Property Management Team Leader

Job Summary:

We are looking for an experienced, hands-on Remote Property Manager to lead the Shared Services Team. The ideal candidate has real short-term rental (STR) property management experience and is comfortable making fast, sound decisions on guest issues, policy exceptions, and revenue matters. The Remote Property Manager acts as the first line of leadership for the Shared Services Team, ensuring guests are taken care of, partners are informed, and revenue is distributed accurately and on time.

Key Responsibilities:

Team Leadership & Knowledge Management

Lead the Shared Services Team in answering questions related to guest messages.

Ensure all guest and partner messages are sent according to the knowledge center protocol.

Keep the knowledge center updated with new information as procedures and policies evolve.

Report inconsistencies to the Shared Services Team Leads and correct incorrect procedures.

Guest & Reservation Operations

Monitor reservations and abnormalities related to in-house guest issues, resolving them directly whenever possible without the need to involve the partner.

Serve as the decision-maker for exceptions to policies and goodwill gestures.

Monitor the Slack channel and Hospitable 24/7, or ensure someone is correctly responding to escalations around the clock — including overnight hours, weekends, and holidays.

Manage housekeeping schedules and ensure tasks are handled correctly and on time.

Platform & Systems Oversight

Communicate directly with OTA platforms and Hospitable when needed, escalating and finding alternative solutions when they are unhelpful or unresponsive.

Check that all automations are running correctly, and manually verify and correct workflows when they are not.

Revenue Management

Ensure that OTA Revenue is distributed to each partner accordingly.

Prepare owner statements and send all revenue to the partners every month

Requirements:

Minimum of 3 years of experience in the short-term rental (STR) industry — hands-on, guest-facing property management experience is required, not adjacent hospitality or general customer service experience.

Demonstrated working knowledge of the types of issues guests typically raise during a stay (check-in/check-out, access, amenities, cleanliness, noise, damage, cancellations, refunds, etc.) and how to resolve them appropriately

Availability and willingness to work a non-traditional schedule, including being reachable for emergencies overnight, on weekends, and on holidays.

Additional Requirements:

Prior experience managing or leading a team, ideally in a remote or distributed setting.

Strong, confident decision-making skills, particularly around policy exceptions and guest goodwill gestures, balancing guest satisfaction with business impact.

Working familiarity with major OTA platforms (Airbnb, Booking.com, Vrbo/Expedia) and channel/property management systems such as Hospitable (or similar PMS tools).

Comfort working within Slack and other messaging/escalation tools for round-the-clock monitoring.

Basic financial literacy sufficient to review revenue distributions, reconcile payouts, and prepare monthly owner statements accurately.

Excellent written and verbal English communication skills, with the ability to communicate professionally with guests, partners, and OTA support teams.

Strong organizational skills to manage housekeeping schedules and coordinate across multiple moving parts simultaneously.

Ability to identify process gaps or breakdowns (e.g., automation failures, outdated procedures) and take ownership of fixing them rather than just flagging them.

Comfortable presenting updates and suggestions in meetings with cross-functional

Reliable high-speed internet connection, a dedicated remote workspace, and a backup power/internet plan given the on-call nature of the role.

High degree of integrity and transparency, given direct responsibility for partner revenue and owner reporting.

What Makes This Role a Good Fit

This position suits an experienced STR property manager who thinks like an owner — someone who already knows how to keep guests happy, knows what "normal" looks like in day-to-day operations, and can be trusted to make judgment. It is best suited to someone who wants ownership over a portfolio's operational success rather than a narrowly-scoped, shift-only support role.

Work Schedule

The successful candidate will work a minimum of 5 shifts of 8 hours per week and must be willing and able to step in outside of scheduled hours whenever operational emergencies arise — including overnights, weekends, and holidays. Candidates who are not comfortable engaging with operations outside of standard business hours will not be a fit for this position.