At some point, most growing businesses hit a ceiling — not in sales, but in operations. One of the first places it shows up? Your books.
What started as a simple setup with a part-time bookkeeper or a friend-of-a-friend accountant is suddenly a source of stress. You’re moving faster, handling more complexity, and making bigger decisions. But the financial insight you need isn’t keeping up.
That doesn’t mean your bookkeeper is bad. It means you’ve outgrown the relationship. And knowing when and how to upgrade your finance support is one of the smartest decisions you can make for long-term growth.
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TL;DR
• Most businesses outgrow their bookkeeper before they realize it.
• Delayed reporting, missing cash flow visibility, and lack of financial accountability are major red flags.
• Enkel helps Canadian companies make the switch with confidence and scale with clarity.
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Signs You’ve Outgrown Your Bookkeeper
15 Must-Track Metrics & KPIs for Nonprofit Success
1. You’re Spending More Time Chasing Reports Than Reading Them
You shouldn’t have to double-check numbers or wait days to get financial visibility. If your reports are late, missing, or unclear (and you’re spending time cleaning them up), your back office isn’t serving you.
What better looks like:
Timely, accurate reports delivered monthly with notes on what’s changed and what to watch.
2. Your Bookkeeper Can’t Keep Up With Your Business
Maybe they were a great fit when you had five clients and one revenue stream. But now you’ve got multiple bank accounts, new software, and contractors across provinces — and the bookkeeping is falling behind.
What better looks like:
A bookkeeping team with the capacity and systems to scale alongside you, not slow you down.
3. They’re Not Tech-Savvy (and You’re Paying for It)
Still sending receipts by email or storing backups in Excel? If your bookkeeper isn’t using modern tools (like QuickBooks Online, Dext, or Wagepoint), you’re likely wasting time and missing out on better systems.
What better looks like:
A cloud-based bookkeeping setup that syncs with your business systems and removes friction.
4. You’re Getting Tax Surprises or Compliance Gaps
Did you miss a GST filing deadline? Forget a T4 summary? Get hit with an avoidable late fee? These aren’t just mistakes. They’re signs your bookkeeper may not be proactively managing your obligations.
What better looks like:
A partner who flags deadlines, helps you stay compliant, and works clean all year — not just at tax time.
5. You Don’t Have Anyone You Trust to Explain the Numbers
It’s not enough to have financial data. You need someone who can help make sense of it. If you’re asking your bookkeeper questions and getting jargon or silence in return, you’re not getting real support.
What better looks like:
A responsive team that answers questions, explains changes, and helps you feel in control.
6. There’s No One to Call
Your bookkeeper’s unresponsive, on vacation, or juggling too many clients. You need answers, but all you get is silence or delays.
When to Switch (and How to Do It Right)
Switching bookkeepers can feel like a hassle. But staying too long with the wrong partner is worse. If any of the above issues are slowing you down, here’s when to make the leap — and how to make it stick.
When to Switch:
- Before your next fiscal year starts. This gives your new provider time to set up clean systems.
- After your year-end close. Easier handover. Less data cleanup during onboarding.
- Any time reporting feels risky. If you’re making financial decisions without confidence, don’t wait.
How to Make the Switch Smooth:
- Document key systems and logins. Who’s doing what? Where are the files? Who has access?
- Export your chart of accounts and latest reports. Make sure your new provider has a clear starting point.
- Ask your old bookkeeper for a formal handoff. Even if the relationship is strained, a clear transition saves pain later.
- Choose a new partner who can scale with you. More on that next.
Self-Check: Have You Outgrown Your Bookkeeper?
| Symptom | Impact | Action |
| No cash flow visibility | Risky decisions | Ask for better reports or upgrade |
| Books delivered late | Missed insights, CRA risk | Identify process gaps |
| Accountant fixing bookkeeping | Paying twice for the same work | Explore switching providers |
| Still using spreadsheets | High error risk, no audit trail | Invest in proper forecasting tools |
| No financial accountability | Blurred ownership, bottlenecks | Introduce financial oversight |
What to Look for in Your Next Bookkeeping Partner
Hiring another solo bookkeeper might solve today’s issue, but not tomorrow’s. Here’s what to prioritize if your business is growing.
| Feature | Why It Matters |
| Fast Month-End Close | You need timely data to make decisions, not a 6-week delay. |
| Cloud-Based Tech Stack | Tools like QuickBooks Online, Dext, and Wagepoint improve accuracy and efficiency. |
| Clear Communication Channels | No more “just following up” emails. Look for structured support and response times. |
| Defined Workflows and Deliverables | What’s included? When do you get reports? Who’s responsible for what? |
| Scalable Support | You might not need forecasting or cash flow modeling today, but you will soon. Choose someone who can grow with you. |
At Enkel, we offer all of the above. And we do it with the structure of a team, not a solo freelancer.
When a Bookkeeper Isn’t Enough
For fast-growing businesses, even great bookkeeping might not be enough.
Once your financials get more complex, with multi-entity setups, grant or investor reporting, or department-level budgets, you may also need fractional controller support.
This doesn’t mean hiring a full-time finance lead. A fractional controller gives you:
- Accurate, timely reporting with oversight. So you can trust what the numbers say.
- Better systems and structure. Standardized processes. No more chasing down receipts or explanations.
- Support for internal teams. Your ops lead doesn’t have to play part-time CFO anymore.
If your business is scaling, your back office should too.
Hiring a fractional controller isn’t about adding layers of bureaucracy. It’s about getting someone in your corner who can connect the dots and help you grow with confidence.
How to Make the Switch (Without Chaos)
Worried about making a mess during the transition? You’re not alone. But with the right partner, the switch can be smoother than you think.
Here’s how to do it right:
- Audit your current setup. Where are the bottlenecks?
- Review your contract. Know what your current provider is (and isn’t) responsible for.
- Gather your tools. What software are you using? Who has access?
- Define your goals. What do you want from your finance team: clarity, speed, strategic support?
At Enkel, we’ve helped dozens of growing companies make this leap and come out stronger, cleaner, and more confident on the other side.
Don’t Wait Until Something Breaks
Most clients don’t come to Enkel in crisis. They come because something feels… off.
They want faster books. Clearer numbers. Better support. And they want it without hiring an in-house team or dealing with disconnected freelancers.
If your current bookkeeper is slowing you down, or if your business has simply outgrown what they offer, we’re here to help.
Let’s get your back office working like a growth engine, not a roadblock.
