Find & Apply For Operations Manager / Supervisor Jobs in Gouldsboro, Pennsylvania

Role:

Operations Manager Stay Booked is a rapidly growing luxury vacation rental management company in the Pocono Mountains and Maryland & Delaware beaches. We exist to deliver homeowners and investors with the white-glove, full-service experience that we would demand for our own investment properties. Leveraging decades of executive experience in marketing, sales and operations, we specialize in maximizing the revenue of large, one-of-a-kind vacation rental properties. We are looking for a detail-oriented, energetic, and results-driven Operations Manager to own everything that happens from the moment a guest books to the moment they leave the property - including team performance, property condition, and guest experience outcomes. You will be responsible for running and scaling the day-to-day operations of a high-end vacation rental portfolio. This is a leadership role focused on managing people, systems, and outcomes — not executing tasks. If you are someone who thrives on ownership, accountability, and building systems that scale, this role is designed for you.

Employment Type:

W-2 (hourly to start, transitioning to w2 after 3-month trial; no health insurance benefits, although that is subject to change as we grow)

Location:

Remote in Northeast or Mid-Atlantic (being located in the Poconos is a plus!)

Hours:

9am-5pm EST, Monday-Friday. Available some evenings & weekends for escalations only (not primary coverage) Flexible PTO (with proper coverage in place)

Travel:

Must be able and willing to travel to properties every 4-6 weeks for quality checks and on-boardings. Responsibilities Core Values Know and embody our Core Values - Deliver a Delightful Experience, Uphold the Standard, Practice Extreme Ownership, Correct the Process, Not the Person. Leadership Leverage "Who Not How" to direct all personnel responsible for day-to-day operations, including in-house Guest Experience (GX) team, external cleaning and maintenance companies, and specialty contractors. Hire, manage, train, grow and inspire our offshore Guest Experience team (located in Philippines) to meet and exceed company standards in delivering a 5-star guest experience. Oversee, hire, manage, train and grow our locally-based cleaning inspectors, runners, and handymen to ensure properties are kept in top-notch condition. Embody our core values and make data driven decisions with the goal of exceeding company goals & KPIs. Guest Experience Spot-check guest messaging and issue resolutions to ensure timely and effective communication from the GX team that results in 5-star reviews. Resolve escalated guest or maintenance issues in accordance with their urgency to generate positive guest outcomes and minimize refunds. Monitor and update all listings and welcome guides for accuracy. Operations Oversee the creation and updating of our internal systems, documentation, and processes - ensuring our business is constantly growing and evolving in ways that efficiently and effectively deliver our standard of service. Ensure all routine cleaning and preventative maintenance inspections are completed on time and findings are addressed in a timely manner (immediately for cleaning; <7 days for maintenance). Own the management of our property maintenance boards, ensuring issues are identified and fixed in a timely manner (<7 days). Property Onboardings Serve as lead project manager and homeowner point of contact for all new property onboardings. Own all aspects of the onboarding process and ensure projects meet target 'Go-Live' dates. Technology and Software Management Know our tech stack inside and out and utilize the tools available to you to effectively monitor the performance of our in-house and external teams. Key software applications include Hospitable, Monday.com, Slack, Breezeway, WhatsApp, Quo, and the Google Business Suit. Stay on top of industry trends to identify & implement opportunities to simplify/improve our systems. What Success Looks Like in This Role The CEO is no longer the bottleneck for operational decisions The GX team operates independently with minimal escalation Maintenance backlog is consistently under control New property onboardings are predictable and on-time Systems are documented, repeatable, and improving Airbnb SuperHost status is maintained with a host review score of 4.96 or higher. Requirements Energetic embodiment of our Core Values. Familiarity with Airbnb, short-term rentals, or property management. Experience in high-volume operations environments Strong leadership and management skills. Excellent communication and organizational skills, with an extreme attention to detail. Ability to prioritize and manage multiple concurrent projects with deadlines A knack for hospitality and guest service - you always go the extra mile. Tech-savvy and comfortable learning new software. Compensation Hourly rate for three-month trial period, transitioning to w2 salary once trial is successfully completed. No health benefits to start, but will be provided as we grow. Annual performance bonus based on Host Review Score, maintenance SLAs and property onboarding timelines. $500 lead generation fee for qualified leads that turn into signed contracts.

Pay:

$65,000.00 - $85,000.00 per year

Benefits:

Flexible schedule Paid time off

Experience:

short-term rental: 1 year (Required)

Work Location:

Hybrid remote in Gouldsboro, PA 18424