and credit cards reconciled with your books

• Who owes you money - A clear list of outstanding client invoices

• What bills you need to pay - Upcoming expenses and when they're due

• Your monthly scoreboard - Income statement showing if you made a profit

• Tax deadline check - Reminders about upcoming GST/HST, payroll, or other requirements

• Red flags and wins - Any concerning patterns or notable successes

Signs You've Found the Right Bookkeeper

Your bookkeeper is likely right for your growing design business if they:

• Show up reliably - Your monthly numbers arrive by the 15th without you having to chase them down

• Use modern tools - They've set you up with user-friendly systems like QuickBooks Online, not just basic accounting software

• Keep you in the loop - You have access to your financial information whenever you need it

• Respond promptly - They acknowledge your messages within 1-2 business days, even if just to say "I'll look into this by Friday"

• Speak plainly - They explain things in clear language, not confusing accounting jargon

• Point out issues - They highlight potential problems before they become emergencies

• Stay in their lane - They focus on excellent bookkeeping and work well with your tax accountant

• Grow with you - They offer additional help as your business expands

Warning Signs Your Bookkeeper Isn't Keeping Pace

It might be time for a change if you notice:

• Always playing catch-up - Your monthly numbers are perpetually late

• The vanishing act - It's hard to get responses to your questions

• Paper chase - You're still dealing with shoeboxes of receipts or manual processes

• Groundhog Day - You repeatedly send the same information because they can't find what you already provided

• Locked out - You can't access your own financial information when you need it

• Manual payments - You're still manually paying bills and vendors yourself

• Defensive responses - Your questions are met with excuses rather than answers

• Tech resistance - They avoid newer tools like Dext or Plooto that could make your life easier

• Always overwhelmed - They constantly seem behind with no system to manage their workload

How Often Should You Hear From Your Bookkeeper?

At minimum, expect:

• Monthly updates - Completed financial reports by the 15th of the following month

• Regular responses - Replies to your questions within 1-2 business days

• Clear communication - Easy ways to share information and get answers

If they're handling more for you, also expect:

• Payroll updates - Confirmation when payroll is processed through Wagepoint

• Bill payment schedules - Regular updates on what bills are being paid via Plooto

• Issue alerts - Prompt notification of any problems needing your attention

Essential Software Your Bookkeeper Should Be Using

Your design business deserves modern financial tools, not outdated methods. A good bookkeeper should set you up with:

• QuickBooks Online (QBO) - Your financial hub that you can access anytime

• Dext or Hubdoc - For capturing receipts from client meetings or design purchases

• Wagepoint - For managing your creative team's payroll correctly

• Plooto - To streamline bill payments and client collections

• Communication tools - Slack or similar for quick questions without interrupting your creative flow

• Project management - ClickUp, Basecamp, or similar for tracking bookkeeping workflows

• Google Workspace - For secure document sharing and collaboration

If you're still dealing with paper receipts, manual data entry, and paying bills by writing checks, you're missing out on tools that could save you hours every week to focus on your design projects.

What Should Land On Your Desk Each Month

By the 15th of each month, you should receive simple, clear reports showing:

• How much money you made - Your monthly profit or loss

• Your financial position - Assets, liabilities, and equity

• Who owes you money - Outstanding client invoices

• What you owe others - Bills you need to pay

• Any red flags - Issues that need your attention

• Upcoming deadlines - Tax or other requirements to prepare for

These aren't just numbers on a page—they're the insights you need to make smart decisions about your next design projects, software investments, and hiring plans.

How You Can Help Your Bookkeeper Help You

Even the best bookkeeper needs your cooperation:

• Share receipts promptly - Send them via Dext as they happen, not in a monthly dump

• Explain unusual expenses - Note the purpose of any non-standard spending on design assets

• Respond to questions - Provide information they need to categorize transactions

• Discuss priorities - Let them know what financial information matters most to your design business

• Provide feedback - Tell them what reports are most helpful for your creative agency

Finding a Better Fit: What to Look For

If you've realized your current bookkeeping setup isn't working, here's how to find a better match:

• Consider your size - Look for someone experienced with design businesses your size

• Ask about timing - When will you receive your monthly reports?

• Talk about technology - What tools like QBO and Dext will they use to make your life easier?

• Check references - Talk to similar creative businesses they support

• Discuss communication - How and when will they be available via Slack or other channels?

Questions worth asking:

• "When will my monthly reports be ready?"

• "How do you handle digital receipts and online invoices?"

• "What happens if you're sick or on vacation?"

• "How quickly do you typically respond to questions?"

• "Can I see a sample of your monthly reports?"

• "How will you make my financial picture clearer?"

• "Which software systems do you use for design businesses like mine?"

Focus on Growing Your Business, Not Chasing Financial Data

The right bookkeeper ensures your foundational financial needs are covered, giving you:

• Peace of mind that you're compliant with corporate tax, GST/HST, and payroll tax requirements

• Confidence that government filings are submitted correctly and on time

• A solid financial baseline to answer your basic business questions

• Freedom from tax-time stress and last-minute scrambling

• A foundation for working with advisors on profit and cash flow strategies

• Clarity on when and how much you can pay yourself

Your successful design business needs reliable Level 1 financial support before you can benefit from higher-level strategic guidance. Without timely, accurate books, you're building your business on shaky ground.

Ready to explore what proper financial support looks like for your design business? We're here to help.

• 30-minute discovery call

• Review your current financial setup

• Discuss your specific design business needs

• Get clear recommendations

P.S. While this tax season might already be underway, getting your monthly close process sorted now will make next year's tax time smooth and stress-free. Start today, and you'll never face another tax season unprepared.

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*Based on patterns seen across hundreds of Canadian service-based businesses.