On a recent episode of The Creative Stack, Megan and Georg sat down with Stephen Kaupp, Valiant’s chief operating officer, for another installment of the Back Office series. Stephen’s career started about as far from IT as you can get: turning around aircraft at JFK for Lufthansa, with just under two hours to unload, refuel, and reload a plane before it went back out. But the theme underneath everything he’s done since, financial services operations, fractional COO work, and now ten years running Valiant’s back office, has stayed the same. It’s all work that’s invisible until it isn’t.

“I Just Need a Laptop”

Stephen’s favorite example of how people underestimate operational complexity: two friends start a company, get laptops, and work out of Starbucks. It’s simple, because Starbucks already solved the Wi-Fi, the electricity, and the coffee. The moment that company hires its fiftieth employee and moves into an office, all of that infrastructure has to come from somewhere, and most founders haven’t thought about any of it until it’s suddenly their problem.

It’s the same blind spot we see from the technology side. People don’t think about what applications are running, whether they’re secure, how a laptop gets provisioned and later recovered when someone leaves, until the day it becomes urgent.

The Near Miss

Stephen was candid about how he ended up at Valiant full time. Before joining, he’d send referrals Georg’s way and the two would catch up over lunch. On one of those lunches, Georg asked him to stop by the office, because things weren’t going well. At the time, one person was handling everything behind the scenes for a company of 25 to 30 technicians: payroll, insurance, banking, receivables, payables. That person got overwhelmed, understandably, and Valiant found itself with unpaid vendors and unbilled clients.

The fix took Stephen and Georg the better part of a year, working through vendor relationships one at a time. The lesson that stuck: communication saved the situation. Vendors who’d gone unpaid became more forgiving once Valiant was transparent about what had happened and consistent about fixing it going forward.

What’s Actually Changed Behind the Scenes

Stephen has watched the back office evolve in ways that are easy to take for granted. Paper checks gave way to Bill.com. A credit card machine sitting on someone’s desk gave way to secure payment links. Petty cash boxes with a five dollar withdrawal logged on a scrap of paper are gone entirely, replaced by expense cards issued to every employee who might need to expense a subway ride. None of these changes happened because they were exciting. They happened because the old way created risk, and the new way removed it.

Why One-Stop Shops Don’t Always Work

Stephen pushed back on a trend he’s seeing: payroll companies that now also offer IT support. His analogy: a car dealership selling you tires and a car wash makes sense, because it’s all still automotive. A payroll company doing tech support doesn’t have the same logic behind it. Consolidating vendors for convenience can work, but only when the provider genuinely understands the second function, not when it’s a bolted-on upsell.

The same logic runs through how Valiant thinks about its own vendor relationships. Coordination matters, but so does making sure the specialist you’re working with is actually a specialist.

What Stays In-House

Asked what shouldn’t be outsourced, Stephen’s answer centered on anything that touches staff directly. Valiant contracts with an outside firm for its 401k plan, for example, but stays involved in making sure employees have the information and tools they actually need, rather than just handing them a phone number and stepping away. The specifics vary by company, but the principle holds: outsourcing a function doesn’t mean disappearing from it.

Three Things Worth Paying For

Stephen closed with three habits he’d recommend to any growing company. Build in redundant internet service from two separate providers, so a failure in one doesn’t take the business offline. Keep a rolodex of trusted professionals, real estate brokers, HR attorneys, specialized counsel, who aren’t on retainer but who you can call before a big decision, just for a sanity check. And don’t cut corners on the small stuff. Professional cleaning, decent coffee service, and small productivity tools all cost money, but the real question isn’t the price. It’s what you get back in time and morale on the other side of it.

The Takeaway

The businesses that run smoothly aren’t the ones with the fewest moving parts. They’re the ones where someone is paying attention to all of them, even the ones nobody else in the building thinks about.unication informs people, great communication builds trust, and trust is every organization’s most valuable asset

The Creative Stack is produced by Valiant Technology, a managed IT services provider based in New York specializing in serving creative agencies and PR firms. Listen to episodes at podcast.thevaliantway.com and learn more at thevaliantway.com.