New York Teaches You How to Earn Attention. Chicago Teaches You How to Keep It.

Author: Thomas Murgatroyd (CEO, Cloudcat Recruitment)

“Chicago AEs couldn’t survive in New York.” 🇺🇸 🗽

I’ve heard that one more than once. The logic is always the same: New York is rapid, buyers are tough, competition is relentless.

Chicago, by comparison, is supposedly the softer cousin: relationship-driven, too comfortable, a place where people have been selling to the same accounts for twenty years.

There’s some truth in that.

New York is a city that assumes whatever captured your attention this morning will be replaced by this afternoon.

The restaurant with a six-month waiting list becomes yesterday’s news. The Broadway show everyone was talking about gets eclipsed by the next opening. Even neighbourhoods reinvent themselves every few years.

Ruthless. But that creates sharper messaging, faster qualification and a level of commercial urgency that’s hard not to respect.

Chicago rewards something different.

Many of the companies buying software aren’t chasing the latest trend.

They’re manufacturers, logistics firms, insurers and industrial businesses that have been around for decades.

Leadership teams don’t rotate every eighteen months.

Your reputation follows you from company to company because the market is far smaller than its size suggests.

That’s why I’ve never liked the phrase “relationship selling.”

It makes it sound as though enterprise sales is built on lunches and golf days. It isn’t.

It’s built on credibility. Losing a deal and still getting the next meeting. Having a buyer answer your call eighteen months later because, although they didn’t buy, they trusted the way you sold.

Of course, Chicago romanticizes this too. Plenty of AEs call it “playing the long game” when they’re really avoiding difficult commercial conversations. Relationships don’t replace urgency.

But New York has its own blind spot. It can reward visibility over permanence. You meet incredible sellers with enormous networks, yet surprisingly few buyers willing to spend political capital recommending them internally.

Neither market is better.

One teaches you how to earn attention. The other teaches you how to keep it.

SaaS sales needs both.