GUEST COMMUNICATION & AI OPERATIONS ASSOCIATE

ABOUT OODA

OODA Management is a San Diego-based short-term rental property management company building the next generation of how short-term rentals are run.

Short-term rental management is hard to scale. Every property is different, every guest is different, and every situation requires judgment. Most companies either deliver great personalized service at small scale, or they grow and the service quality quietly falls apart.

We are building the company that does not make that trade.

We are small and AI-native by design. We use AI tools, automation, and tight operating systems to deliver service at a level legacy property managers cannot match without hiring far more people.

Guest communication is one of the most important parts of that system.

This role starts with guest messaging, but the long-term opportunity is helping us build the guest communication engine of an AI-native property management company.

ABOUT THE ROLE

This is a guest communication role with an AI operations growth path.

Your first responsibility is simple and important: make sure guests receive fast, clear, calm, professional support.

You will respond to guest messages, follow SOPs, escalate issues, update internal systems, and help ensure guests feel taken care of during their stay.

But this is not just a message-answering job.

At OODA, every guest message is also a signal.

A guest asks a confusing check-in question. Why was it confusing?
A guest reports an issue late at night. What information do we need?
A guest asks the same thing five other guests asked. Should we update the template?
A situation keeps repeating. Should AI handle it next time?
A message could have been prevented. What was missing from the instructions?

We are looking for someone who can handle the guest professionally today, then help us make the system better tomorrow.

You do not need to be a programmer.

You do not need to have a deep technical background.

But you should be comfortable with software, interested in AI tools, and excited to learn how automation can improve operations.

WHY THIS ROLE MATTERS

Most guest messaging jobs are simple: answer questions, follow scripts, close tickets.

This is different.

OODA is building a system where human judgment and AI work together. Guest communication is one of the main places where that happens.

The person in this role will help us understand:

What guests ask most often
Which messages require human judgment
Which messages can eventually be automated
Where our instructions are confusing
Where our SOPs need improvement
Where AI responses are helpful
Where AI responses need correction
What information the team needs to make better decisions

This role is for someone who wants to become excellent at guest communication and then help us build a smarter system around it.

The starting point is guest support.

The growth path is ownership.

WHAT YOU WILL DO

Your work may include:

Responding to guest messages across Airbnb, property management tools, email, SMS, and other channels
Answering questions about check-in, checkout, WiFi, parking, amenities, house rules, and property details
Helping guests with access issues, unclear instructions, maintenance concerns, cleaning issues, and other stay-related problems
Following SOPs and message templates while still sounding natural and human
Keeping every conversation calm, clear, and professional
Updating internal systems so the team knows what is happening
Escalating maintenance, cleaning, access, or guest experience issues correctly
Tracking repeated guest questions and recurring problems
Helping improve message templates, SOPs, and internal notes
Using AI tools like ChatGPT to draft, summarize, classify, and improve communication
Reviewing AI-generated messages for accuracy, tone, and guest experience
Helping identify which guest questions can be safely automated
Helping train and refine AI-assisted guest communication over time

You will not be expected to build software.

But you should be excited to work inside a company where the goal is to make the system better every week.

THE BIGGER OPPORTUNITY

This role starts at 10 to 25 hours per week.

We are starting part-time intentionally. The first phase is about learning our properties, tools, guest standards, SOPs, and escalation rules.

For the right person, this can become full-time after the initial period.

As OODA grows, the guest communication function will need people who can own more responsibility. That may mean expanded hours, team leadership, quality assurance, SOP ownership, AI training, guest messaging management, or a more specialized AI operations role.

The best people in this function will not just answer messages.

They will help define how guest communication should work.

That means:

Better guest templates
Better escalation rules
Better AI prompts
Better training examples
Better quality control
Better reporting
Better internal notes
Better workflows between guests, vendors, cleaners, and the operations team

We are looking for someone who wants to grow with the function, not just complete a shift.

WHO WE ARE LOOKING FOR

We are looking for someone who is:

COMMUNICATION
Excellent in written English
Strong spoken English preferred
Clear, calm, warm, and professional
Able to write naturally, not robotically
Able to communicate with guests who are tired, confused, frustrated, or in a hurry
Able to follow templates without sounding like a script
TEMPERAMENT
Calm under pressure
Reliable during the agreed schedule
Detail-oriented
Patient with guests
Comfortable handling multiple conversations at once
Able to work independently during overnight coverage
Hungry for more responsibility over time
JUDGMENT
Knows when to solve and when to escalate
Does not overpromise
Does not ignore details
Can follow SOPs carefully
Notices patterns in repeated guest issues
Thinks in root causes, not just one-off replies
Can be trusted with guest-facing communication
SYSTEMS AND AI
Comfortable learning new software tools
Comfortable using ChatGPT or willing to learn quickly
Interested in AI, automation, systems, or process improvement
Able to review AI-generated messages and d ---------- whether they are accurate and appropriate
Excited by the idea of helping train AI-assisted guest communication over time

You do not need to be a developer.

But you should be the kind of person who says:

“I answered the guest correctly, but why did they need to ask this in the first place?”

That mindset matters.

THIS ROLE IS A STRONG FIT IF YOU
Have experience in guest messaging, customer support, hospitality, virtual assistance, or operations
Have supported U.S.-based customers or guests before
Can write excellent English without sounding robotic
Are comfortable working U.S. Pacific Time hours
Can handle multiple chats or messages at once
Stay calm when guests are upset or confused
Like improving templates, SOPs, and processes
Are interested in AI tools and automation
Want to grow into a larger role over time
Are based in the Philippines and comfortable working remotely

Bonus points if you have experience with:

Airbnb
Hospitable
Guesty
OwnerRez
Hostaway
Slack
ClickUp
Notion
Google Sheets
ChatGPT or other AI tools
Short-term rental operations
Customer support QA
SOP creation
Process improvement
Guest messaging management
Night shift or overnight support
THIS ROLE IS NOT FOR YOU IF

Please do not apply if:

Your written English is weak
You only want a basic VA task list
You dislike following processes
You get flustered when guests are upset
You do not want to learn new tools
You are not interested in AI, systems, or process improvement
You want a role where you only do what you are told and never think critically
You cannot work reliably during the agreed schedule
You are uncomfortable being measured on quality, reliability, and improvement

We are not looking for someone who just “handles messages.”

We are looking for someone who wants to master guest communication and help us build a better operating system around it.

THE QUALITY BAR

Because written English is the core of this job, here is the standard.

You should be able to write messages like these naturally:

“Hi Sarah, thanks for reaching out. I’m sorry about the confusion. Let me check this for you right now and I’ll follow up shortly.”

“You’re all set. The cleaner confirmed the item was found, and we’ll coordinate the best way to get it back to you.”

“I understand how frustrating that must be. I’ve escalated this to our maintenance team and will keep you updated as soon as I hear back.”

Clear. Calm. Human. Accurate.

That is the bar.

WHAT GREAT LOOKS LIKE
BY 30 DAYS
You understand our properties, tools, SOPs, and guest communication standards
You can handle routine guest messages with limited help
Your written replies are consistently clear, warm, and professional
You escalate the right issues to the right people
You are dependable during your assigned schedule
BY 90 DAYS
You can independently handle most guest messaging situations
Your judgment is reliable enough that the operations team trusts your decisions
You have identified recurring guest questions or workflow problems
You have suggested improvements to templates, SOPs, or escalation rules
You are using AI tools to improve speed and quality
BY 180 DAYS
You are not just running the workflow, you are improving it
You have helped implement concrete improvements to guest communication
You are contributing examples, feedback, and ideas that improve AI-assisted operations
You are becoming a true owner inside the guest communication function, not just a message responder
EXAMPLE OF THE MINDSET WE WANT

A normal guest messaging person says:

“The guest asked for the WiFi, so I sent the WiFi.”

A great person in this role says:

“The guest asked for the WiFi, so I sent it. But this is the fifth time guests have asked this property for WiFi this month, so maybe the check-in instructions are unclear. I recommend adding WiFi to the first arrival message.”

That is the difference.

A normal guest messaging person says:

“The guest said the door code did not work, so I escalated it.”

A great person in this role says:

“The guest said the door code did not work, so I escalated it. But I also checked whether the code was sent correctly, whether the guest was at the correct door, and whether this has happened before at this property.”

That is what we are looking for.

SCHEDULE AND GROWTH PATH

This role starts at 10 to 25 hours per week.

Coverage during U.S. Pacific Time hours is required. Overnight guest support is part of this role.

We are starting part-time intentionally. The first phase is about learning the business, proving reliability, showing strong judgment, and demonstrating that you can handle guest communication with increasing independence.

For the right person, this can become a full-time role after the initial period.

As OODA grows, we want to build long-term roles around the people who prove they can own real parts of the operation. That may mean expanded hours, full-time contractor work, a formal employment role, quality assurance ownership, team leadership, or a more specialized AI operations position.

This is not a short-term task list.

It is an entry point into the operating team of a company being built for scale.

WHEN YOU MESSAGE US

When you message us, please briefly tell us:

Your guest messaging, customer support, hospitality, VA, or operations experience
Your availability in U.S. Pacific Time
Your desired hourly rate
What tools you have used before
Whether you have used ChatGPT or other AI tools
Why this role interests you beyond basic guest messaging

Also include the word PINEAPPLE at the top of your message so we know you read the full post.