Why I Left Enterprise IT to Work With Small Businesses

Nobody at a big tech company ever decided to ignore small businesses.

Nobody had to. It just happens.

I spent 25 years inside Dell, Microsoft, Unisys, and Apple. Great companies, great training, and the same pattern everywhere I looked:

Big vendors often assume a small business wants a shrunken enterprise product. It doesn't. A 10-person firm doesn't need less enterprise. It needs different.

Success gets measured in survey scores averaged across millions of customers. At that scale, one small firm's frustration rounds to zero.

Meanwhile, the best parts of my career were the opposite of that. Sitting next to someone at their desk, learning how they actually use technology day to day. That is where the real work is.

Here's the part that surprised me most: even the local IT providers who say "small business" often mean 50+ employees. Many have minimums a 6-person firm falls below.

So the true small business fends for itself. The office manager becomes the accidental IT person. And honestly? Those office managers are heroes. They keep businesses running with no training, no budget, and no backup. They deserve backup.

I left enterprise IT to work for exactly those businesses. I wrote about why, including the Apple story that first made the problem impossible for me to unsee.