Almost every growing organization starts the same way: someone's nephew, a talented office manager, or a one-man IT shop that's been "handling the computers" since the beginning. It works. It's affordable. And then, somewhere between 15 and 30 people, it quietly stops working — usually without anyone saying so out loud.
Here are the signs we see most often, from the organizations that eventually call us.
1. IT problems wait for one person's availability
When your IT depends on a single human, every problem inherits their calendar. Vacation, illness, a bigger client, a day job — your outage waits its turn. The tell: people stop reporting problems because "he's busy," and workarounds become the real system.
What it looks like in a 20-person office: the shared printer has been "acting up" for three weeks, and everyone now prints to the one by the kitchen instead.
What fixes it: more than one person who can pick up a ticket, working from the same queue, so nothing depends on one calendar.
2. Security is nobody's actual job
Your one IT person is fully consumed keeping things running. Patching cadence, MFA coverage, backup testing, email defense — the preventive work that stops incidents — is what falls off the truck first. Nobody decided to skip it. It just never had a scheduled hour.
What it looks like in a 20-person office: MFA is on for the owners, and "we'll get to the rest," and nobody can say when the laptops last took their updates.
What fixes it: security work that runs on a schedule and shows up in a report, whether or not the week was busy.
3. You don't know if the backups work
Ask one question: "when did we last successfully restore something?" If the answer is a story about the backup software rather than a date, you have hope, not a plan. (We wrote more about this on the backup and disaster recovery page.)
What it looks like in a 20-person office: a green checkmark in a console nobody else can log in to, and no one who remembers the last test restore.
What fixes it: test restores on a calendar, with the date and what was restored written down where leadership can see it.
4. Every fix is a mystery novel
No ticket history, no documentation, no asset list — the knowledge lives in one head. That's fine until the head is unavailable, and catastrophic when the head leaves. Institutional memory shouldn't have a single point of failure.
What it looks like in a 20-person office: the Wi-Fi password is on a sticky note, and the admin password for the firewall is "somewhere in his email."
What fixes it: a ticket for every job, a written record of how things are set up, and admin passwords in a shared vault the business owns.
5. Growth creates dread instead of process
A new hire should be a checklist: account, laptop, access, done by Monday 9am. If onboarding is a scramble and offboarding is "we'll get to it" — with former employees' accounts still active — the arrangement has been outgrown.
What it looks like in a 20-person office: the new starter shares a laptop for their first week, and someone who left in the spring can still sign in to email.
What fixes it: one written checklist for starters and one for leavers, run the same way every time, with the leaver's access closed on their last day.
6. The bill is unpredictable — or suspiciously low
Hourly IT means bad tech months are bad budget months. And a suspiciously low retainer usually means preventive work isn't happening at all. Either way, you can't budget for it, and your board or leadership team notices.
What it looks like in a 20-person office: one month's IT invoice is three times the last, and nobody can say what the quiet months actually paid for.
What fixes it: a price tied to what's being looked after, agreed in advance, so a hard month doesn't become a hard invoice.
A quick self-check
Answer these six questions honestly. Each one mirrors a sign above.
- Do IT problems wait until one particular person is free?
- Is security work done only when there's time left over?
- Would it take a phone call to find out when a backup was last restored?
- Does the knowledge of how things are set up live mainly in one person's head?
- Does a new starter or a leaver cause a scramble?
- Is it hard to predict next month's IT bill, or to say what this month's paid for?
Three or more yes answers means it's time to talk.
Three ways forward
There isn't one right answer. There are three common ones, and each suits a different organization.
Hire a second person. The cost driver is salary, plus benefits, tools and training, and the time it takes to recruit and bring them up to speed. It suits organizations with enough steady IT work for two full-time people and the appetite to manage an internal team. We wrote about what goes into that number in the real cost of hiring IT in-house.
Add co-managed support. You keep your IT person and give them a team behind them: shared tools, a shared ticket queue, cover for time off and extra hands for projects. The cost follows what the outside team is managing. It suits organizations whose IT person is good and wants to stay, but is stretched. More on how that works on our co-managed IT page.
Move to fully managed. An outside team takes the whole of IT: support, security, backups, vendors and planning. The cost follows what's being managed: the computers, servers and systems looked after. It suits organizations with no internal IT, or whose IT person is moving on. See managed IT for what that includes.
Common questions
Is it bad to have one IT person?
No. Plenty of organizations are well served by one good IT person for years. The risk isn't the person; it's that everything depends on them being available, and that preventive work gets squeezed out by the day's tickets. The fix is usually support around them, not a replacement.
Can our IT person stay if we bring you in?
Yes. That's exactly what co-managed IT is for. Your IT person keeps the work that depends on knowing your business, we take the overflow, the time off and the routine security work, and the split is agreed up front and written into the agreement.
How do we tell our IT person without it feeling like a replacement?
Bring them in early, before anything is signed, and frame it as what it is: a team behind them. Ask them which parts of the job they'd hand off first. Most IT people who've been carrying a whole office alone are relieved to hear it, and they'll ask the best questions on the first call.
What the next step actually looks like
Outgrowing a one-person arrangement doesn't have to mean firing anyone or hiring a department. For some teams it means co-managed IT — keeping your person and giving them a team, tooling, and coverage. For others it means moving to a managed IT partner with a flat rate, a real security stack, and more than one human.
The honest first step is an outside look. A free IT risk review takes 30 minutes and tells you where you actually stand — security, backups, and single points of failure — whether you work with us or not.