STR assistant

About the Role:

We’re looking for a highly organized, proactive, and inquisitive assistant to help run and scale a short-term rental business. The right candidate will be a problem-solver who takes initiative, communicates clearly, and thrives in a fast-paced, detail-driven environment. You’ll be expected to work independently while keeping operations smooth and guests happy.

Important note:
- This is a customer facing role for properties on EST time zone. APPLICANTS MUST BE AVAILABLE DURING BUSINESS HOURS EST
- We are hiring multiple people for this position and hours will be given based on competency and applicant availability


Key Responsibilities:

Operations & Admin

Monitor Guesty dashboard for booking updates, guest messages, and calendar changes
Oversee cleaning schedule and verify turnovers
Track maintenance issues and coordinate handyman/vendor follow-ups
Update property logs and shared documents (cleaning checklists, inventory, etc.)



Guest & Staff Coordination

Respond to escalated guest inquiries when needed (after automated messaging)
Check-in with cleaners post-turnover to verify quality and timeliness
Communicate with vendors (pest control, maintenance, laundry, etc.)
Help manage team schedules and availability

Systems & Reporting

Maintain digital checklists for cleaning and maintenance tasks
Track performance metrics (e.g., 5-star reviews, cleaner issues, maintenance costs)
Assist in monthly reporting (expenses, occupancy, issue resolution)

Required Skills & Experience:

2+ years in executive assistance, operations, or hospitality support
STR (Short-Term Rental) or property management experience strongly preferred
Excellent written and verbal communication (fluent English required)
Highly organized, with strong attention to detail
Self-starter who can solve problems without hand-holding
Tech savvy: Comfortable with Google Workspace, Guesty, TurnoverBnB, Slack, etc.
Strong judgment and ability to handle issues calmly and professionally

Tools We Use:

Guesty (PMS)
Google Workspace (Docs, Sheets, Calendar)
Slack (Team Communication)
Google Forms / Notion (Checklists & SOPs)



Schedule:

Part-time (20–30 hours/week), with flexibility to scale to full-time based on performance

9am - 10pm EST; 7 days a week

Team environment; meaning peers support one another in covering shifts and exchanging schedules


Compensation:

Competitive hourly rate
Bonus potential tied to performance and property metrics
Opportunity to grow with the business and take on more responsibility

What Success Looks Like:

Cleanings are seamless and on schedule
Maintenance is preventive, not reactive
Guest messages are handled quickly and professionally
Fewer issues get escalated to owners

How to Apply:

Please submit:

A short video (2 min max) explaining why they’re a great fit
A sample response to a mock guest issue
Resume and availability
Include interview availability over the next couple of days