Inside a restaurant, long before a guest ever walks through the door, another kind of pressure is already building. It lives on spreadsheets, in labor targets, in half-finished schedules rewritten late at night. For managers, staffing is rarely about hospitality. It is about survival.
That tension is exactly what Will Stewart, founder and CEO of rightwork, is trying to remove.
Stewart joined Shawn Walchef on Digital Hospitality to talk about how operational complexity, human behavior, and modern technology collide every day inside restaurant labor decisions, and why better systems can unlock calmer teams and better guest experiences.
Taking Action
For Stewart, the problem was never abstract. It was learned on the floor.
Before founding rightwork, Stewart spent years inside the Starbucks ecosystem, where every decision about labor, layout, and process was magnified by scale. Small inefficiencies did not stay small. They multiplied across thousands of stores, millions of transactions, and countless employees.
At Starbucks, Stewart learned how much rigor goes into decisions guests never notice. Store layouts tested like engineering puzzles. Stations measured, timed, reconfigured. Data mattered. But what stood out most was what data alone could not solve.
“Human factors are real,” Stewart explained. “You can design the perfect plan, but once you put people into it, things change.”
Schedules broke. Demand shifted. A single disruption could unravel a day. Managers were expected to hit labor targets without the tools to do so confidently. The pressure landed on people, not systems.
That gap stayed with him.
The Origin Story
rightwork did not begin as a startup pitch or a venture thesis. It started as a practical response to a familiar ask.
After leaving Starbucks, Stewart was approached by a former operator running a growing restaurant group in the Pacific Northwest. The question was simple: could Stewart build something similar to the labor modeling tools he had worked on at Starbucks, but scaled down for an emerging brand?
Instead of consulting, Stewart made a different choice.
He asked the operator to become a design partner.
That collaboration became the foundation of rightwork. A labor modeling and forecasting platform designed to help managers answer a basic question with confidence: how many people do we need, doing what, at what time?
Not to cut corners. Not to squeeze teams. But to align labor with reality.
Early on, Stewart recognized a pattern across restaurant groups. Corporate leaders set labor targets. Managers were held accountable for missing them. Yet the tools connecting those expectations to day-to-day scheduling were either outdated, overly manual, or disconnected from actual demand.
rightwork was built to close that gap.
Where Technology Meets Trust
Labor scheduling is not just math. It is trust.
Managers want control. Leaders want consistency. Teams want fairness. And guests want seamless service. Stewart believes the future lives in the space between automation and human judgment.
rightwork approaches AI not as a replacement for managers, but as a co-pilot. The platform can generate full schedules, suggest adjustments, or fill gaps dynamically as availability or demand changes. Managers can accept recommendations, override them, or guide the system based on what they know locally.
“The goal is confidence,” Stewart said. “No manager should walk into a shift unsure if they staffed it correctly.”
By shifting repetitive, time-consuming work into software, rightwork gives managers space to focus on people, coaching, and service. Technology handles complexity so hospitality can take center stage.
Digital Hospitality, Defined
For Stewart, digital hospitality is not guest-facing first. It starts behind the scenes.
When administrative burden shrinks, teams breathe easier. When schedules align with demand, stress drops. When managers trust their tools, they show up differently for their teams and their guests.
“Technology should be in service of humans,” Stewart said. “It should make their jobs easier, not louder.”
That philosophy runs through rightwork’s design. From labor modeling to scheduling to training and forecasting, the platform is built to simplify decision-making, not overwhelm it.
Why We Love Digital Hospitality
rightwork’s vision stretches beyond schedules. Stewart sees an opportunity to build an operating system for decision-making inside restaurants, one that blends data, AI, and lived experience into clear guidance for managers at every level.
But growth is intentional. The company has expanded primarily through word of mouth, prioritizing customer trust over blitz scaling. Stewart remains deeply involved in onboarding, training, and feedback loops, believing that staying close to operators is the only way to build tools that truly work.
At its core, rightwork reflects the same truth Digital Hospitality exists to explore. Better technology does not replace hospitality. It protects it.
When systems work, people can focus on people.
And that is where hospitality lives.
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