Executive Assistant & STR Operations Coordinator

InsideOut; Philippines; Remote; PHP 606,000 - 692,000; Part time

Job summary

InsideOut is hiring a proactive Executive Assistant & STR Operations Coordinator to support a growing hospitality portfolio. The role covers guest communications, operations, and executive support with a 20-hour weekly schedule across remote work hours.

Strong English, 2–4 years in hospitality, and familiarity with Airbnb/Vrbo and OwnerRez are required. The position begins ASAP with training and flexible hours after onboarding, including Sunday cover and Monday prep.

Qualifications

• Direct STR/hospitality support experience (2–4 years preferred).
• Hands-on Airbnb and Vrbo experience; OwnerRez is a strong plus.
• Proficiency with AI tools and workflow automation.
• Excellent written and spoken English.
• Proactive, organized, and able to anticipate needs.

Responsibilities

• Monitor guest messaging across Airbnb, Vrbo, and OwnerRez; escalate as needed.
• Coordinate cleaners, maintenance teams, contractors, and local vendors.
• Track property issues, logs, supplies, and replenishment needs.
• Provide warm, professional guest support and responsive communication.
• Manage calendars, emails, CRM updates, and weekly prep; support market research and owner presentations.

Skills

STR/Hospitality Experience

Airbnb / Vrbo

OwnerRez

AI Tools: ChatGPT

AI Tools: Claude

English Communication

Proactive Mindset

Attention to Detail

Problem Solving

Learning Agility

Tools

ChatGPT

Claude

Automation Tools

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!

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.