Let’s paint a picture: you’re running a growing business — 10, 20, 30 plus employees and counting. Maybe you’re onboarding a new team member every few months. Sales are up. Your services are expanding. Things are moving in the right direction.

But in the background, your IT setup is a bit shaky. You’ve got one person on staff who’s “pretty good with computers,” so they’ve unofficially become the IT person. They set up email accounts, tinker with printers, and occasionally call in help when something breaks that’s out of their depth.
It’s been okay for the time being.

Suddenly, your team is losing hours to weird system issues. You’re getting flagged for security vulnerabilities during a compliance audit you didn’t see coming. Files are scattered across machines, some still running Windows 10 (maybe?), and no one knows who’s in charge of what. You’re starting to worry that your business has grown beyond your technology’s ability to support it.

Now you’re asking yourself:
“Do we need to outsource IT?”
“Should I hire a full-time IT person?”
“Can we even afford either of those options right now?”

First off, you’re not alone. Most small to midsize businesses (SMBs) say that managing IT internally is increasingly overwhelming as they scale. The reality is that nowadays IT is foundational to how your business runs, secures data, serves clients, and grows.

This post will walk you through everything you need to know to make the right call. It’ll help you figure out:

• Whether you’ve outgrown your current setup
• What outsourced IT actually looks like
• How it compares to hiring in-house
• How to choose the right solution for your business goals

In the early days, a makeshift approach to IT can get the job done. Maybe you started with a few laptops, a shared Google Drive, and someone on the team who could figure it out when the Wi-Fi went down. But as your business grows, that ad hoc setup starts to crack under pressure. You’re now spending more time putting out fires than focusing on strategic growth.

Here are the clearest signs you may have outgrown your current approach:

If your unofficial IT lead is also your head of operations, admin assistant, or the company bookkeeper, this is a red flag. Multitasking mission-critical IT responsibilities with someone’s actual job role can create major blind spots and even burnout. Plus, they most likely don’t have the expertise needed to keep everything up and running and organized the way it should be.

Slow computers. Spotty internet. Inconsistent access to shared files. These little delays add up and cost real money. Small businesses lose an estimated $427 per minute of downtime. As your company grows, this number grows with it with medium-sized businesses losing around $9000 per minute of downtime.

If your new hires are spending their first few days hunting down login credentials, or worse, your offboarded employees still have access to sensitive systems, it’s another red flag. Strong IT infrastructure creates smooth, secure transitions and onboarding/offboarding that protect your company and save time.

With the growing rate of everything security from phishing emails to compliance audits, cybersecurity isn’t optional anymore. If you’ve started worrying about how secure your data really is, or you’re facing pressure from vendors, insurers, or regulators to prove your security posture, that’s a sign it’s time to level up.

As a business leader, your time is far too valuable to spend Googling how to configure a firewall or schedule backups. When technology starts eating into your focus, it’s no longer a behind-the-scenes tool and has now become a roadblock.

Most small businesses don’t wake up one day and say: “Today’s the day we invest in our IT!”

They wait… and wait… and wait.

And that’s not because they’re careless. It’s because running a business is a juggling act, and IT tends to be one of those things that can just be pushed to the backburner until it becomes a huge problem.

So why do companies hold off? Here are the usual suspects:

This one’s incredibly common: “We’ll look into that once we hit 50 employees” or “when we open our next location.” But IT problems don’t care how big you are, they get bigger as you grow, often faster than you realize. Growth should be the trigger of when you really start to invest in your technology.

Cost is the biggest mental hurdle. Many business owners assume that hiring IT support (especially an outsourced team) is a luxury reserved for enterprise companies with bottomless budgets.
In reality, outsourced IT services are often more affordable than hiring in-house, and they come with better tools, faster response times, and broader expertise.

Sure. You’ve patched printers. You’ve rebooted routers. You’ve Googled your way through one ransomware scare and lived to tell the tale. But running your business like a game of “whack-a-mole” takes a toll on productivity, security, and peace of mind.

The hidden cost of not taking action is what can kill. Delays, downtime, lost data, security breaches, regulatory fines, and employee frustration. These costs add up quickly and quietly.

Small businesses account for 43% of hacks in North America with the average data breach costing $6.32 Million for Canadian Businesses. But, even a much smaller-scale breach can devastate an SMB.

If you’re asking this question at all ~ “Do we need more IT help?” ~ the answer is usually yes. That internal doubt tends to show up after the friction has started. And the earlier you act, the smoother (and cheaper) the transition will be.

Outsourcing your IT isn’t about handing the keys to a stranger and hoping for the best. It’s about gaining a team of experts whose sole job is to keep your business running securely, smoothly, and efficiently while you focus on actually running the business.

If you’ve never worked with an outsourced IT provider before, here’s exactly what you can expect from the first conversation to day-to-day support and long-term planning.

Every good managed IT provider starts by taking inventory of your current setup. This includes:

• What devices your team uses (and how secure they are)
• How your employees access files and systems (locally, in the cloud, or… not sure?)
• How backups are handled (if at all)
• What software and platforms are in use (and who has access to what)
• Whether you have any compliance requirements (industry-specific or client-driven)

This not only helps gather data about your inventory and systems but also helps to identify risk. You might learn you’ve got admin accounts still active from people who left a year ago, or discover that your file sharing is wide open to anyone with a link.

This audit becomes the roadmap: it shows what needs fixing, what’s working, and where you’re exposed.

Another major misconception is that outsourcing means losing oversight. In reality, a good IT partner standardizes and documents everything, so you can stop relying on Steve’s memory of how the Wi-Fi was configured back in 2019.

With outsourced IT, your systems, processes, and permissions are actually written down, organized, and managed, not floating in someone’s inbox or brain.

Here’s an example:

Instead of everyone in the company using whatever email service they want, your IT provider sets up Microsoft 365 or Google Workspace accounts, standardizes permissions, applies security policies (like MFA), and ensures your branding and legal disclaimers are consistent across all communications.

A lot of people think outsourced IT is just being able to call someone when your Outlook crashes but that’s only maybe 10% of it. The real value is in proactive, ongoing support. Here’s what that typically includes:

• Help Desk Access: Your team can call, email, or chat with real techs when something breaks. No more dragging your “IT-capable” coworker off their real job.
• Remote Monitoring & Maintenance: Your systems are constantly monitored for issues from failing hard drives to outdated software and suspicious activity then, they are updated automatically.
• Patch Management: No more ignoring update pop-ups. Your provider ensures all operating systems and apps are kept current and secure.
• Onboarding & Offboarding: New employee? Your provider sets them up with a device, email, access to shared tools, and security training. Someone leaving? Their access is revoked instantly and securely.

One of the biggest upgrades when you switch from a DIY setup to a managed provider is baked-in security. It’s no longer “we hope the antivirus is doing its job”, it’s a full security program that runs in the background, protecting your data, your team, and your reputation.
This usually includes:

• Firewall and network protection
• Endpoint Detection & Response (EDR) to catch threats in real time
• Phishing simulation and employee security training
• Encrypted backups and business continuity plans
• Security policies and access controls based on roles
• Compliance support (e.g. PIPEDA, HIPAA, SOC 2, etc.)

Outsourced IT should be interconnected with your business processes. You get access to someone who understands how your technology impacts your business operations, customer experience, and future plans.
This role is often referred to as a Virtual Chief Information Officer (vCIO), and they’ll help you:

• Plan for upcoming hardware replacements or software upgrades
• Evaluate new tools or platforms before you invest
• Forecast IT needs as your team scales
• Set IT budgets that align with your business goals
• Build a roadmap to meet industry compliance standards
• This guidance helps you make intentional technology decisions so you’re not stuck rebuilding your systems every 18 months

Outsourced IT brings in expertise so you can stop putting duct tape on your technology and start building systems that support your business as it grows.

Now let’s talk about whether you should just hire someone full-time or bring on an external IT provider . A dedicated internal IT person sounds like a natural next step when your team starts hitting 20, 30, even 50 people. But hiring in-house isn’t always the slam-dunk it seems, especially for growing small businesses.

This is a full-time employee (or maybe even a part-time tech specialist) who becomes your go-to for all things IT. That includes:

• Help desk support for your team
• Managing hardware and software
• Handling security tools
• Maintaining systems and networks
• Vendor coordination (internet, software, etc.)

• Immediate on-site availability (if you’re in-office)
• Familiarity with your team, tools, and business model
• One consistent point of contact for all tech issues

• Cost: Expect to pay between $70,000–$100,000+ CAD for a qualified IT generalist in today’s market. And that’s before benefits, payroll taxes, PTO, and training.
• Limited expertise: One person can’t know everything — cybersecurity, networking, compliance, support, cloud migration… it’s a tall order.
• Burnout risk: If you’re growing fast or have unpredictable tech needs, your internal hire could quickly get overwhelmed.
• Coverage gaps: Vacations, sick days, or sudden turnover? You’re stuck without support when you might need it most.

This gives you a dedicated team of specialists, often for a flat monthly rate. The service scales with your business and usually includes:

• 24/7 remote support
• Proactive maintenance and monitoring
• Cybersecurity tools and training
• Strategic IT planning
• System upgrades and vendor management
• Help with compliance and audits

• Breadth of expertise: You get access to a full team, including cybersecurity pros, cloud engineers, and IT strategists.
• Cost-effective: Outsourcing can cost as little as $2,000–$4,000/month for a small-to-midsize business — far less than a full-time salary.
• Scalability: As your business grows, your IT support can grow with it. No need to recruit, hire, or train more staff.
• Availability: Coverage doesn’t disappear when someone’s on vacation — your provider is always online and staffed.

• May not be physically on-site (unless you arrange in-person support)
• You’ll need to communicate clearly to get the most value — especially early on
• Requires trust in a third party (though a good provider earns that quickly)

Here’s a good rule of thumb:

• If your business is under 100 employees, and you don’t have specialized security or infrastructure needs, outsourcing is almost always more cost-effective and reliable.
• If you’re in a heavily regulated industry (finance, healthcare, legal) and already have a mature and well-built internal structure, hiring in-house may make sense as a supplement often in partnership with outsourced support.

But for most growing businesses, especially those in the 15–75 employee range, outsourced IT gives you the flexibility, coverage, and expertise you just can’t get with one internal hire.

Okay, so you’ve decided that outsourcing your IT might be the right move. Now comes the part where Google hits you with a sea of options all claiming to be “reliable,” “proactive,” and “business-friendly.”

Unfortunately, not all IT providers are created equal.

Some are true strategic partners. Others are glorified help desks who vanish once the onboarding is done.

Here’s what really matters when evaluating an IT provider, especially if you’re a growing small business with limited time and a limited budget:

You don’t want to submit a support ticket and wait two days to hear back. And you definitely don’t want to explain the same issue to three different people every time something breaks.

Look for a provider that offers:

• Clear SLAs (Service Level Agreements) outlining response and resolution times
• A real person you can call or email (not just a chatbot or overseas help desk).
• Client-specific familiarity: They should know your systems, your people, and your environment

You could ask: What’s your typical response time for critical issues? Will we have a dedicated point of contact?

Cybersecurity is a foundational requirement. If a provider doesn’t lead with security, run.
A solid partner will include:

• Endpoint protection and patching
• Email filtering and phishing protection
• Multi-factor authentication (MFA) enforcement
• Secure backup and recovery systems
• Cybersecurity awareness training for your team
• Compliance support if needed (e.g. PIPEDA, SOC 2, etc.)

Bonus: they’ll talk about security in a way that makes sense, not like they’re just reading from a firewall instruction manual.

The best IT partners do everything to help you prevent problems. They think ahead and guide you as your business grows.
This is where that “vCIO” role (virtual Chief Information Officer) comes into play. They’ll help you:

• Plan upgrades and avoid last-minute scrambles
• Evaluate new tools and platforms based on your goals
• Budget for future IT needs before they sneak up on you
• Keep your systems aligned with your industry’s best practices

You shouldn’t need a decoder to understand what’s included in your service plan. A trustworthy provider makes it crystal clear what you get and what you don’t.

Plenty of providers know how to configure a router. Fewer understand how IT impacts real-world business outcomes.
You want a partner who asks questions like:

• “What does success look like for your team?”
• “Where are the bottlenecks or pain points right now?”
• “What are your goals for the next year, and how can technology support them?”

If the only question they ask is “What firewall are you using?”, they’re not thinking big enough.

You’re choosing a long-term partner who will directly impact how your business runs, scales, and stays secure.

When the fit is right, you’ll feel it. Communication is clear. Support is fast. Issues get solved the first time. And your technology finally becomes an asset, not a liability.

Once you’ve decided it’s time to upgrade your IT, whether that’s outsourcing for the first time or replacing a patchwork system that’s held together with duct tape and crossed fingers, the next big question is: How do we actually do this without breaking things, confusing our team, or creating more chaos?

A well-run transition should feel like a sigh of relief and here’s how to make that happen.

Before you can fix anything, you need to know what you’re working with. A good IT provider will start with a thorough audit of your:

• Devices and endpoints
• Operating systems
• Software licenses
• Network and backups
• User accounts and permissions
• Security posture
• Workflow bottlenecks

This will go beyond the technical issues and give you a snapshot of where you are today so you can build a plan for where you want to go.

Got someone on staff who’s been your unofficial “IT go-to”? Bring them in early. They know where the skeletons are buried (digitally speaking), and they’ll be instrumental in making sure the transition is smooth.
You’ll also want to:

• Let your team know what’s changing and why
• Set expectations for who to contact for support going forward
• Encourage feedback during the transition process. Small annoyances add up fast if ignored

The goal is to empower your team and give them the tools they need to succeed.

Many companies only realize how exposed they were once they start the switch. That’s not a bad thing, in fact, it’s one of the biggest benefits of outsourcing: you find the gaps before someone else does.
Early onboarding steps should include:

• Rolling out MFA and secure password policies
• Locking down admin access
• Standardizing software tools and permissions
• Backing up critical data (and confirming recovery plans)

Once the fire drills are over and the basics are stabilized, your IT partner should be helping you think ahead. That means:

• Planning hardware upgrades based on lifecycle
• Mapping out future hires and scaling your systems
• Exploring new tools to improve productivity or client service
• Staying ahead of compliance and cybersecurity needs

In short: IT stops being the thing you “deal with” and becomes a system that helps you grow.

The moment you start to ask,
“Can we keep doing this ourselves? Or is it time to bring in some help?”
…you’re already standing at a turning point.

Because here’s the truth: getting professional IT support is about being smart enough to stop reacting to IT problems and start building systems that support your business, protect your people, and help you grow securely and confidently.