Director of Operations- Short Term Rentals

Position Overview

We are seeking a highly tech-savvy, experienced, and hands-on Director of Operations to fully oversee and manage the day-to-day operations of our short-term rental business. This role is designed to take over the owner’s operational responsibilities, acting as the primary decision-maker for all operational, guest experience, and team coordination matters.

This position does not handle pricing strategy or rate optimization, which is managed by a separate revenue management role. Instead, this individual will own execution, leadership, systems, SOP creation, and accountability across all properties.

The ideal candidate is a confident leader, an exceptional communicator, and a problem-solver who thrives in a fast-paced environment, enjoys technology, and is capable of independently managing multiple moving parts while improving processes over time.

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Key Responsibilities

1. Full Operational Ownership
    •    Take full responsibility for daily operations across all short-term rental properties
    •    Act as the owner’s operational representative in all day-to-day matters
    •    Make independent operational decisions that protect guest experience, property standards, and business efficiency
    •    Escalate only high-impact or exceptional issues to ownership

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2. Guest Experience & Issue Resolution
    •    Manage and oversee guest communications across all platforms with professionalism, empathy, and clarity
    •    Handle guest complaints, claims, disputes, refunds, and goodwill compensation within established guidelines
    •    Resolve issues efficiently while maintaining strong guest satisfaction and review performance
    •    Handle disputes regarding negative reviews, responding to platforms and guests appropriately
    •    Ensure prompt and effective handling of guest issues during their stay

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3. Team Leadership & Coordination
    •    Lead, manage, and hold accountable cleaning and maintenance teams
    •    Coordinate schedules, issue resolution, and follow-ups with field teams
    •    Assist with hiring, onboarding, and training operational staff
    •    Set clear expectations and maintain consistent operational standards
    •    Address team performance issues and recommend improvements as needed

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4. Property Readiness & Quality Control
    •    Ensure all properties meet cleanliness, maintenance, and readiness standards prior to guest arrival
    •    Control unit availability based on cleaning, maintenance, and operational readiness
    •    Conduct quality audits and inspections to maintain brand and service standards
    •    Identify recurring issues and implement long-term solutions

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5. SOP Ownership & Process Improvement
    •    Own the creation, documentation, implementation, and ongoing improvement of all Standard Operating Procedures (SOPs)
    •    Translate existing workflows and owner knowledge into scalable, documented processes
    •    Train teams on SOPs and ensure consistent adherence
    •    Continuously improve processes for efficiency, quality, and scalability

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6. Systems, Technology & Automation
    •    Fully manage operational tools and platforms, including:
    •    Hostaway
    •    Airbnb
    •    VRBO
    •     ----------
    •    Breezeway
    •    Slack
    •    Asana
    •    Host Buddy AI
    •    ChatGPT
    •    Leverage technology and AI tools to streamline workflows, improve guest communication, and enhance operational efficiency
    •    Identify and implement automation opportunities to reduce manual work and improve responsiveness

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7. Platform Health, Listing Optimization & Compliance
    •    Optimize property listings for maximum visibility, accuracy, and guest appeal
    •    Ensure compliance with Airbnb, VRBO, and ---------- policies
    •    Monitor platfor ---------- trics including response times, review scores, and issue trends
    •    Draft or oversee responses to guest reviews and feedback
    •    Handle disputes regarding negative reviews to protect platform reputation and maintain guest trust
    •    Protect account health and minimize operational risk

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8. Reporting & Communication with Ownership
    •    Provide regular operational reports and updates to ownership
    •    Proactively communicate risks, recurring issues, and improvement opportunities
    •    Maintain transparency and clear communication at all times

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Scope Clarification
    •    Pricing strategy and rate optimization are handled by a separate role
    •    This position will collaborate with the pricing team to ensure operational readiness but will not set or adjust pricing

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Required Qualifications
    •    Proven experience in short-term rental or hospitality operations
    •    Strong leadership and people-management skills
    •    Highly tech-savvy with advanced proficiency in operational software and AI tools
    •    Experience optimizing listings and managing platform performance
    •    Experience handling negative review disputes professionally and effectively
    •    Exceptional guest communication and conflict-resolution skills
    •    Excellent written and spoken English
    •    Ability to work independently, take ownership, and make confident decisions
    •    Strong organizational skills, attention to detail, and ability to manage multiple priorities

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Preferred Traits
    •    Calm and professional under pressure
    •    Solution-oriented and proactive
    •    Comfortable fully owning operations without daily oversight
    •    Ability to build, document, and enforce scalable processes

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What We Offer
    •    A senior leadership role with full operational ownership
    •    Opportunity to grow with an expanding short-term rental company
    •    Competitive compensation based on experience
    •    Long-term growth and advancement potential

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Important Note

This role is designed for someone ready to run operations end-to-end. If you are looking for a task-based or assistant-level role, this position is not a fit.