Every week for several years, I drove my kids to swim practice.

Same time. Same route through Lakeview in Chicago.

And every time, right at the intersection of Clybourn and Wellington, it was there.

A wide, skinny billboard stretched across Clybourn staring back at me: a hilariously awkward teenage photo of a boy with braces and a bowl cut.

Below it? A single line: “We’ll help you get through the awkward teenage business years.”

That boy? Isaac Oates, the founder and CEO of Justworks, is using his own middle school mugshot to make a point.

It’s seared in my brain.

I get emails all the time from Rippling, Paychex, Deel, and Bamboo. But when an email from a Justworks rep, I can’t help but smile.

Because in one image and one sentence, they captured something no demo video ever could: That weird stage every growing business hits.

Too big for spreadsheets. Too small for the enterprise expectations. Payroll gets complicated. Benefits become a headache. Compliance starts to matter. A lot.

It’s the hormonal phase of scale. And Justworks nailed their positioning.

They staked a claim in the mind of the buyer. They own a perceptual space. An emotional one.

A moment in the business lifecycle that every leader feels, even if they don’t yet have the language for it.

More than a platitude on a slide deck, this idea lives in the bloodstream of the brand.