Joshua Jamison

About Joshua Jamison

I build reservations teams that sell, serve, and perform at the highest level of hospitality.With over 15 years in luxury hospitality across hotel operations, guest experience, and reservations leadership, I have built my career on one core belief: that a well-run reservations function is not a call center. It is a revenue engine, a brand touchpoint, and the first chapter of every guest experience.Currently serving as Director of Reservations at Villatel, I oversee a 19-person team and a portfolio of 679 luxury vacation rental units spanning Orlando and Melbourne Beach, Florida. My team books over $10 million in annual revenue across a property mix that ranges from Marriott Bonvoy-affiliated condos to 12-bedroom private estate homes. I work closely with Revenue Management, Sales, Operations, and Guest Experience to ensure that what we do in reservations connects directly to how the guest feels from the moment they arrive.My background spans Hyatt Hotels and Resorts, Timbers Resorts, and Loews Hotels with hands-on leadership experience across Front Office, Housekeeping, Guest Experience, and Reservations. That cross-functional foundation is what separates how I think from someone who has only ever owned one department.I am a process builder, a coach, and a commercial thinker. I lead with structure, develop teams through accountability and genuine investment, and approach every operational challenge the same way: find the friction, fix the process, and build something that holds.At this point in my career, I am focused on stepping into a broader operational leadership role where reservations excellence is one part of a larger story, and where the opportunity exists to contribute at the property level across the full guest journey.If you are building a leadership team in luxury hospitality and are looking for someone who brings both the the commercial mindset and the hands-on leadership presence to make an impact from day one, I would welcome the conversation.

Experience

1. Director of Reservations

   Villatel

   Mar 2025 — Present · Orlando, FL, US

   Director of Reservations for one of Florida\'s most distinctive luxury vacation rental portfolios, spanning 679 units across private villa communities and resort properties in Orlando and Melbourne Beach. The portfolio ranges from 4-bedroom townhomes and Marriott Bonvoy-affiliated condos to 12-bedroom single-family estate homes, with individual bookings regularly exceeding per stay.Lead a 19-person reservations organization including two Reservations Managers, two Reservations Leads, five in-house agents, and a remote channel team. Responsible for all aspects of reservations strategy, lead management, conversion performance, revenue collaboration, and team development across a portfolio generating $10M+ in annual booked revenue.Drive cross-functional alignment across Revenue Management, Sales, Operations, and Guest Experience to optimize the full guest booking journey. Champion SOP development, reporting infrastructure, and OPERA PMS implementation, including a lead role in the systems and reservations buildout for a new Marriott Bonvoy property launch. Manage complex group and holiday programs including Passover, Sukkot, Christmas, and Spring Break, coordinating high-value multi-unit bookings for family groups, sports organizations, and corporate clients.Focused on building a commercially-minded reservations function that connects operational execution with revenue strategy, and on developing a team that sells, serves, and scales.