Supervisor, Hospitality Operations

About the Company

As the leading end-to-end investment platform for single-family rental homes (SFR), our mission is to reinvent the rental housing ecosystem for the benefit of all. We merge our passion for helping investors build wealth through real estate with cutting-edge technology that transforms the way they do it.

With a talented team of 750+ employees, our collaborative, can-do culture fuels our growth. In 2022, we closed our Series E, raising $240 million, and have offices in the Bay Area and New York City. Our growth includes acquisitions of Stessa (financial and asset management software), RentPrep (tenant screening and placement service for landlords), and Mynd (property management platform for both retail and institutional investors). In 2025, Roofstock took an ownership stake in Casago (short-term rental management services), expanding our platform to support both long-term and short-term rental investment services.

About the Team

Roofstock’s Short-Term Rental (STR) team is building and shaping an entirely new business unit. The team is obsessed with people—our owners, guests, and teammates. We extend hospitality to everyone, embrace a "no such thing as 'not my job'" mentality, and celebrate wins together. The environment is fast-paced, intense, and exhilarating, much like a startup. When the team wins, we all win.

Responsibilities

• Ensure homes under your stewardship are consistently functional, clean, and stocked (FCS) and guest-ready.
• Directly manage a team of housekeepers, overseeing day-to-day operations including scheduling, task assignment, performance monitoring, and providing ongoing coaching and feedback.
• Prioritize and delegate tasks, determining which responsibilities to handle directly and which to dispatch to Hospitality Coordinators (e.g., inspections, restocks, and other hospitality touches across the zone).
• Collaborate with Hospitality Coordinators and other Hospitality Operations Managers in your zone to support a team-first mentality.
• Maintain property-level expertise by visiting homes regularly and anticipating guest or owner issues.
• Act as the operational point of contact for assigned homeowners, ensuring responsiveness and support.
• Coordinate with central Guest Experience and Maintenance teams to resolve guest-reported issues.
• Take ownership of guest and owner issues by independently approving solutions, such as guest compensation and cost-sharing arrangements with owners as needed.
• Identify opportunities to elevate the guest experience through personalization, speed, and detail.
• Monitor guest review scores and collaborate with your team lead to raise performance where needed.
• Support inventory accuracy, issue prevention, and general property care across your assigned homes.
• Partner cross-functionally with onboarding, revenue, and field teams to ensure alignment.
• Serve as a thought partner to the Team Lead, actively contributing to the design, adaptation, and updating of process flows to better suit operational needs.
• Support training of new team members as needed.
• Provide cross-coverage in other zones as needed.
• Perform other duties as assigned.

Requirements

• 3–5 years of operational experience in hospitality, property management, or a related field.
• Strong communication and organizational skills.
• Experience coordinating or delivering fieldwork in a fast-paced setting.
• Proven ability to solve problems and act with urgency.
• Tech-savvy and comfortable using mobile and desktop task tools.
• Valid driver’s license and reliable transportation required.
• Frequent travel within market required.
• Availability to frequently work weekends, holidays, early mornings, and evenings (with 2 days off each week).
• Must be authorized to work in the U.S. (we are unable to sponsor H1-B Visas at this time).

Work Environment & Physical Demands

• Frequent travel within your assigned market.
• Availability to work weekends, holidays, early mornings, and evenings (with 2 days off each week).

Pay

Our compensation reflects several US geographic markets. The base pay for this position represents the expected salary range, but the final pay will be based on location, job-related knowledge, skills, experience, and other factors. Roofstock is a total compensation company; base salary is only part of the package.

Benefits

• Generous PTO policy.
• 12 paid holidays.
• Volunteer Time Off.
• Paid parental leave.
• 401k program.
• Wellness and home office/cell phone subsidies.
• Robust health, dental, and vision insurance.