Executive Assistant & STR Operations Coordinator

InsideOut; Philippines; Remote; PHP 608,000 - 694,000; Part time

Job summary

InsideOut seeks a proactive Executive Assistant & STR Operations Coordinator to support a founder-led hospitality and vacation rental portfolio. This remote, part-time role blends executive support with STR operations, guest communications, and workflow optimization.

Ideal candidates have 2–4 years in hospitality or virtual assistance, are fluent in English, tech-savvy, and comfortable using AI tools to boost efficiency. 20 hours/week with ASAP start.

Qualifications

• Direct STR/hospitality experience with 2–4 years.
• Hands-on Airbnb and/or Vrbo experience; OwnerRez is a strong plus.
• AI tools like ChatGPT/Claude and workflow automation experience.
• Excellent written and spoken English; proactive communicator.

Responsibilities

• Manage guest messaging across Airbnb, Vrbo, and OwnerRez.
• Coordinate cleaners, maintenance teams, contractors, and vendors.
• Manage inboxes, calendars, CRM, files, and follow-ups; weekly Monday Reset.
• Create and optimize SOPs and recurring workflows; assist with market research.
• Publish social media content and assist with guest marketing; maintain records.

Skills

STR/Hospitality Experience

Airbnb/Vrbo

AI tools / Workflow automation

Communication

Proactive mindset

Attention to detail

Problem solving

Judgment

Learning agility

Tools

OwnerRez

Job description

Exciting Remote Opportunity! We're Hiring an Executive Assistant & STR Operations Coordinator!

Are you a proactive, hyper-organized, and tech-forward hospitality professional? We are looking for an exceptional Executive Assistant & STR Operations Coordinator to support a growing, founder-led hospitality and vacation rental company!

IMPORTANT - Watch this quick Loom video on how to get hired: https://www.loom.com/share/345f776084e642ba99c24aabe40a67a0

C1 ENGLISH LEVEL IS REQUIRED.

The selected candidate will be speaking strictly in English during their whole shift.

Job Details at a Glance

• Job Title: Executive Assistant & STR Operations Coordinator
• Job ID: JULKYL1
• Industry: Hospitality Management
• Location: PH (Philippines)
• Job Status: Part-Time (20 hrs/week)
• Work Schedule:
• First 90 days: Strategic overlap Monday–Friday, 10:00 AM–6:00 PM ET for training and shadowing. Exact hours will be agreed upon with the selected candidate.
• After 90 days: Flexible 20 hrs/week, ideally including Sunday checkout coverage, Monday morning preparation, and evening overlap Thursday–Saturday.
• Salary: $7–$8 per hour
• Target Start Date: ASAP

About the Client

The client is a growing, founder-led hospitality company managing an established vacation rental portfolio while expanding into hospitality, real estate, and coaching initiatives. The company focuses on intentional care, seamless service, and thoughtful guest experiences.

About the Role

We are seeking a proactive, hyper-organized, and tech-forward Executive Assistant & STR Operations Coordinator with 2–4 years of hospitality or virtual assistant experience. You will support short-term rental operations, executive administration, guest communication, and business workflows while helping the founder streamline operations and grow the business.

PLEASE NOTE:

This is a proactive, high-ownership role. The ideal candidate should have direct short-term rental/hospitality experience and be able to anticipate needs rather than wait for instructions.

1. STR & Hospitality Operations

• Monitor guest messaging and handle escalations across Airbnb, Vrbo, and OwnerRez.
• Coordinate cleaners, maintenance teams, contractors, and local vendors.
• Track property issues, logs, supplies, and replenishment needs.
• Provide warm, professional, and timely guest support.

2. Executive & Operations Support

• Manage inboxes, calendars, meeting preparation, CRM updates, files, and follow-ups.
• Execute the weekly "Monday Reset" and summarize key priorities.
• Create and improve SOPs and recurring workflows.
• Assist with market research, property data, and owner presentation decks.
• Schedule and publish social media content using provided materials.
• Assist with basic email marketing for guest retention and direct bookings.
• Maintain accurate CRM, property, and lead records.
• Use ChatGPT, Claude, and other AI tools to improve efficiency and communication.
• Learn new platforms, automations, and operational tools as the business grows.

Qualifications & Skills

• STR/Hospitality Experience: Direct experience supporting short-term rentals or hospitality operations (2-4 years preferred).
• Platform Knowledge: Hands-on Airbnb and/or Vrbo experience; OwnerRez is a strong plus.
• AI & Technology: Comfortable using ChatGPT, Claude, and workflow automation tools.
• Communication: Excellent written and spoken English.
• Proactive Mindset: Anticipates needs and takes initiative without waiting for instructions.
• Attention to Detail: Highly organized with strong follow-through.
• Problem Solving: Solution-oriented and able to provide recommendations.
• Judgment: Able to prioritize calmly in a fast-moving environment.
• Learning Agility: Adaptable, resourceful, and eager to grow into a trusted right-hand partner.

First 90-Day Trajectory

• Days 1–30 – Learn & Shadow: Learn the properties, systems, people, workflows, and priorities.
• Days 31–60 – Begin to Own: Take ownership of recurring workflows, guest escalations, Monday preparation, follow-ups, and documentation.
• Days 61–90+ – Own & Anticipate: Independently manage assigned areas, improve workflows, anticipate needs, and create operational capacity for the founder.