Director of Operations

# Director of Operations – Short-Term Rental Property Management

**Location:** Remote
**Schedule:** Full-time | Significant overlap with U.S. Eastern Time business hours required | Weekend operational oversight required

## About the Role

We are a growing short-term rental and property management company seeking an experienced **Director of Operations** to lead the day-to-day operations of our portfolio and remote operations team.

This is a leadership position, not a traditional virtual assistant or task-based role.

We are looking for someone who can **lead people, make decisions, solve problems, build systems, manage vendors, improve processes, and ensure issues are fully resolved without requiring constant direction from ownership.**

You will oversee our Operations Supervisors and Guest Relations team while coordinating with cleaners, maintenance vendors, contractors, property owners, and company leadership.

The ideal candidate sees an operational problem, takes ownership of it, determines the root cause, gets it resolved, and creates a process to reduce the likelihood of it happening again.

## Key Responsibilities

### Team Leadership & Accountability

* Lead and support Operations Supervisors and Guest Relations team members
* Delegate responsibilities and establish clear ownership and deadlines
* Monitor team performance and operational execution
* Lead weekly operations meetings
* Coach team members and reinforce company processes and standards
* Assist with hiring, onboarding, training, performance management, and staffing decisions
* Maintain appropriate team coverage
* Step into urgent operational situations when necessary while continuing to lead at the management level

### Operational Escalations

Take ownership of escalated operational issues, including:

* Serious guest complaints
* Maintenance emergencies
* Cleaning failures
* Property access issues
* Guest relocations
* Property damage
* Utility outages
* Safety concerns
* Refund disputes
* Issues that could impact an upcoming guest stay
* Recurring problems at individual properties

You will be expected to assess urgency, determine ownership, coordinate the appropriate response, communicate with stakeholders, and follow the issue through resolution.

### Maintenance & Vendor Management

Manage relationships and work with cleaners, handymen, plumbers, electricians, HVAC technicians, contractors, locksmiths, pest-control companies, internet providers, and other vendors.

Responsibilities include:

* Requesting and reviewing quotes
* Scheduling and tracking repairs
* Evaluating vendor recommendations and costs
* Confirming completed work
* Maintaining backup vendors
* Identifying and replacing unreliable vendors
* Reviewing invoices and operational expenses
* Communicating significant expenses to leadership and property owners

You do not need to be a maintenance expert, but you should have enough operational judgment to ask the right questions before approving unnecessary expenses.

### Property Operations

Ensure recurring operational responsibilities are documented, scheduled, and completed, including:

* Preventative maintenance
* HVAC/filter replacement
* Smart locks and property access
* Lockboxes and batteries
* Deep cleaning
* Pest control
* Property supplies
* Cleaning procedures
* Backup cleaner coverage
* Property-specific recurring tasks

### Project Management & Follow-Through

We use **Asana** extensively to manage operational work.

You will be responsible for:

* Creating, assigning, and managing operational tasks
* Establishing clear deadlines and ownership
* Monitoring overdue and high-priority work
* Managing recurring workflows
* Documenting escalated issues
* Maintaining property onboarding templates
* Following up until issues are fully resolved

We place a high value on **closing loops**. Assigning a task is not the same as solving the problem.

### Systems, SOPs & Process Improvement

As the company grows, you will help build the operational infrastructure needed to scale.

This includes:

* Creating and improving SOPs
* Developing checklists and training materials
* Identifying operational gaps
* Improving inefficient workflows
* Standardizing processes across properties
* Documenting institutional knowledge
* Identifying opportunities for automation
* Building repeatable systems that reduce recurring problems

### Property Owner Communication

You will communicate directly with property owners regarding operational matters, including:

* Maintenance issues and repairs
* Property concerns
* Guest feedback
* Recommended improvements
* Significant expenses
* Outstanding operational issues
* Preparation for recurring owner meetings

Strong written and verbal communication skills are essential.

### New Property Onboarding

Help lead the operational onboarding of new properties from signed agreement through launch.

This may include:

* Collecting property and access information
* Establishing cleaners and backup cleaners
* Creating operational records and workflows
* Setting up properties within company systems
* Coordinating listing readiness
* Establishing preventative maintenance
* Documenting property-specific procedures
* Ensuring the operations team is fully prepared before launch

## Systems & Technology

Our technology stack may include:

* Guesty
* Airbnb
* VRBO
* ----------
* Asana
* Breezeway
* Happy Guest
* Ring
* Smart-lock and lockbox platforms
* Google Workspace
* Excel / Google Sheets
* Revenue-management platforms

Experience with **Guesty, Breezeway, Airbnb, VRBO, or short-term rental property management systems is strongly preferred.**

Candidates must be comfortable learning new technology quickly.

## Qualifications

**Required:**

* 3+ years of experience in operations, project management, property management, hospitality management, or a comparable leadership role
* Previous experience managing or supervising people
* Strong project and operations management skills
* Experience creating and improving SOPs and operational processes
* Experience using Asana, ClickUp, ---------- , Trello, or similar project-management software
* Strong written and spoken English
* Strong professional communication skills
* Strong Google Workspace and spreadsheet skills
* Excellent attention to detail and follow-through
* Ability to manage multiple priorities and urgent situations simultaneously
* Confidence communicating with employees, vendors, contractors, and clients
* Ability to make sound decisions without constant approval
* Comfortable working independently within a remote environment
* Reliable computer and internet access

**Strongly Preferred:**

* Short-term rental or vacation-rental management experience
* Airbnb/VRBO operations experience
* Guesty or Breezeway experience
* Hospitality operations experience
* Vendor and maintenance coordination
* Remote-team leadership
* Property-owner/client communication
* Process improvement and operational reporting

## Who Will Thrive in This Role

You will likely be successful here if you are:

* Highly organized and dependable
* Calm under pressure
* Resourceful and solutions-oriented
* Comfortable making decisions
* Assertive while remaining professional
* Strong at holding people accountable
* Naturally process-oriented
* Able to anticipate problems before they become emergencies
* Someone who follows through without needing to be reminded

Your approach to operational problems should generally be:

**Investigate → D ---------- → Delegate → Follow Up → Document → Prevent Recurrence**

## What Success Looks Like

Once fully onboarded, you should be able to:

* Run daily operations without constant involvement from company ownership
* Keep Operations and Guest Relations teams accountable
* Maintain visibility into major open operational issues
* Ensure important tasks and maintenance issues are completed on time
* Maintain a reliable network of cleaners and vendors
* Control unnecessary operational spending
* Communicate professionally with property owners
* Keep property information and systems accurate
* Identify recurring problems and create systems to eliminate them
* Successfully onboard new properties
* Continuously improve SOPs, training, and operational processes as the company grows

Ultimately, this role is not simply about managing tasks.

**Your responsibility is to make sure the operation works.**

## How to Apply

Please submit:

1. Your current resume
2. A brief description of the most complex operation or team you have managed
3. An example of an operational process you improved
4. A **2–4 minute video introduction** explaining your relevant experience, the type of team you have managed, and why you believe you are qualified for this role- please ask for an email to send the video to.

At the beginning of your application, include the phrase:

**“I CLOSE LOOPS.”**

Applications that do not follow the application instructions may not be considered.