Fix Your Schedules, Fix Your Service! Will Stewart Explains the New Rules of Restaurant Labor

·49 min·4 clips

Will Stewart turned a consulting request into the founding of his labor optimization startup, RightWork.

This episode of Digital Hospitality features host Sean Walsh interviewing Will Stewart, founder and CEO of RightWork, a labor optimization platform for restaurants. Stewart is a former Starbucks operations engineer who applies his background in data and store design to solve complex scheduling problems. The conversation explores how technology can enhance, rather than replace, human decision-making in hospitality. Stewart recounts a scrappy marketing tactic at the National Restaurant Association show, where his startup handed out Starbucks gift cards to generate leads. He details his career path from a Banana Republic sales associate to building simulation tools at Starbucks to evaluate store layouts and labor deployment. His initial work at Starbucks involved creating a "simulation engine" to test the capacity of beverage stations, where he learned the critical importance of qualitative feedback from store "partners." The idea for RightWork crystallized when a former Starbucks operator asked him to consult, leading Stewart to build the product with that restaurant chain as a design partner. A core problem RightWork addresses is the tension between corporate labor targets and a manager's ability to create a workable schedule that accounts for variables like local events or weather. The platform uses AI as a "co-pilot" for managers, offering auto-scheduling logic that can fill shifts while allowing for manual overrides for specific employees. Stewart emphasizes that the goal is to raise the operational floor so every manager can perform at the level of a "superstar unicorn GM." He shares that a key validation moment was when an experienced industry leader from another brand discovered RightWork and asked, "Where have you guys been?" Stewart's philosophy is heavily influenced by Y Combinator's mantra to "do things that don't scale," and he still personally handles customer onboarding and training. The ideal RightWork customer is an emerging, scaling restaurant brand that needs to grow profitably and provide operational visibility to district managers and COOs. He defines digital hospitality as using technology to simplify administrative tasks so employees can focus on serving the customer. His long-term vision is to build an AI-enabled operating system for managerial decision-making that could expand into areas like inventory management. The tone is conversational and story-driven, blending practical business advice with specific technical insights from the restaurant tech space. The style is educational, focusing on the intersection of data analytics and human-centric operations. Restaurant owners, operators, and managers struggling with labor costs and scheduling inefficiency would find immediate value in this episode. Tech founders interested in B2B SaaS for physical businesses will appreciate Stewart's bootstrapped, product-led growth philosophy. Listeners seeking entertainment or narrative drama might find the operational focus too niche.

As heard by us

A practical look at scheduling and forecasting, with AI acting as a manager's co-pilot.

Restaurant labor sits at the center of the conversation here, and the episode stays grounded in the day-to-day problems operators actually face.

Read the full review in PlayNext →

Why you'd press play

If weekly scheduling is eating your manager's time, this gives you a cleaner way to look at the problem.

Read the full recommendation in PlayNext →

Listen to the show on

Apple Podcasts Spotify

Play clips from this episode More from Digital Hospitality