I’m a tech CEO. Here’s why my employees are required to work a restaurant shift

When I tell fellow tech executives that every employee at sunday, from our engineers to our finance team, must complete a restaurant shift before they can fully onboard, I usually get confused looks. “You mean like, shadow someone?” they ask. No. I mean they tie on an apron, take orders, run food, and yes, deal with the 15-minute wait for the check that our product was literally built to eliminate.

It sounds extreme. It is extreme. And it’s also one of the smartest business decisions we’ve made.

Here’s why: business is often removed from the industries we serve. We’re keeping that empathy right there.

The Empathy Gap in Tech

I’ve spent 25 years in the tech world, scaling e-commerce unicorns in Europe before cofounding sunday. I’ve seen brilliant engineers build elegant solutions to problems they’ve never personally experienced. I’ve watched product teams debate restaurant workflows they’ve only seen in wireframes. The result? Products that work in theory but fail in the chaos of a Friday night dinner rush.

Using our industry as an example, the restaurant space can’t be disrupted from a distance. It’s intensely human. A server manages six tables, remembers who wanted dressing on the side, tracks which kitchen orders are running late, and still needs to radiate warmth when checking on the anniversary couple at table twelve. When we ask them to adopt new technology, we’re not just changing their workflow, we’re asking them to trust us with their tips, their table turn times, and their relationship with guests.

You can’t design for that kind of stakes without understanding them viscerally.

What a Saturday Night Shift Teaches a Software Engineer

Last month, I watched our newest engineer finish his restaurant shift at one of our partner locations. He was confident going in; he understood our API integrations, he knew our payment flow inside and out. But after five hours on his feet, he had a revelation.

“At the end of my shift, I had to manually enter tips from 22 tables into the POS system,” he told me, exhausted. “Twenty-two times typing in amounts, double-checking I got the numbers right, worrying I’d accidentally shortchange myself or mess up the restaurant’s accounting. The whole time I’m thinking about the train I’m about to miss, and I’m doing math in my head to see if my night was even worth it. It took 15 minutes of my life I’ll never get back.”

This wasn’t theoretical anymore. “I finally understood what we’re actually saving people from,” he told me the next day. “It’s not just 15 minutes—it’s the mental load of worrying you made a mistake, the frustration of doing data entry when you’re exhausted, the indignity of technology making your life harder instead of easier. When I use sunday now, I know exactly whose time I’m giving back.”

That’s the point. Empathy at scale isn’t built through user research reports. It’s built through experience.

Hospitality as a Business Philosophy

What started as a practical requirement has become central to how we think about everything at sunday. Hospitality isn’t about being nice. It’s about anticipating needs, moving with urgency, and making people feel valued even under pressure.

Those principles translate directly to how we run our business.

When a restaurant partner calls with an issue, our support team doesn’t respond with ticket numbers and SLAs. They respond like servers handling a complaint: with immediate acknowledgment, genuine concern, and a bias toward solving the problem now rather than escalating it later. Our customer success team knows that “I’ll get back to you tomorrow” is the tech equivalent of “your food will be out in a few minutes”—a polite deflection that erodes trust.

We’ve also borrowed the restaurant world’s obsession with the guest experience. In hospitality, there’s no such thing as “that’s not my table.” If a guest needs something, you handle it. We’ve tried to instill that same mentality. When a new market launch hits a snag, our engineers don’t wait for the ops team to flag it. When a sales issue arises, our product managers jump in. We move like a restaurant team during a rush—fluid, collaborative, and focused on the experience we’re creating.

The Metrics That Matter

Here’s what surprised me most: this policy has become one of our best retention and recruiting tools.

We’ve had a 94% retention rate among employees who complete the restaurant shift program, compared to 78% at my previous tech companies. Employees consistently rank it as one of their most valuable onboarding experiences.

New hires tell us they appreciate working somewhere that values understanding over assumption. They like that leadership doesn’t just talk about customer obsession—we quite literally make them walk in our customers’ shoes (and sensible non-slip ones at that).

And when we hire, the restaurant shift requirement self-selects for people with the right mindset. Candidates who balk at the idea of working a shift often aren’t the right fit for our culture anyway. The ones who light up at the challenge? Those are our people.

The tech industry loves to talk about disruption, but we’re often remarkably detached from the industries we claim to understand. We optimize for what we can measure: clicks, conversions, load times. And we miss what we can’t, the relief on a server’s face when they don’t have to chase down a credit card, the gratitude of a mom who can split a check without asking for help, the pride a restaurant owner feels when their team has more time to create memorable moments.

Making our employees work restaurant shifts isn’t a cute culture quirk or a team-building exercise. It’s a business imperative. Every hour our team spends in a restaurant is an investment in building a product that actually solves real problems, not imagined ones.

A Challenge to Tech Leaders

I’d encourage every tech CEO, especially those building B2B products, to ask yourself: When was the last time you personally experienced the problem your product solves? Not observed it. Not read about it in research. Actually lived it?

If the answer is “never” or “it’s been years,” you have a dangerous knowledge gap. Your team is making decisions based on assumptions, building for personas instead of people, and probably missing opportunities that would be obvious to anyone who spent a day in your customers’ reality.

You don’t need to make it a formal policy like we have. But you do need to close the empathy gap between your builders and your users. Shadow a shift. Take customer service calls. Use your competitor’s products. Do whatever it takes to remember that behind every user statistic is a human being trying to do their job, feed their family, or simply have a nice dinner without waiting 15 minutes for the check.

At sunday, we’ve learned that great technology in the hospitality space doesn’t come from brilliant engineers alone. It comes from brilliant engineers who’ve burned their hand on a plate, forgotten which table ordered the gluten-free option, and felt genuine panic when the payment system hiccups during a Saturday night rush.

That’s not just good culture. That’s good business.