OPERATIONS & AI SYSTEMS ASSOCIATE:AI-NATIVE SHORT-TERM RENTAL OPERATIONS

OPERATIONS & AI SYSTEMS ASSOCIATE


Location: Remote, working U.S. Pacific Time hours
Type: Part-time contractor to start, 10 to 25 hours per week, with a clear path to full-time
Reports to: Christian Johnston, Founder
Compensation: Based on experience and competency, with structured raises at 30/90/180 days and KPI-based bonuses on top of base. Discussed in the interview.

This role starts part-time because we want to make sure there is a strong fit on both sides. For the right person, this can expand into full-time work after the initial period. As the company grows, there is also a path from contractor status into a more formal employment role, depending on performance, availability, location, and mutual fit.

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 genuinely hard to scale. Every property is different, every guest is different, every owner is different, every vendor is different, and every situation requires judgment.

Most companies hit the same wall: they 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.

This role is for someone who wants to join that operating system from the inside.

ABOUT THE ROLE

This is a general operations support role with an AI systems growth path.

You will be assigned into one of our operating divisions, such as guest communication, maintenance coordination, cleanings, owner support, reservations, vendor coordination, or internal operations.

You will start by doing the actual work.

That part matters.

You cannot improve a system you do not understand. You cannot train AI on a workflow you have never lived. You cannot build better SOPs, templates, escalation rules, or automations unless you know where the real friction is.

So the path is simple:

Learn the division
Do the work
Document the patterns
Identify what breaks repeatedly
Help improve the workflow
Help train AI and automation around the work
Grow into more ownership as the company scales

This is not a basic VA role.

We are not looking for someone who only wants to complete tasks forever. We are looking for someone who can become excellent inside an operating function, then help us make that function smarter, faster, and more scalable.

WHY THIS ROLE MATTERS

Every operating division at OODA has the same core challenge:

There are lots of small decisions happening all the time.

A guest asks a question.
A cleaner reports a problem.
A vendor texts back late.
An owner needs an update.
A maintenance issue needs triage.
A task is missing context.
A process works 80% of the time, but fails in edge cases.

Most companies solve this by hiring more people.

We are solving it by building better systems.

The person we want is not just someone who says, “I completed the task.”

The person we want says:

“Why did this task exist?”
“Why did this break?”
“What information was missing?”
“What should the SOP say?”
“What could AI handle next time?”
“What should still require a human?”
“How do we make this easier for the next person?”

That is the mindset.

You will do real operational work, but the long-term opportunity is to help build the system behind the work.

WHAT YOU WILL DO

Your exact responsibilities will depend on the division you are assigned to, but may include:

Responding to guest, owner, vendor, or tea ---------- ssages
Coordinating maintenance, cleanings, inspections, or property tasks
Updating internal task systems so the team always knows what is happening
Following SOPs, checklists, templates, and escalation rules
Identifying issues that need human judgment
Escalating problems clearly and correctly
Tracking repeated questions, bottlenecks, delays, and recurring problems
Helping improve SOPs, templates, checklists, and workflows
Using AI tools to draft, summarize, classify, organize, and improve work
Helping train AI-assisted workflows with real examples from the business
Giving feedback on what the system gets right and wrong
Helping turn messy real-world operations into cleaner repeatable processes

You do not need to be a software developer.

But you should be excited to work in a company where the goal is to use AI, automation, and operational discipline to make the business better every week.

THE BIGGER OPPORTUNITY

This role starts at 10 to 25 hours per week.

But we are not hiring for a temporary task list. We are building a team.

As OODA grows, each operating division will need people who can own more responsibility. Guest communication, maintenance, cleanings, owner support, vendor coordination, internal QA, AI training, process improvement, and operations management all become more important as we scale.

The best people in these seats will not just do the work.

They will help define how the work should be done.

That means:

Better SOPs
Better AI prompts
Better message templates
Better escalation rules
Better quality control
Better dashboards
Better reporting
Better training data
Better workflows between humans and AI

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, division ownership, team leadership, or a more specialized AI operations position.

The starting point is operations.

The growth path is ownership.

WHO WE ARE LOOKING FOR

We are looking for someone who is:

COMMUNICATION
Excellent in written English
Strong in spoken English preferred
Fluent Spanish strongly preferred
Clear, calm, and professional
Able to explain issues without drama or confusion
Able to write like a thoughtful human, not a script or translation tool
TEMPERAMENT
Calm under pressure
Reliable during the agreed schedule
Detail-oriented
Comfortable with repetitive work at first
Hungry for more responsibility over time
Not too proud to start by doing the work directly
JUDGMENT
Knows when to solve and when to escalate
Follows SOPs without becoming robotic
Notices patterns
Thinks in root causes
Can handle ambiguity without freezing
Can be trusted with real operational responsibility
SYSTEMS AND AI
Comfortable learning new software tools
Curious about AI, automation, and process improvement
Interested in helping train and improve AI-assisted workflows
Able to use tools like ChatGPT thoughtfully
Excited by the idea of doing the work first, then helping improve the system

You should be the kind of person who completes a task correctly, then asks:

“Why did this take so many steps, and how could we make it better?”

That mindset matters more than any single tool on your resume.