Our 40 Under 40 Class of 2026 is made up of digital natives who don’t get wowed easily. But being fluent in technology doesn’t mean betting on it. So, when they admit a product won them over despite their skepticism — and operators made them believers — it’s worth paying attention.

Hardware skeptics: smart coolers

Today’s under-40 leaders are younger Millennials and Gen Z — generations with deep digital roots, mobile-first habits and expectations for tech-enabled work. Yet being digitally fluent does not mean that each tech option is equally valuable. The most successful offerings deliver real value worthy of any tradeoffs in workflow.

“One product that surprised me was AI-powered smart coolers. Early on, my skepticism wasn’t around the technology itself — it was around the idea of operators having to manage yet another segment of their business on a separate platform,” said Adam Cook, director, OEM and channel sales at Cantaloupe Inc., now part of 365 Retail Markets. “What changed my perspective was the willingness of many AI smart cooler brands to integrate directly into Seed Markets. That enabled operators to manage traditional vending, micro markets and AI smart coolers from a single platform instead of creating additional operational complexity. Combined with the frictionless consumer experience and strong operational visibility, it became clear how impactful the technology could be when integrated correctly. It reinforced how important operational simplicity is when introducing new technology into the unattended retail industry.”

Eliran Vaknin, chief product officer and U.S. site manager at Shekel NA Inc., also overcame early skepticism.

“When we first [added weight-based] AI shelves into the Innovendi elite smart coolers, I was skeptical the market was ready. Unattended retail operators are practical people. They care about uptime and margins, not technology for its own sake. I worried the ‘smart shelf’ concept would feel like overengineering for what operators saw as a simple grab-and-go transaction,” Vaknin said. “But it completely won them over. The fact that the cooler autonomously knows exactly what was taken, by whom and when, without any manual scanning or intervention, turned out to be a game-changer for operators managing dozens of locations remotely. What I thought was a hard sell became the feature that closes deals.”

Not every surprise hit starts with doubt. Sometimes, it’s simply a feature that outperforms expectations. Michael Wood, senior manager, product management at 365 Retail Markets, saw that firsthand.

“We launched a new spotlighting function on our Smart Vision store platform to promote key products on our device UI, hoping it would be adopted well by the market in time,” Wood said. “We’ve seen significant adoption, and our customers love it!”

The pattern holds beyond hardware. Even data tools — which operators theoretically want — can fail if the interface doesn’t earn its place in the workflow.

Data and dashboards

Data analytics and dashboards are essential tools for operators, but not all dashboards are effective. Cluttered interfaces, poorly selected metrics or poor user experience can cause an otherwise sound product to fail. Technology providers that take care to build a solid interface can avoid the fate of a failed product.

“When CPI introduced enhanced machine‑level reporting through our cashless platform — especially the detailed transaction‑level insights — I initially thought it would be underused. Many operators were already overwhelmed with data, and I assumed they wouldn’t want ‘one more dashboard’ to manage,” said Ana Martins, customer service team leader at Crane Convenience. “But the opposite happened. Customers quickly realized how powerful the insights were for spotting patterns, identifying underperforming machines and understanding peak usage times. What I expected to be a niche feature became something operators relied on daily to make smarter operational decisions.

“It was a great reminder that customers don’t just want data — they want clarity,” Martins added. “When information is presented in a way that genuinely helps them run their business better, adoption follows naturally.”

Market timing and platforms

For founders, the question is rarely just whether a product works. It’s whether the market is ready for it. Two founders shared how that truism played out for their companies.

“Of all our products the last 12 years, I don’t think we deliberately built any thinking that they would fail and got lucky or surprised — haven’t had that luxury at least!” said Evan Jarecki, co-founder and CEO of Gimme. “The closest experience to answer this comes from our product: Gimme VMS. For years after launching Gimme in 2014, we said we would never build a VMS. They were robust, super complex, lots of moving parts, and there were already several major players in the space.

“It wasn’t until we had a group of eight (very determined) operator customers literally pre-pay us to build a VMS that we finally decided to go down that path. They became the first (much-needed) beta customers and referred us to several other operators over the years,” Jarecki explained. “And now, approximately eight years later, after kicking off the development effort, we have a mature VMS in the market with so much room to grow through helping operators. I think we’re still being surprised — to this day — with the need for a good VMS to help operators save time, make good decisions, make more and save money.”

Patrick McGinty, founder of VendVue, was confident in the technology behind his sales-enablement platform. The real question: Were operators ready to embrace it?

“Honestly, one thing I thought could fail was our outbound sales engine for the unattended retail industry. When I started VendVue, most operators were used to waiting on referrals, RFPs or traditional ‘locator’ style services. The idea that a company could build a true outbound sales engine focused specifically on securing high-value vending, micro market and coffee service opportunities at scale was something a lot of people doubted. Even I questioned whether the industry would embrace it,” McGinty said.

“What surprised me was how fast operators started seeing results once we built the systems correctly. We realized there was a massive gap in the market between operators who were great at operations and operators who had a predictable way to generate new business,” he explained. “What started as an experiment turned into a nationwide sales platform generating opportunities across manufacturing, healthcare, education, hospitality and multifamily housing. It completely changed the way I look at the future of unattended retail growth.”