One of the most common questions I hear from growing business owners is: "When should I hire my first IT person?"

It's a tough question because the answer isn't "when you have 50 employees" or "when your revenue hits $2M." The right time depends on your specific situation—and making the wrong decision can either waste money or leave you dangerously exposed.

In this post, I'm sharing the framework we use at Sandbar Systems to help business owners decide whether—and when—to make a first technology hire.

Why This Decision Matters So Much

Your first IT employee (or contractor, or fractional leader) will set the tone for how technology gets handled for years. A bad hire creates technical debt and bad habits. A good hire prevents security disasters, reduces downtime, and actually saves money.

Yet many business owners approach this casually: "We're growing, so let's hire an IT person." Without clarity on the role, the skill level needed, or whether they actually need a full-time person, this often backfires.

The Three Phases: When You Need What

Let me break down when to hire IT based on company size and complexity:

Phase 1: DIY + Outsourced Specialists (0-20 Employees)

At this stage, you probably don't need a dedicated technology person. Instead:

  • You or your office manager handles basic stuff: creating user accounts, password resets, basic troubleshooting
  • Outsourced specialists handle: network installation, backup setup, security configuration
  • An MSP (Managed Service Provider) monitors systems 24/7 and handles emergencies

This keeps costs low and ensures actual technical decisions are made by experts.

Cost: $500-$2,000/month for MSP + occasional project work Downside: You're dependent on external vendors for everything

Phase 2: Part-Time or Fractional IT (20-50 Employees)

This is where most businesses first need dedicated technical leadership. But "full-time IT person" isn't usually the right answer yet.

What you actually need is:

  • Strategic technology leadership: Someone who understands your business and plans your tech roadmap
  • Security and compliance: Ensuring you're following best practices, not just reacting to problems
  • Vendor management: Someone who evaluates, negotiates with, and oversees your MSP and other tech vendors
  • Policy and documentation: Creating standards for how technology is used in your company

This is perfect for a fractional CTO—someone who works 10-20 hours per week helping you make the right technology decisions and manage your MSP.

You're not paying them full-time salary ($120K-$200K), but you're getting C-suite level guidance on your technology strategy.

Cost: $2,500-$5,000/month for fractional CTO + $1,500-$3,000/month for MSP Benefit: You have executive-level tech leadership without the salary burden

Phase 3: Full-Time Technical Staff (50+ Employees)

Once you hit 50+ employees and significant complexity, you probably need someone on-site full-time who:

  • Manages your MSP day-to-day and handles urgent issues
  • Handles hardware, software, and infrastructure decisions
  • Works alongside your fractional CTO (if you keep one) on strategy

This person is often a network administrator or systems administrator—not a CTO. They're the executor, not the strategist.

Cost: $60K-$90K salary + benefits Benefit: On-site support, faster incident response, deeper institutional knowledge

How to Know It's Time to Hire

Here are the concrete signals that you need your first IT employee or fractional tech leader:

You're spending 2+ hours per week on IT issues yourself. Your time is too valuable. It's time to outsource or hire.

Your current MSP isn't meeting your needs. A fractional CTO can help you evaluate, change vendors, and oversee the relationship better.

You have compliance or security concerns. You need someone who understands your industry's requirements and builds systems that meet them.

Technology decisions are being made reactively. You're always responding to crises instead of planning ahead. A fractional leader can change this.

You're worried about a key person's departure. If your accountant or office manager leaves and they're the only one who knows all your passwords and systems, you have a problem. You need documentation, structure, and shared knowledge.

Your team is growing beyond 30 people. At this point, the complexity justifies dedicated tech leadership.

The Wrong Approach: "Let's Hire an IT Person"

I see this mistake constantly. A business owner decides they need an IT person, posts a job for "IT Support" or "Network Administrator," and hires the first person who applies.

The problem? They haven't defined:

  • What the person actually needs to do
  • What skills matter most
  • Whether they need full-time or part-time
  • What success looks like
  • Who this person reports to

Here's what often happens: They hire someone who's great at basic support (password resets, printer troubleshooting) but has no strategic vision. Three years later, the business has outgrown that person. Or they hire someone overqualified for the work, they get bored, and they leave.

The Right Approach: Start with Strategy

Before you hire anyone (even part-time), ask yourself:

What decisions do I want technology support with?

  • Network and WiFi design
  • Cloud platform choices (AWS, Microsoft, etc.)
  • Cybersecurity and data protection
  • Growth planning for infrastructure
  • Vendor relationships

Who owns technology decisions in my company right now?

  • If it's you, and you're not an IT person, you need help
  • If it's your accountant or office manager, they need backup

What am I paying for now in fragmented ways?

  • Multiple vendors with no coordination
  • MSP services but no strategic oversight
  • Consultants who don't work together
  • Emergency response instead of prevention

Once you've answered these, you know whether you need:

  1. A fractional CTO (10-20 hours/week, $3K-$5K/month) to provide strategic leadership and vendor oversight
  2. A better MSP with 24/7 monitoring and documented SLAs
  3. A part-time IT person ($20K-$30K/year) for hands-on support while a fractional leader handles strategy
  4. Eventually, a full-time administrator once you hit 50+ employees

The Role of a Fractional CTO

Since this is an option many growing businesses miss, let me explain what a fractional CTO actually does:

A fractional CTO is an experienced technology executive who works part-time to:

  • Audit your current technology and identify risks
  • Create a technology roadmap aligned with your business goals
  • Evaluate and select vendors (networks, cloud platforms, security tools)
  • Manage your MSP relationship and hold them accountable
  • Build technology policies and standards as you grow
  • Prepare you for scale before you face a crisis

They're not doing the day-to-day technical work. They're making sure the day-to-day work is being done correctly.

For a growing business, this is often the perfect first technology hire—and it costs far less than a full-time CTO ($250K+/year).

Red Flags When Interviewing

If you do hire someone for a technology role, watch for these red flags:

  • They can't explain technical concepts simply. If they can't help you understand the "why" behind decisions, they're not right for your business.
  • They focus only on problems, not prevention. Good technologists think in systems and prevention, not just reactive fixes.
  • They have strong opinions about technology but no business sense. They need to understand your business constraints and goals, not just what's technically cool.
  • They can't account for all their previous employers/gaps. In tech, reliability and trustworthiness matter hugely.
  • They haven't worked in environments similar to yours. A startup CTO and a manufacturing company IT manager need very different skills.

The Real Investment Needed

Whether you hire someone or work with a fractional leader, budget for:

  • Salary or fractional fee ($2,500-$5,000/month for fractional; $5,000-$7,500/month for part-time; $5,000-$7,500/month for full-time)
  • Tools and monitoring software ($200-$500/month)
  • Professional development ($500-$1,000/year)
  • Backup and security infrastructure ($300-$1,000/month)

Total: Start with $3,500-$6,500/month for a fractional CTO + MSP setup. Compare that to the cost of a data breach, ransomware attack, or prolonged downtime. The ROI is enormous.

Getting This Right

The businesses we work with as fractional CTO partners usually move through this progression:

  1. Start: Managed service provider for basic support + fractional CTO for strategy
  2. Growth: Add part-time IT person for on-site support
  3. Scale: Hire full-time administrator or IT manager

At each stage, they have clear technology strategy and strong vendor relationships—not a patchwork of reactive decisions.

Ready to Build Your Technology Team?

Sandbar Systems provides fractional CTO services for growing businesses. We'll help you audit your current situation, create a technology roadmap, and decide whether you need a part-time hire, a fractional leader, or both.

Schedule Your Free Consultation

Call us: (804) 510-9224 Email: info@sandbarsys.com

With 15+ years of experience helping hundreds of businesses build their technology foundations, we know exactly what works at each stage of growth.