The Green Sheet Online Edition
May 12, 2025 • 25:05:01
Street SmartsSM
Are suits still required for sales?
Remember when payment professionals dressed like bankers and dress codes were part of the ISO and agent playbook? There's no doubt employees got into a festive mood on Fridays when they wore polos and khakis to the office. But dry cleaners weren't cheering when businesses began to ditch the suit and tie and make every day a Casual Friday!
Blame it on Honolulu, says workplace.io, a UK-based workspace provider, noting "Aloha Fridays" began in the 1940s and rapidly spread to other states. "Over time the occasion has spread to the rest of the world, and has no doubt become more prevalent due to increase in evidence that employers should attempt to proactively increase staff morale."
Fashion-forward fintechs
After decades of struggling to reimburse staff for travel and commuting, businesses began to encourage employees to work from home, a trend that accelerated during the Covid pandemic. Over time, business owners eased into casual dress, with tieless, partially open dress shirts and turtlenecks layered under suit jackets.
Before long, tennis shoes and dockers began to replace wingtips and oxfords. And the tech boom poured gas on the fire as younger business owners and tech company giants sported T-shirts and gym clothes at the office.
My advice to anyone who wants to project a casual but professional image would be to wear a logo polo. If you walk into a business in a suit and tie, 99 times out of 100, you will be overdressed.
Twenty years ago, when bankers were our biggest competitors, we dressed like bankers. Today, fintechs are our competition and they wear T-shirts and polos—and some skip the dress code entirely because they’re not even human. Yes, we occasionally compete with automated robots that don't even answer phones.
KYC, KISS
Want to know what else has changed in 20 years? Our customers' buying habits and priorities. Today’s merchants are more concerned about technology than who is handling their money. Loosely translated, this means two things: know your customer (KYC) and keep it simple (KISS) by thinking about tech first and merchant services second.
Merchant level salespeople (MLSs) need to observe how their customers dress and speak. Even attorneys don't wear suits outside the courtroom. In most cases, wearing a logo on a polo or a button-down logo shirt with no tie is 100 percent acceptable.
If you're anything like me and host mostly virtual meetings, I'd advise against using fake backgrounds. Phony backdrops may have had a moment during the pandemic, but today they just look phony. Most people would rather visit your office than a generic beach with swaying palms, or a high-rise penthouse with a non-breathing cat.
Let them into your environment and let that photo of your kid in a football jersey or that hat you're wearing spark a conversation. Someone on a Zoom call recently asked why the number 22 is printed on my hat and I was happy to explain that 22 is Caitlin Clark's (now retired) number.
Casual mindset
Eighty-five years after it became a thing, I think we can safely say that casual workplace dress is here to stay. I have a client who generates millions of dollars in monthly revenue and wears expensive sweatpants.
Don't be shocked by younger businesspeople's casual attitudes, tattoos and playful office environments. Sure, they're having fun, but don't be fooled. They're as serious as we are when it comes to meeting deadlines, quotas and KPIs.
When I ask prospects who are 30 to 60 minutes away from my office if they'd like to drop by or meet virtually, most of them choose to meet online. People of all ages and backgrounds find virtual meetings are faster and more efficient, but I always give them the choice.
It's important in sales to create a level playing field for you and your prospects. If you're the only person wearing a suit and tie in a room full of T-shirts, hoodies and sweatpants, what are your chances of closing that deal?
While everyone has an opinion on what to wear on a sales call, I can confidently say that dressing down has not hurt my business. If anything, it has made this 64-year-old more relatable and less of a dad to a younger clientele.
Want to know more? Keep reading The Green Sheet and consider following me on LinkedIn, where we can share ideas and support each other. 
Allen Kopelman, a serial entrepreneur, is co-founder and CEO of Nationwide Payment Systems Inc. and host of B2B Vault: The Biz to Biz podcast. Email him at allen@npsbank.com and connect on LinkedIn https://www.linkedin.com/in/allenkopelman/ and Twitter @AllenKopelman.
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