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Stayd Collective on Hilton Head Island, SC seeks a leadership executive who owns outcomes rather than tasks. You will inherit systems and define what to formalize, reporting to the operations lead for this market and working daily with guest experience and field operations teams.
This is on-the-ground, long-term role in a strong global team with structured onboarding. You will own budgets, set standards, and address guest and partner escalations end to end, shaping how stays are managed.
Host2Coast manages vacation homes on Hilton Head Island, South Carolina. Repeat guests, long stays, and owners who often live nearby and care deeply about how their home is treated. Relationships here are measured in years, not stays.
This is a leadership seat. You own an outcome, not a task list — a market, a function or a P&L line — and you are accountable for what it does over a quarter, not what you did this week. You will inherit systems that are half-built and processes that exist mostly in somebody's head, and part of the job is deciding what to formalise and what to leave alone.
We hold ourselves to what Will Guidara calls unreasonable hospitality: doing the thing nobody asked for, that nobody would have missed, and that they will tell someone about. A guest mentions in a message that it is their daughter’s birthday, and there is something waiting on the counter when they walk in. An owner asks a question on a Sunday and gets a real answer, from a person, before Monday. We do not measure this in a survey. We measure it in whether the person on the other end felt looked after by someone who was paying attention. Everyone here is expected to notice things, and everyone here is trusted to act on what they notice without asking permission first.
You sit in Leadership and report into the operations lead for this market. This role is on the ground in Hilton Head Island, South Carolina, United States. You work every day with the guest experience team, the field operations team and the coordinators who schedule them — this is not a role where you are handed a queue and left alone. Because Stayd runs shared systems across every brand, a process you improve here tends to end up running in six other markets, which is the closest thing we have to a promotion path.
This is a long-term team role on a strong, established global team, with structured onboarding and ongoing support.
Every single applicant hears back from us, including a no. If we are not moving forward we will tell you, and we will tell you why. If you need an accommodation to complete this application, email careers@stayd.co — asking never counts against you.