Guest Service Supervisor

Red Cottage is the premier vacation rental management company in the Northeast, with a growing portfolio of exceptional homes across Vermont, Upstate New York, Connecticut, Pensilvania and surrounding markets. We partner closely with homeowners to manage their assets, elevate guest experiences, and drive strong financial performance.

Our team blends high service standards with modern systems and data-driven operations to deliver consistent, high-quality results.

If you’re excited to help scale a premium hospitality company and play a meaningful role in shaping the future of vacation rentals in the Northeast, you may be fit at Red Cottage.

Red Cottage is seeking a Guest Service Supervisor to lead our remote front desk operations and elevate the guest experience across our vacation rental portfolio. In this role, you’ll guide a dedicated team of Guest Service Agents through the daily rhythm of arrivals, departures, and reservation management while serving as a trusted problem-solver when challenges arise. As a natural collaborator, you’ll thrive in building strong relationships across our Housekeeping, Maintenance, Portfolio Management, Sales, and Accounting teams to ensure seamless operations.

You’ll combine your hospitality expertise with a coaching mindset to develop your team, resolve guest concerns with empathy and efficiency, and help shape the processes that keep our service standards high as we continue to grow.

Own the day-to-day operation of Red Cottage's remote "front desk," leading the Guest Service team through daily arrivals, departures and reservation requests.

Support and coach a team of Guest Service Agents, including performance management and day-to-day guidance.

Serve as a primary escalation point for guest issues, taking ownership of de-escalation and guest experience recovery white on shift.

Support the team with inbound and outbound calls, emails, and chats related to reservations, service issues and general inquiries.

Assist with creating, assigning, and tracking maintenance and housekeeping tickets related to guest resolutions, ensuring timely follow-up.

Meet and maintain company performance standards and metrics, including guest satisfaction, timeliness of communication and reservation conversion.

Monitor and track individual and team performance metrics; provide coaching and feedback as needed.

Identify operational gaps and process improvement opportunities to drive efficiency and service quality.

Build strong working relationships and open communication with internal teams (Housekeeping, Maintenance, Portfolio Management, Sales, and Accounting).

Other duties as assigned—hospitality is dynamic, and flexibility is part of the role.

2+ years of experience in customer service or administrative support, preferably in hospitality, vacation rentals, property management, or a service-driven industry.

Prior supervisory or team-lead experience in a similar environment preferred.

Strong time management skills and the ability to adapt quickly in a high-volume, interruption-driven setting.

Tech-savvy, with experience using digital systems and applications; comfortable working across multiple software platforms.

Clear, thoughtful communicator who is comfortable engaging with guests, homeowners, vendors, and internal teams.

Dependable, self-motivated, and able to work independently while contributing positively to a collaborative team environment.

Flexible availability, including early mornings, evenings, weekends, and holidays, based on guest and homeowner needs.

Hourly, $18 - $20

Paid time off such as PTO, sick days, and vacation days

Health insurance

Vision insurance

Retirement benefits or accounts

Note to Applicant: This is a hybrid role, and we are accepting applications for those in the Hudson Valley and Catskills area of New York currently.