Blog / hiring
When a growing business needs its first IT person
The signals that a growing business is ready for its first IT hire, why a generalist should come first, and the alternatives worth weighing.
Somewhere between ten and fifty employees, most businesses hit the same wall. The owner is still resetting passwords. The "computer person" is whoever in accounting seems least afraid of the router. Projects stall because nobody owns them, and every technology decision is made by the vendor proposing it.
The question I get at this stage is usually phrased as "is it time to hire an IT person?" The honest answer is: sometimes, and later than most people think, and almost never the IT person they have in mind.
The signals that it is actually time
Headcount alone is a poor trigger. I have seen sixty-person companies run beautifully on outsourced IT and fifteen-person companies drowning without it. The real signals are about load and risk.
Someone senior is losing real hours to IT. When an owner or a manager spends five or ten hours a week on support and vendor-wrangling, you are already paying for IT, just at the most expensive hourly rate in the building.
Technology decisions are being made by default. Renewals auto-renew, vendors upsell unopposed, and nobody can say what the company spends on software in a year. That silence is expensive, for the reasons I laid out in what a second opinion actually catches.
Risk has quietly outgrown the setup. You are handling customer data, or a day of downtime now costs real money, or an insurance or compliance questionnaire has landed that nobody can answer. Backups nobody has ever tested belong in this category too.
Growth is on the calendar. A second location, a big hire wave, a new system. Any of these is far cheaper with an owner on the inside.
Two or more of those, and it is time to put someone in charge of technology. Whether that someone is an employee is a separate question.
Hire the generalist first
When companies do hire, the classic mistake is hiring a specialist for whatever hurt most recently. The network was down twice, so they hire a network person, who then spends four days a week on password resets, laptop setup, and printer exorcisms, and leaves within the year.
Your first IT person should be a generalist: comfortable with helpdesk work but able to manage vendors, run a small project, ask hard questions about a quote, and write things down. The writing matters more than people expect. The first hire's lasting contribution is usually documentation and process, an inventory of what exists, who has access to what, and what to do when things fail.
Title it accordingly. You are not hiring a systems architect; you are hiring an IT manager or IT generalist who owns the whole messy surface. Specialists come later, or come rented.
The other half of the generalist-first rule: do not expect strategy and support from the same seat on day one. A good generalist keeps the lights on and makes vendor management sane. Expecting them to also chart a three-year technology roadmap in their spare time is how first hires burn out.
The alternatives, honestly
A full-time hire is not the only shape this takes, and for many businesses it is not the best one.
Managed services. A good MSP gives you helpdesk coverage, monitoring, and patching for a monthly fee that is usually well under a salary. The trade-off is incentives: an MSP is also a vendor, and the recommendations that reach you will lean toward what the MSP sells and supports. MSPs are excellent hands. They are a conflicted brain.
Fractional IT leadership. The piece an MSP cannot honestly provide, someone on your side of the table making decisions, does not need to be full-time. A day or two a month of independent oversight covers vendor management, budgeting, and the quote reviews and project scoping that keep the MSP honest. This is a large part of my own practice, on a monthly retainer.
The combination. The pattern I recommend most often to companies under about forty people: an MSP for the hands, a fractional lead for the head, and the first full-time hire deferred until the support volume genuinely fills a week. When that hire finally happens, they inherit documentation and working vendor relationships instead of chaos.
Deciding
If technology has become a job at your company and nobody holds it, the worst option is the current one, where it belongs to everyone and no one. Whether the answer is a hire, an MSP, a fractional arrangement, or some mix depends on your support volume, your risk, and your growth plans, and that is a conversation I have with owners regularly. If you are weighing it now, my fractional IT leadership page describes how I fill that seat, and a short conversation will usually tell you which shape fits.