Location & Employment Details

Location: Fully remote
Employment type: Full-time preferred; open to a part-time ramp (e.g., 20 hrs/week for the first 3 months) converting to full-time
Schedule: Substantial overlap with North American business hours (Eastern Time preferred); guest-facing responsiveness required
Reports to: Founder / Owner-Operator

About the Company

We are a growing, independently-owned hospitality and property management group. Our operations span two connected businesses: a boutique resort and event venue — offering cabins, a lodge (currently expanding), and full-property buyouts for weddings, corporate retreats, and offsites — and a midterm rental placement business that lists and fills 30+ day rentals on behalf of property owners.

We run lean and move fast. Reservations flow through CloudBeds and major OTA channels (Airbnb, Expedia, Booking.com), and we lean heavily on modern tools — including AI — to punch above our weight. This is a founder-led environment where initiative is rewarded and the right person can own real scope from day one.

About the Role

This role exists because the business has outgrown what the founder can personally manage across multiple ventures. Guest messaging across OTAs needs to be fast, warm, and consistent to protect ratings and bookings. A library of photo and video content is sitting unused because no one owns publishing it. And the midterm rental arm needs someone reliable on the phone to keep placements moving.

You will be the connective tissue across all three: the person who keeps guests informed, keeps the brand visible, and keeps rental coordination on track — so the founder can focus on growth rather than day-to-day execution. It is a hybrid of hospitality operations, marketing execution, and rental coordination, best suited to someone who likes variety and takes ownership without being told twice.

Key Responsibilities

Guest Communications & Reservations (CloudBeds)

Manage inbound and outbound guest messaging across Airbnb, Expedia, and Booking.com through CloudBeds
Respond promptly to inquiries, booking requests, and guest questions, maintaining response times that protect OTA and Superhost-level rating standards
Coordinate reservations, confirmations, and check-in / check-out logistics
Manage calendars and availability across channels to prevent double-bookings
Support special bookings — weddings, corporate retreats, and full-property buyouts — including detail-gathering and coordination
Handle guest issues professionally and escalate when appropriate

Marketing & Content

Pull from the existing content library (photos and videos) to assemble simple, on-brand social posts
Schedule and publish content to Instagram and Facebook on a consistent cadence
Write captions and light copy; perform basic engagement (comments and DMs)
Track what performs and adjust the posting plan accordingly

Midterm Rental Coordination

Support the 30+ day rental placement arm end to end
Make outbound calls to prospects, leads, and partners to move placements forward
Coordinate listings, follow up with tenants and owners, and keep records current

Operations & Admin

Provide calendar, inbox, and document support across the businesses
Use AI tools (e.g., Claude, ChatGPT) daily to draft, summarize, and speed up routine work
Identify repeatable workflows and help document them into simple, reusable processes

Required Qualifications

2+ years in a remote coordinator, virtual assistant, guest services, hospitality operations, or property management role
Excellent written and spoken English — this role messages guests and makes calls daily
Hands-on experience with a hospitality or reservation platform and OTA channels (Airbnb, Booking.com, Expedia)
Comfortable and confident making outbound phone calls
Social media management experience (Instagram, Facebook), including scheduling and basic content assembly
Demonstrated, practical AI proficiency in day-to-day work — this is a non-negotiable
Self-directed and proactive, comfortable operating in a fast-moving, founder-led environment
Reliable computer, headset, and internet, with the ability to overlap North American business hours

Preferred Qualifications

Direct experience with CloudBeds
Bilingual English / Spanish
Short-term, vacation, or midterm rental operations experience
Content creation and editing skills (Canva, CapCut, or similar)
Experience supporting events such as weddings or corporate retreats
Experience coordinating across multiple properties or brands

Ideal Candidate Profile

You are:

Highly organized and proactive — you think a step ahead instead of waiting for instructions
Warm and professional in every guest interaction, and protective of the brand's reputation
Comfortable wearing multiple hats across hospitality, marketing, and rentals
Genuinely fluent with AI tools and eager to use them to work smarter
At home with autonomy and ambiguity — you build structure where none exists yet
Calm under pressure, with follow-through you don't have to be reminded about

Why Join Us

Real ownership and variety across three connected businesses, not a narrow single-task role
A founder who values initiative and gives capable people room to run
A tech-forward, AI-first team that invests in working smarter
Growth alongside an expanding resort and rental operation

Hospitality & Property Operations Coordinator (VA) - 21600