Executive Assistant to Operations Manager — Luxury Short-Term Rental Company (Remote, Full-Time)

Company: Helios Vacation Rentals
Location: Remote
Schedule: Full-Time, 40 hours/week — Monday to Friday, overlapping U.S. Pacific Time business hours (8:00 AM – 5:00 PM PST, hours can be discussed)
Pay: $4.50 USD/hour
Benefits: Health insurance (Maxicare Silver Plan) provided after 6 months of employment. Up to 5 days of paid time off per year.
Type: Long-term, with room to grow as the company scales

About Us

Helios Vacation Rentals is a boutique, white-glove short-term rental property management company based in the Greater Palm Springs / Coachella Valley area (Palm Springs, La Quinta, Indio). We manage a portfolio of luxury vacation homes for discerning owners and guests, backed by an in-house local team and a reputation built on Superhost status, a 4.93 rating, and 2,000+ five-star reviews.

We're growing quickly, and our Operations Manager, Marcela, needs a true right hand — someone who can become an extension of her, not just a task-taker. We're looking for a sharp, proactive Executive Assistant who wants to own this role and grow with us long-term.

This is a long-term opportunity, not a seasonal or short-term gig. All of our current virtual tea ---------- mbers have been with Helios for years, and we're looking for someone who wants to build a career with us — not just fill a temporary role. If you're looking for stability and a company that invests in its people over the long haul, this is the right place.

About the Role

This is first and foremost an Executive Assistant role. You will work directly with the Operations Manager as her second set of eyes and ears — anticipating what she needs, catching things before they become problems, and handling recurring work so she can focus on higher-level priorities.

The right person for this role does not need to ask "how do I do this?" for every task. We're looking for someone who thinks proactively, uses good judgment, figures things out, and comes to Marcela with solutions rather than just questions. Property management or short-term rental experience is a nice-to-have, but the core of this role is being an outstanding, resourceful Executive Assistant.

Key Responsibilities

Inbox & Communication Management:
Triage and manage the Operations Manager's email inbox — flag urgent items, draft responses, archive noise
Monitor and schedule guest and owner escalations as needed
Coordinate communication with our in-house team, cleaners, vendors, and contractors

Calendar & Scheduling:
Manage and protect the Operations Manager's calendar
Schedule vendor appointments, inspections, and team check-ins
Coordinate house manager and cleaning schedules around guest turnovers

Operations Support:
Track guest reservations, check-in/check-out schedules, and property turnover timelines using Hostaway
Help maintain inspection records and flag any issues that need follow-up
Maintain organized digital filing systems (contracts, owner agreements, vendor invoices, inspection reports) using Google Drive and Breezeway

Task & Project Coordination:
Track deadlines, follow up on open action items, and keep projects moving without being chased
Help build out and improve our SOPs using Notion
Support onboarding of new homes into our portfolio (setup checklists, documentation, systems entry, listing setup)
Track STR (short-term rental) permit renewal deadlines and manage the related paperwork (this is a deadline-and-document-tracking task — no licensing knowledge required)

Reporting & Documentation:
Track and maintain employee timesheets
Build and maintain Excel spreadsheets for reporting and tracking
Data entry and record-keeping across our property management systems

Guest & Owner Support:
Monitor guest escalations and help ensure timely follow-up and resolution
Support homeowner communication (updates, reporting, general correspondence)
Append and enrich homeowner/property owner lead lists (research and verify contact details) and help maintain leads in our CRM (GoHighLevel)

General Support:
Research tasks (vendors, local service providers, etc.) as needed
Ad hoc support for Marcela and the founder as priorities shift

Working with AI:
Use AI tools, specifically Claude, as part of your daily workflow — for drafting communications, research, organizing information, and streamlining recurring tasks

Who You Are:

2+ years of experience as an Executive Assistant or vacation rental property management (general VA experience alone is not enough — we need someone who has genuinely operated as a right hand to an executive or manager before or who has extensive experience with short term rentals)
A proactive, ownership-driven mindset — you take a task, figure out how to solve it, and only loop in Marcela when you genuinely need her input, not for every step. Your role is to be an extension of the Operations Manager
Strong judgment and the ability to anticipate needs before being asked
Excellent written and spoken English communication skills.
Comfortable managing multiple priorities and moving parts without dropping the ball
Proficient in Google Workspace (Gmail, Calendar, Docs, Sheets, Drive) and comfortable in Excel
Comfortable learning new tools quickly (we use Notion, Slack, and various property management systems)
Reliable, high-speed internet and a dependable computer setup

Bonus (not required, but a plus):
Prior experience in property management or short-term rental/hospitality
Experience with Notion (building or improving SOPs) and Slack
Experience with employee timesheet tracking
Experience with GoHighLevel (GHL)
Experience appending or enriching homeowner/property owner lead lists (finding contact info, verifying details, etc.)

Compensation & Benefits:
Pay: $4.50/hour, 40 hours/week
Health Insurance: Maxicare Silver Plan provided after 6 months of continuous employment
Schedule: Full-time, Monday–Friday, overlapping Pacific Time business hours
Long-term role with growth potential as Helios expands into new markets and larger properties

How to Apply

To help us see that you've read this post carefully, please include the following in your application:

Resume
A short paragraph on why this role interests you specifically — not why you'd be a great VA in general. If you have experience with any of the tools listed in the job description this is where you put it.
Detail any experience as an executive assistant or in the property management field. Include references.
Your relevant experience with Google Workspace and any property management, hospitality, or STR tools
Confirmation that you're available for the schedule listed above and can commit to a long-term, full-time position
A short (30-second) video introduction of yourself, recorded live on your computer (not a text-to-speech or edited video) — no need for anything fancy. This helps us assess both your spoken English comprehension and the stability of your internet connection, so please record it in one take without editing. Please upload it to Google Drive and share the link in your application.

Please send requested information to ---------- and CC ---------- will not respond to any applicants that do not apply in this format.

We review every application personally and look forward to meeting our next great tea ---------- mber.