Full Time
$600-$1000
40
Apr 9, 2026
Company: 5 Seasons Homestays
Location: Remote
Type: Full-time Virtual Assistant
Openings: 1
About Us
5 Seasons Homestays is a short-term rental property management and co-hosting company. We specialize in delivering exceptional stays through strong communication, fast resolutions, and consistent operational standards.
Role Overview
We are hiring one Guest Experience Operator to handle guest messaging, reservation support, listing updates, and issue resolution across multiple channels. This role is ideal for someone who is warm, calm under pressure, highly detail-oriented, and confident communicating at a native level.
Key Responsibilities:
Manage guest communications across platforms (inbox, SMS,
Respond quickly and professionally to inquiries, requests, and guest issues
Support reservations, stay instructions, check-in/check-out guidance, and troubleshooting
De-escalate complaints and turn negative situations into positive outcomes
Coordinate with internal operations (maintenance/cleaning) to resolve issues fast
Update listings and guest-facing instructions to reduce repeat questions/issues
Document issues, preferences, and follow-ups for team continuity
Maintain response-time standards and high guest satisfaction
Required Qualifications (Must-Have):
C2-level English proficiency (native-level speaking and writing)
Strong warm, professional, conversational communication style with empathy
Customer service mindset with excellent de-escalation and problem-solving skills
Ability to manage multiple chats/conversations at once without missing details
Reliable internet, quiet workspace, and ability to handle calls professionally
Preferred Qualifications
Hospitality / customer support / travel industry experience
Short-term rental guest communication experience (
Familiarity with SOP-based operations
What Makes 5 Seasons Homestays Different
We treat guest experience as a system, not improvisation
Clear standards, strong training, and a team that values ownership and follow-through
Growth potential into senior guest operations or team lead roles
How to Apply (Required)
1. Send your updated resume
2. Submit ONE Loom video (max 5 minutes) covering the tasks below
How to submit: Record at
TASK 1: Introduction (1 minute)
- Introduce yourself
- Share relevant experience
- Why this role at 5 Seasons Homestays?
TASK 2: Multi-Channel Communication Scenario (2 minutes)
At 2 PM you are handling:
- Phone call: guest on hold about Wi-Fi issue
- SMS: guest asking about early check-in (3 hours early)
-
Show how you prioritize, and give your word-for-word response to ONE scenario.
Important: Applications without the Loom video will not be reviewed.