Executive Assistant to our (Airbnb / Vrbo) Ops Manager

EXECUTIVE ASSISTANT TO OUR OPERATIONS MANAGER - Getaway and Stay, a vacation rental management business

Hi there. Please read the whole posting before you apply. The application link is at the bottom.

OVERVIEW

We manage about 50 vacation rental properties across multiple US vacation markets.. We are a growing company. Our team includes 5 amazing Online Filipino Specialists.

Becky is state-side and is our Operations Manager. She brings every new property onto management, and she works our new owner leads. Right now she does both by herself. Every new home has dozens of small items: an info sheet, a W-9, door codes, a photographer, a cleaner, supplies. Each one needs a message, a reply and a follow-up. When Becky is chasing those, she is not talking to new owners.

We are hiring one person to take that off her plate and make sure nothing she starts gets dropped. None of this is in a silo. You will work directly with both Becky as well as our amazing Filipino Ops Team. We have "all team" during your Monday evening timeframe. The Filipino Ops Team also has their own meeting later in the week,. That is where they discuss problems and complain about me, the owner. That last part was a joke.

THE SHIFT

Monday through Friday, 8am to 5pm US Central time. That is roughly 9pm to 6am Manila time, shifting by an hour when the US changes clocks. You would work the same hours Becky does, so you can hand things back and forth all day.

WHAT YOU WOULD DO

Your first job is onboarding new properties. You own the checklist from the day an owner signs until the home is live.

1. Collect. Send the owner our property info sheet and document requests. Follow up until every item is in. No reply in 48 hours gets a second message.

2. Enter. Put every detail into OwnerRez and our onboarding tracker. Door codes, wifi passwords, trash day, the hot tub brand. One wrong number in our system becomes a guest problem at 10pm. We need someone who gets it right the first time and checks it anyway.

3. Book. Schedule the photographer and the first cleaning. Track keys and lockboxes. Order supplies, ship them to the cleaner and confirm they arrived.

4. Update. Post progress in each owner's Slack channel so Becky and the owner always know where things stand.

As you learn the business, you will take on more of Becky's work. Design refresh projects, where you price Amazon lists and track deliveries. Then our owner leads. Calling and texting new leads, following up with the ones who went quiet and getting them on Becky's calendar. Later, past guest email campaigns and outreach to owners who manage their own rentals. If you have sales experience, this is where it grows.

I also do some pretty deep work in Claude, and I will teach you to use AI on this job.

WHAT YOU WOULD NOT DO

You are not walking owners through onboarding. Becky stays their main contact. You are the person who makes sure every item gets sent, collected and filed.

You are not a cold caller on day one. You will be on the phone, with owners, leads, cleaners and guests. The sales side grows over time.

WHO WE ARE LOOKING FOR

Organization and attention to detail come first. More than experience. More than your resume. The application below is built to test it, and we read every answer.

Sales is a close second. If you have set appointments, followed up on leads or worked in real estate sales, tell us. People who are great with details and great on the phone are rare. If that is you, we want to talk to you.

Beyond that:

You keep a system for open tasks, and nothing falls through it.

You write clearly. An owner should read your message once and know what to send back.

You are comfortable on the phone with Americans. Our owners need to understand you on the first try. A light accent is fine. If yours is heavier, you are willing to work on it with our training.

You follow through without being asked twice.

You are honest about mistakes.

You can work for us and only for us. No side jobs.

You have reliable internet and a backup plan for when it goes down.

TOOLS

OwnerRez, Slack, Quo, Google Drive, Google Sheets and our onboarding tracker. We will train you on all of it. You do not need to know any of them today.

PAY AND THE RAISE PATH

Starting: $3.50 - $5 per hour. This is 40 hours per week. We will have a clearly described path to raises based on specific metrics and your ability to handle the job.

We also pay 13th month before December 24. We have a medical reimbursement system. We think about ideas like "Family First."

WHAT THE FIRST 90 DAYS LOOK LIKE

Week 1-3: Daily calls with Becky and our team. You shadow, you learn our onboarding checklist and you learn our systems.

Week 4-6: You run onboarding on new properties. Becky checks your work before anything goes to an owner.

Week 7-8: You run onboarding on your own. You start writing down how to do the things you learn.

Week 9-12: You start on design projects and owner lead follow-up. Formal 90 day review.

WHY WORK HERE

We are a small team and we are going to be around for a long time. Several of our Online Filipino Specialists have been with us for several years. This role lets Becky spend her time with owners and new leads, which is how we grow. We have been doing this since 2020, and when the Google Form asks for a "number," the number is 2511. Read that last sentence again and write it down for later. We move fast and we expect you to think.

We discuss ideas like "Fix the Process, Not the Person" and "Extreme Ownership." When something breaks, we fix the system and do not blame the person. I want to empower you to make the call and not question yourself.

We will ask for a brief intro video. "Tell us about a time you kept a project on track when other people dropped the ball. Unlisted YouTube or Loom, please."

HOW TO APPLY

Fill out the application form here:

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It is mostly open-ended questions and short scenarios, and there are no trick answers. We want to see how you think and how you write.

Do not send a resume by email instead. Applications that skip the form do not get read.

Thanks for reading all the way down. We are looking forward to meeting you.

Tom Ackley
Getaway and Stay LLC