Founding Operations Associate — Short-Term Rental (Growth path to managerial/leadership role)

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TYPE OF WORK

Full Time

SALARY

$1000 - $1200/month

HOURS PER WEEK

40

DATE UPDATED

Aug 28, 2026

JOB OVERVIEW

Founding Operations Associate — Short-Term Rental (Growth path to managerial/leadership role)

Location: Remote
Type: Full-time
Compensation: $1000 to $1200 per Month / 40 hours per week — starting out at $1000 per month, increasing to $1200 per month at the end of your 90-day probation period, subject to meeting KPIs and additional work scope.
Employment: The initial employment term will be temporary for the first 90 days*.

Our Listings:

---------- /h/lazyrealm
---------- /h/lazytiny
---------- /h/mountainsandmoon

About Us

Hi there, future colleague! My name is Daniel, I’m a design enthusiast and the founder of Wildara Vacation Rentals. We were founded in 2024 and currently own and manage a small portfolio of premium short-term rental properties in California, with an active pipeline (mid to late 2027) to launch a boutique glamping resort development in Texas — 10 to 14 design-forward tiny home cabins with private wellness amenities and an event venue component. Our mission is to create beautifully designed, one-of-a-kind experiences that guests will remember and cherish.

We're hiring a Founding Operations Associate who shares our same passion for hospitality — someone who takes ownership and catches the small things before they become guest issues, is comfortable building process out of ambiguity rather than waiting for a script, genuinely appreciates the design and experience details that set us apart, and has the patience to grow with us for the long haul rather than chase a quick win. Above all, you care as much as we do about giving every guest an experience worth remembering.

You will own day-to-day guest communications, vendor coordination, and property operations across our current portfolio. This is not a static task-execution role — it's the ground floor of a long-term career and a rare opportunity to become a key member of a successful organization. You will be building out SOPs and laying the foundation for our future team expansion. As the Texas glamping properties come online, this position is designed to grow into a managerial/leadership role as our business scales.

What We Use

We value your time, that’s why we use HostBuddy AI to help automate routine, repeatable guest messaging, so you won't be handling every message manually — your focus will be on coordination, judgment calls, exceptions, and keeping operations running smoothly, not answering the same FAQ fifty times a day.

Some of the software/services we currently use to automate and manage our operations:

HostBuddy AI
Hospitable
Breezeway
Pricelabs
Truvi / Superhog
RankBreeze

What You'll Own (Including but not limited to)

Daily

Review HostBuddy conversation history and resolve any open guest tasks
Assign and follow up on cleaner tasks in Breezeway
Track deliveries and notify service providers as needed
Review cleaning results in Breezeway — check for staging, stains/damages, supply levels, propane levels, trash levels, and deliveries
Build and manage a running to-do list: maintenance items, restocking requests, last-minute or early/late check-in-outs, cleaner follow-ups on linens or lost & found
Confirm all doors are locked, adjust thermostats per seasonal settings, and check that lights/cameras (Wyze) are online, resetting light timers as needed

Weekly

Monitor pricing and occupancy; flag issues or anomalies
Maintain and update listing details as needed

Quarterly

Coordinate routine maintenance inspections
File county TOT (transient occupancy tax) reports

Annual

Run full inventory checks (dishware, linens, towels, etc.)
Schedule deep cleans and monitor results

Ongoing

Document and refine workflows and SOPs as you learn the operation
Help source, screen, and train additional team members as we scale
File damage/insurance claims when needed
Support basic bookkeeping tasks
Upsell early check-in / late check-out and other service packages

What We're Looking For

Prior hands-on experience with Airbnb, Vrbo, ---------- and other STR platforms — you understand guest expectations and how a well-run property operates, not just customer service in the abstract
Excellent verbal and written communication as well as a professional demeanor for guest and vendor interactions
Extremely organized and detail-oriented — you'll be tracking multiple properties, vendors, and recurring deadlines at once, and building systems and processes to streamline operations
Self-motivated and comfortable driving initiatives independently — we want someone who builds and improves processes, not just follows a script
Comfortable handling maintenance coordination and knowing when an issue needs escalation vs. a standard fix
Tech-savvy — Has expertise in Google Suite, willing to learn new software and platforms as necessary, and using AI to improve operational efficiency
Growth-minded — genuinely interested in taking on more ownership as the business expands, not just looking for a fixed-scope task role
Access to stable high-speed internet (speedtest link required; https://www.speedtest.net)
Must have your own computer, backup power, and internet connection in case of power interruptions
Flexibility with working hours, including evenings and weekends as needed
Must not have other employment as we require your full dedication. A quiet work environment is necessary

Required Days/Hours:

Monday to Friday: 9:00 AM - 6:00 PM PST (1 hour unpaid Lunch Break)
*Please note that the US observes daylight savings time.

Growth Path

This role is structured to grow in three stages:
Customer Service and Operations Associate: Own day-to-day communications, vendor coordination, and property upkeep across the current portfolio.
Operations Manager (as Texas glamping launches): Take on multi-site coordination, vendor relationships in a new market, and build out our team with additional hires and systems.
Leadership Role (as the business scales): Oversee managers and systems across multiple sites as we grow.

Promotion and compensation increases are tied to demonstrated ownership at each stage, not tenure alone.

How to Apply

If you are interested in this position, please send an application with the EXACT subject line “I’m your next Experienced and Dedicated Founding Operations Associate” and include the following:
-Your resume/CV
-Your speedtest.net link for internet speed verification
-Complete our skill assessment here: ----------
-Showcase your qualifications and enthusiasm by attaching a short video recording (using whichever recorder you prefer - can be a recording from your phone) explaining the following:
1. Brief introduction of yourself and your experience (What STR platforms or property management systems have you used (Airbnb, Vrbo, Hospitable, etc., and what did your day-to-day work look like)?
2. Tell me about a specific time you turned around a guest's bad experience into a great one. What happened, what did you do, and how did it feel afterward?
3. Tell me about a time you noticed a recurring problem at a job and built a process, checklist, or fix for it without being asked.
4. This role starts with guest communications and operations but is designed to grow into a leadership role as we scale into Texas. What does a growth path like that mean to you, and how do you think about the timeline for taking on more responsibility?

SKILL REQUIREMENT
Project Management Sop Writing Short Term Rentals
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