Every growing company eventually faces this fork in the road, usually right around the point where the founder or a single overworked generalist can no longer keep up with everything technology-related. The decision that follows shapes a company's operations for years, and yet most businesses make it based on gut feeling or whatever a peer at another company happened to do, rather than a structured comparison of what each path actually delivers.
Step 1: List What You Actually Need, Not What Sounds Impressive
Start by writing down the specific functions technology support needs to cover at your company — help desk response, cybersecurity monitoring, infrastructure planning, vendor management, compliance support. Resist the temptation to write "someone who can do everything." Almost nobody can, and companies that hire for that unicorn job description usually end up disappointed by month three.
Step 2: Price Out the Full Cost of a Hire, Not Just the Salary
A single IT hire's true cost includes salary, benefits, training, the tools and licenses they'll need, and the very real risk of a coverage gap during vacation, illness, or turnover. Add it up honestly. Many founders are surprised to find that a single competent IT hire costs more annually than a comparable outsourced arrangement that comes with an entire team's worth of coverage and expertise behind it.
Step 3: Consider the Breadth Problem
One person, however talented, has a finite skill set. Cybersecurity, network infrastructure, cloud architecture, and compliance are each deep enough specialties that few individuals are genuinely strong across all of them. An outsourced arrangement typically brings a team with varied specialties, which matters more as your infrastructure gets more complex.
Step 4: Think About Continuity, Not Just Capability
What happens when your one IT person leaves, unexpectedly or not? For a solo hire, that's often a period of real vulnerability — undocumented systems, tribal knowledge walking out the door, a scramble to hire and onboard a replacement while things quietly degrade in the meantime. A properly structured outsourced relationship doesn't have this single point of failure built into it.
Step 5: Weigh the Relationship and Context Factor Honestly
The strongest argument for an internal hire is context: someone embedded in your company, in the room for planning conversations, who knows your business without needing it explained. This is real and shouldn't be dismissed. The counterargument is that a well-structured outsourced arrangement, with a dedicated account manager and consistent points of contact, can approximate a good deal of that context over time — just not instantly.
Step 6: Consider a Hybrid Model
For a lot of growing companies, the honest answer isn't fully in-house or fully outsourced — it's a hybrid, where an internal person or small team handles the highest-context, most business-specific work, while a managed IT partner handles the deeper technical bench, after-hours coverage, and specialized security expertise that would be expensive and impractical to build internally. This model tends to scale more gracefully than either extreme as headcount grows.
Step 7: Revisit the Decision as You Grow
The right answer at 20 employees isn't necessarily the right answer at 80. What starts as a reasonable solo hire can become an unsustainable bottleneck as complexity grows, and what starts as a fully outsourced arrangement might eventually justify bringing certain functions in-house. Build a habit of revisiting this decision annually rather than assuming whatever you set up early stays right forever.
Making the Call
There's no universally correct answer here — only the answer that fits your company's size, complexity, and risk tolerance at a given moment. The mistake most companies make isn't picking the "wrong" model; it's picking a model once and never revisiting whether it still fits as the business changes around it.
