Most MSPs start with an in-house bookkeeper. Sometimes it’s a family member, a trusted office manager, or even the owner logging into QuickBooks after hours. 

But as your MSP evolves – think more clients, larger contracts, or personnel changes – the financial complexity starts to outpace basic bookkeeping. At a certain point, it’s not just about what the numbers are behind your business. It’s about what the numbers mean. 

Depending on your stage of growth, you may need a bookkeeper, an accountant, or an outsourced partner who can cover both. The important part is recognizing when your current setup no longer gives you the clarity you need to grow.

An MSP-focused accountant doesn’t just “do taxes.” They bring strategy, foresight, and financial clarity, all of which are crucial for stable growth, clean audits, and long-term planning. If you’re at the stage where your bookkeeping/accounting needs a change, here are five clear signs it’s time to bring a professional into the mix. 

1. You’re Finalizing Deals but are Unsure If They’re Profitable

You are tracking revenue and making sure you remain VAT compliant, but are you tracking margins by deliverable or by client?

MSPs often manage multiple complex contracts, meaning there are specific circumstances where what appears to be a financial win is actually a loss. Fixed-fee agreements are susceptible to high-support clients that quietly chew away at your margins. The reality is that the “big retainer” client might actually be your least profitable one. Savvy bookkeepers and accountants who have experience with MSPs can identify this and guide you accordingly.

And if the numbers look good, then any investigation may stop there. But accountants can go a step further to provide insight and strategy by scrutinizing your line items. 

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And even with a detailed profit and loss (P&L) statement in your accounting software, most MSP owners don’t know how to interpret what’s really driving or draining profit.

That’s exactly what our Master Your P&L Statement: A Step-by-Step Guide for MSPs webinar series with Visionary360 digs into. Watch the on-demand webinar now.

They’ve helped hundreds of MSPs restructure their chart of accounts, properly allocate COGS, and finally see which service lines are carrying your MSP. 

2. You’re Planning to Scale or Hire but Lack Forecasting

Have you hesitated making a hire or investing in new tools because you’re not sure if your cash flow can support it? Has your finance team been able to give you insight into what the best move is? 

Growth without forecasting is more than just risky. It can mean ballooning debt, slicing into razor-thin margins, or missing growth opportunities because you waited too long to act. A recent Datto report, “State of the MSP Industry 2025” found that 91% of MSPs say profitability is a priority over the next 12 months, and 63% of them rank it as a high or top priority. That tells you many MSPs are feeling margin pressure right now, and making big investments blindly pushes you further into risk.

Accountants and built out finance teams (including bookkeepers) build forward-looking models. They forecast revenue, costs, and cash flow, showing you exactly when scaling is sustainable and when it isn’t. This way, you can confidently add headcount or upgrade your tech stack with the assurance that the numbers support the decision instead of sinking it.

3. Your Taxes Are Too Complicated To Handle In-House‍

The first out-of-state client is usually an MSP owner's “aha” moment. Suddenly, taxes aren’t straightforward anymore. 

For MSPs, multi-state clients, SaaS resale, and vendor pass-through costs make tax liability anything but simple. Missed deductions or misapplied sales tax means you’re either leaving money on the table or exposing yourself to compliance risk. And if something isn’t filed correctly, you would be the one held liable. 

That’s a lot of spinning plates. Think of it like managing multiple firewalls across different client environments; if you miss one configuration, the whole system is vulnerable.

This is where an outsourced professional can manage compliance end-to-end, saving you from juggling between multiple roles: 

• Multi-state compliance: Knowing when you’ve triggered nexus and must collect/remit sales tax in another state (a rule that varies wildly from state to state).‍
• SaaS resale clarity: Determining whether your SaaS pass-through is tax-exempt, taxable as software, or classified differently altogether.
• Vendor pass-through costs: Properly accounting for items you bill clients for (like licenses or hardware) so they don’t distort revenue or inflate liability.
• Credit card surcharging rules vary by state: some ban it outright, others allow it but require strict disclosures. Get it wrong, and you risk fines, angry clients, or double-taxation.
• Credits and deductions: Identifying and applying Section 179 deductions for equipment, and other MSP-relevant tax breaks.
  
  

Utilizing an experienced accounting professional results in fewer sleepless nights worrying about that specific line item on the tax form and more money kept in your pocket.

4. You’re Planning the Next Chapter for Your Business

Maybe you’ve thought about selling your MSP in a few years. Maybe you’re eyeing a competitor and wondering if you could afford to buy them out. Either way, the numbers on your books will define how much leverage you actually have.

Bookkeepers keep transactions accurate and records compliant. That’s the foundation you need for growth. But when it comes to major moves – like exits, acquisitions, and succession planning – the level of scrutiny goes way beyond keeping books clean.

If your chart of accounts isn’t optimized, if your margins aren’t clearly defined, or if your financials don’t tell a confident story, future stakeholders will hesitate. And hesitation almost always lowers value.

This is where accountants step in. They prepare you for valuation by normalizing EBITDA, clarifying expenses, and packaging financials in a way that investors or lenders can trust. In short, they take good bookkeeping and turn it into a compelling business case for your next chapter.

Think of it this way: bookkeeping provides the words, accounting builds the plot.

Automation strengthens that plot further. With FlexPoint, invoices, payments, and contracts flow seamlessly from your PSA into QuickBooks—reducing inconsistencies, avoiding costly clean-up, and freeing your finance team to focus on strategy instead of chasing missing details.

Whether you're looking to sell, merge, or acquire, the right combination of bookkeeping, accounting, and automation gives you the confidence (and valuation) to take the next step.

5. You Don’t Have Confidence in Your Numbers

If you don’t trust your numbers, you don’t really trust your business.

When “Are we actually profitable?” keeps you up at night, that’s a red flag. Same if an audit feels like your worst nightmare. Or if you’re thinking about selling in the next few years, but don’t know where to start. 

Uncertainty causes stress and it actively slows your growth. Without clear reporting, every major decision becomes a gamble:

• Pricing: You might raise rates too little (leaving money on the table) or too much (driving away good clients).
• Profitability: Are you leaning too much into managed services when tech services are better suited for your growth?
• Headcount: Hiring feels like a leap of faith instead of a strategic investment backed by forecasts.
• Acquisitions: Messy numbers put you on defense, not in control.
  
  

This is where accountants bring clarity to your finances. With proper classification, reconciled AR/AP, and GAAP-aligned reporting, your financials become a foundation you (and others) can trust. 

Whether that means pairing a bookkeeper with an accountant, or outsourcing the entire financial function, the goal is the same: trustworthy numbers that give you confidence in your decisions.

The Bottom Line

Bookkeepers keep your MSP running day-to-day: bills get paid, invoices go out, and transactions are recorded. That foundation is critical and you can’t grow without it.

But as your business matures, the financial questions shift from “what happened last month?” to “what should we do next?” And that’s where an outsourced accounting professional or full team comes in. They can work alongside your bookkeeper, building on clean data to forecast, model, and advise, or they can manage the entire financial picture if you don’t yet have bookkeeping in place.

The point is, no matter where you are in your growth journey, accurate bookkeeping and forward-looking accounting aren’t optional. They’re the foundation for profitability, smart scaling, and peace of mind.

Here’s the bottom line:

• If you’re questioning what’s actually profitable, you need more than bookkeeping.
• If you’re hesitating on headcount because you don’t trust your cash flow, you need an accountant’s forecasting.
  
• If taxes are getting complicated enough to make you lose sleep, you need an accountant’s expertise.
• If growth, exit planning, or acquisitions are on the horizon—you need both bookkeeping and accounting working together.
  
  

At any stage, investing in the right financial help is the difference between making guesses and making confident business decisions.

The reality is that most MSP owners don’t realize they’ve outgrown basic (or often DIY) financial support until a bad deal, an ugly tax season, or a missed growth opportunity makes it painfully obvious. Don’t wait for that moment. Bringing in the right financial support early can mean the difference between running a business that constantly feels like it’s “catching up” and one that’s proactively steering toward profitability. 

The best advice? Treat financial clarity like you treat cybersecurity: as a proactive investment, not a reactive cost. The sooner you build that clarity, the sooner you stop second-guessing every decision—and start running your MSP like the business you know it can be. 

And if you don’t know where to start, check out our bookkeeping and accounting guide to find experts who already know how your business works. 

If any of this hit too close to home, it’s probably time to see what the right financial system could look like for your MSP. Watch our on-demand demo to see how FlexPoint automates the busywork and keeps your books clean.