Short-Term Rental Specialist | Executive Assistant

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TYPE OF WORK

Full Time

SALARY

4.0-5.0 USD Per Hour

HOURS PER WEEK

40

DATE UPDATED

Aug 29, 2026

JOB OVERVIEW

Endless Real Estate

About Us

Endless Real Estate is a growing real estate company with three business lines: Real Estate Sales (where your Executive Assistant work sits), Endless Stays (our own premium short-term rentals across NJ, TN, FL & VA), and Endless Asset Management (short-term rental management and co-hosting for other property owners). We're growing fast with an ambitious 10-year vision — this is a career opportunity, not just a job.

Our Core Values: World-Class Hospitality to Every Guest and Owner • Fix Once, Fix Forever • Own the Outcome • Systems Create Scale • Bring Excitement, Passion, and Integrity Every Day

Please read this posting carefully. Due to applicant volume, applicants who do not follow the instructions in this posting explicitly will not be considered.

The Role

We're hiring one fully remote team member to run our short-term rental operations day to day. This role will ultimately act as Executive Assistant to the Owner — responsible for all admin and ops work across our real estate business — with a clear path into leadership as we scale.

Schedule: Thursday–Monday, 9:00 AM–6:00 PM US Eastern, with a 1-hour unpaid lunch (Tuesdays and Wednesdays off).

Virtual office: You'll work camera-on in our virtual office during your shift — it's how our remote team stays connected. This one is (politely) non-negotiable.

Short-Term Rental Operations:


Own guest communication end-to-end, from inquiry through post-stay
Manage reservations across Airbnb, VRBO, ---------- , and direct
Coordinate cleaners, maintenance, and service providers
Monitor property conditions and uphold quality standards
Handle troubleshooting and service recovery
Execute company systems and keep documentation sharp


Executive Assistant & Admin:


Own admin and operations support for the Owner across all three business lines
Accounts payable and basic monthly prep for our bookkeepers
Admin support for social media and marketing
Qualifying calls with potential co-host clients


AI & Automation:


Learn and use AI tools — Claude and ChatGPT are part of the daily job here, and you'll be responsible for getting great at them
Work directly with our AI agents and workflows to make sure company systems and automations are running effectively
Review our AI guest-messaging tool and ensure every guest interaction is high-quality


Tech you'll use: Slack, Notion, Google Workspace, Claude, and ChatGPT are our core ecosystem — you'll live in them daily. Property stack: Hospitable/OwnerRez (PMS), Breezeway, Quo, HostBuddy, StayFi, RankBreeze, Go High Level. We automate the repetitive work — you run the systems, catch the exceptions, and flag what we should automate next.

Who You Are


Experienced in STR — you've actually managed short-term rentals before (required)
Service-hearted — you're looking to serve and proud to be someone's right hand, always asking "what else can I do to make their life easier?"
Collaborative — you communicate proactively and make the whole team better
Growth-driven with a passion to learn — you want a career track, not a static role; we promote from within
Extremely comfortable with technology and AI — you pick up new platforms fast and work with AI tools daily; at a minimum, you'd describe yourself as extremely efficient and productive
Detail-obsessed — avid note-taker; nothing slips through
An owner — you drive outcomes and solve problems without being chased
Positive and high-energy — you bring excitement to work every single day; it's contagious and it's essential here


Hard requirement: Fluent English at a 9/10 level — written and verbal — with college-level comprehension (non-negotiable — please don't apply otherwise).

Huge plus: Notion, OwnerRez, or Hospitable experience.

What Makes This Different

This is a startup, not a steady-state job. We're building systems and evolving constantly — if you're looking for routine, this isn't the role. You'll work directly with the CEO and get hands-on mentorship and training from day one. Your work directly drives guest satisfaction, property performance, and company growth.

Compensation


Competitive salary based on experience
Performance bonuses tied to property metrics
Fully remote
Clear advancement path with increased compensation


How to Apply

Submit:


Your resume
A 2–3 minute video introducing yourself, including a time you went above and beyond for a customer
Any questions you have about the position — including your salary requirements and whether they are negotiable


Important: To demonstrate your attention to detail, include the word "Jersey" in the subject line.

Reminder — due to applicant volume, applications that do not follow these instructions explicitly will not be considered.

If You're Selected to Interview

Due to applicant volume, candidates selected to interview will be required to watch a 25-minute video from our CEO and record answers to 6–7 questions and scenarios before a live interview.

This opportunity will be incredible for someone who is looking to grow, wants direct mentorship and training from the CEO, and really wants to be excited to come to work every day. We move fast for the right candidates — if that's you, apply now.

SKILL REQUIREMENT
Real Estate Short Term Rentals English Proficiency
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