Team Bios

Richard's career spans three decades at the executive level of the hospitality industry. He has served as General Manager, Director, Chief Financial Officer, and Asset Manager — giving him an unusually complete understanding of hotel operations, from guest experience and brand standards to financial performance and asset value.

He holds a General Manager Program certification from Cornell University, an Advanced Revenue Management certification from Cornell University, a Revenue Management certification from HSMAI, and an accounting certification from HFTP. This combination of operational depth and financial rigour is what distinguishes his approach to mystery shopping evaluation — assessments are grounded not just in service quality, but in their direct impact on revenue, reputation, and asset performance.

Richard has conducted mystery shopping engagements on behalf of hotel owners at some of the most storied properties in South Florida, including the Ritz Carlton Resort South Beach (owner Alfredo Lowenstein), the Ritz Hotel on Collins Avenue (owner), the Raleigh Hotel (owner John Cashman), the Marseilles Hotel (owner Lloyd Mandell), the South Seas Hotel (owner Don Glassie), the Deauville Beach Resort (Belinda Meruelo), the Surf Comber Hotel South Beach (owner Jay Mereli), Doral Resorts (owner Bill Kaskel), and The Sagamore Hotel (owner Mark Gardner).

His evaluations are trusted by hotel owners precisely because he has sat in their chair. He understands what owners need to know, what managers are likely to obscure, and what a genuinely exceptional — or genuinely deficient — guest experience looks like from the inside.

Gregory J. Hillary is a seasoned hospitality and property management professional whose career spans some of the most respected names in the industry — from Wyndham Destinations and Starwood Vacation Ownership to Best Western International and the iconic Arizona Biltmore Resort. With over 16 years of General Manager experience, Gregory has led hotels, resorts, and vacation rental portfolios across Arizona, New Mexico, Texas, and California.

At Vacasa by Casago, Gregory professionally manages a portfolio of 260 short-term vacation rental properties across 12 cities in metro Phoenix, consistently achieving bonus-level performance in Net Promoter Scores and property condition standards. As General Manager of Wyndham Taos, he earned back-to-back Cornerstone Winner of the Year honors in 2018 and 2019, placing in the top third of all Tier One resorts — while also managing a $480K resort remodel and overseeing a dual-property operation.

Gregory's track record speaks for itself: a 97% annual inspection rating at Sleep Inn & Suites Austin, a Platinum Choice Hotels rating placing him in the top 3% of 1,600 properties, and a landmark contract with a Major League Baseball team that drove 40% of annual occupancy at Comfort Inn & Suites Surprise. Earlier in his career, he directed guest services for the 1,600-room Anaheim Hilton and Towers and managed call center operations supporting 7 Starwood properties and 8,000 members.

As a mystery shopping evaluator, Gregory brings an operator's eye to every engagement — identifying the gaps between brand promise and guest reality with the precision that only comes from decades of running properties at the highest level.