Shaun McDonald is the Director of Customer Success at Harri, a New York-based technology company founded in 2012 that helps restaurants, hotels, and hospitality businesses hire, schedule, and engage frontline employees. Harri serves millions of workers across tens of thousands of locations worldwide and counts McDonald's, Subway, Burger King, Raising Cane's, and Shake Shack among its clients. Shaun came up through restaurant operations as a general manager at Sweetgreen and Luke's Lobster before moving into hospitality SaaS through Restaurant 365, where he earned a promotion within his first year and discovered that the gap between restaurant operations and tech was far smaller than he expected.
✨ Key Insights You'll Learn:
Started as a dishwasher and bus boy in college before transferring to Johnson and Wales University to complete culinary and business degrees
General manager at Sweetgreen and Luke's Lobster, where he once ran a new store opening entirely alone after his full staff called out
Moved to Restaurant 365 after seven-plus years in restaurants, renting an RV with his then-girlfriend and driving cross-country before either had secured a job
Joined Harri after being recruited out of Restaurant 365, drawn to customer success over reactive support work
Harri's platform covers the full employee lifecycle from applicant tracking through scheduling, timekeeping, onboarding compliance, and employee engagement
Fair Work Week compliance automation: helping operators avoid tens of thousands of dollars per week in penalties as city-level regulations expand
California break law as a top client acquisition trigger: operators get sued, lose their vendor, then find Harri
Harry Engage: clock-in touchpoint delivering surveys, training, and recognition at the moment employees have to interact with the system, driving response rates into the 70-90 percent range
One-click AI scheduling in beta: agentic flows checking forecasts, local events, employee availability, and skill levels simultaneously to produce a complete schedule with a single button press
Misdiagnosed with blood cancer at 23, spent over a year getting bone marrow tests before a specialist cleared him — an experience that reoriented his relationship with gratitude
🌟 Shaun's Key Mentors:
Restaurant Operations Career (Dishwasher to GM): Eight-plus years of frontline experience that gave Shaun the operational credibility to consult enterprise hospitality clients as a peer, not a vendor
Restaurant 365 (Early SaaS Career): Showed him that everyone in tech is figuring it out too, earned a promotion in under a year, and connected him to the tight-knit hospitality SaaS community
The Luke's Lobster Employee He Promoted to GM: A young woman from South Boston who never thought she'd amount to anything, whose journey from crew member to store manager is the moment Shaun most wants to be remembered for
All In Podcast (Ongoing Learning): Chamath Palihapitiya, David Sacks, and the other hosts provide real-time visibility into what cutting-edge AI companies are doing, helping Shaun stay at the edge rather than chasing from behind
👉 Don't miss Shaun's account of running a restaurant opening entirely alone, the cancer misdiagnosis he kept from almost everyone for years, and why hospitality is the best possible training for a career in customer success.