Executive Operations Leader / Project Manager

Executive Operations Leader / Project Manager
Short-Term Rental Portfolio (Guesty / Airbnb / VRBO)

Location: Remote
Company Base: San Diego, California

About the Company

We are a fast-growing, systems-driven short-term rental company managing 30+ premium properties across Southern California, with plans to scale significantly.

Our portfolio includes high-end properties with complex amenities such as:

• Pools
• Hot tubs and jacuzzis
• Saunas
• Smart home systems
• Multi-level homes requiring coordinated operations

Running these properties requires excellent coordination between guest communication teams, cleaners, maintenance crews, pricing management, and operations staff.

We already have a team of capable virtual assistants handling many day-to-day tasks, but we are now seeking a high-level operations leader who can step in, organize the system, strengthen processes, and ensure nothing falls through the cracks.

This is not a typical virtual assistant role.

We are looking for someone who can take the ball by the horns and truly run the operation.

Our goal is to build a well-oiled machine where systems, processes, and team accountability allow the company to scale efficiently without constant owner involvement.

The Role

We are seeking an Executive Operations Leader / Project Manager with deep experience in short-term rental operations and Guesty PMS.

This person will help oversee the operation, improve systems, organize the team, and ensure daily operations run smoothly.

You should be someone who can quickly understand a complex operation and bring structure, efficiency, and accountability to the business.

This role may begin as a consulting or part-time leadership position (5–15 hours per week) and may expand into a larger operational leadership role depending on fit.

Our Current Tech Stack

We rely heavily on technology and systems to run the business efficiently.

Our current tools include:

• Guesty – property management system
• Slack – communication with our virtual assistant team
• WhatsApp – communication with cleaners and field teams when needed
• ---------- – operational task tracking including maintenance, lost and found, and other issues
• Google Workspace – Sheets, Docs, Drive
• Excel

We are currently evaluating additional tools including:

• Guesty Price Optimizer
• PriceLabs
• Breezeway
• Perto

The person in this role may help evaluate, implement, and optimize these systems.

Key Responsibilities

Operational Leadership

• Oversee daily operations across the short-term rental portfolio
• Identify inefficiencies and implement improvements
• Ensure operational tasks are tracked and completed
• Create structure, accountability, and clear workflows

Team Management

• Lead and organize a team of virtual assistants
• Delegate tasks effectively
• Ensure nothing falls into the operational “black hole”
• Improve communication between guest support, cleaners, and maintenance teams

Systems & Process Improvement

• Improve internal systems and standard operating procedures
• Optimize Guesty automations and workflows
• Improve task management and reporting in ----------
• Implement scalable operational processes as the business grows

Pricing & Revenue Support

• Help implement and optimize dynamic pricing tools such as PriceLabs or Guesty Price Optimizer
• Monitor calendar accuracy and pricing coordination
• Support availability management across Airbnb, VRBO, and direct bookings

Guest & Vendor Communication

• Serve as a senior escalation point for complex guest issues
• Communicate confidently with guests, vendors, and tea ---------- mbers when necessary
• Ensure high standards of guest experience across the portfolio

Reporting & Accountability

• Create operational dashboards and reporting for ownership
• Track key operational metrics
• Identify opportunities to increase efficiency and profitability

Technology & AI

• Use tools such as ChatGPT and other AI platforms to improve workflows, documentation, and operational efficiency

Required Experience

We are looking for someone who has helped run or scale a serious operation before.

You should have:

• Extensive experience with Guesty PMS
• Strong experience in short-term rental operations
• Experience managing properties listed on Airbnb and VRBO
• Experience managing remote teams and virtual assistants
• Strong operational leadership and project management ability
• Experience implementing systems, SOPs, and operational workflows
• Strong written and spoken English
• Ability to confidently communicate with guests, vendors, and tea ---------- mbers
• Strong organization and problem-solving skills

Highly Preferred Experience

• Experience with dynamic pricing tools (PriceLabs, Wheelhouse, Guesty Price Optimizer)
• Experience managing large STR portfolios
• Experience managing properties with pools, hot tubs, and complex maintenance coordination
• Experience with Slack and ----------
• Experience implementing operations software such as Breezeway or similar tools

What We’re Looking For

We are looking for someone who is:

• Highly organized
• Systems-driven
• Proactive and reliable
• A strong communicator
• Comfortable leading a team
• Able to take ownership of complex operations

Most importantly, we want someone who can step in, take responsibility, and help build a world-class short-term rental operation.

Time Commitment

Flexible.

Expected initial commitment:

5–15 hours per week

This role may expand into a larger operational leadership position depending on fit.

Compensation

Competitive and based on experience.

Opportunities for long-term growth, increased responsibility, and performance-based raises.