65730672148 - Short-Term Rental Operations Specialist

Short-Term Rental Operations Specialist (Mid-Term & Corporate Housing)

Client Context: Chicago-Based Corporate Housing & Mid-Term Rental Enterprise (14 Units)

Schedule: Full-Time (40 hours/week) | US Central Standard Time (CST) Alignment

Flexible 8-hour shift between 7:00 AM – 5:00 PM CT (covering peak morning check-ins and inquiries while the founder rests).

Type: Full-Time Remote Contractor

Position Overview

We are seeking a warm, process-driven Short-Term Rental Operations Specialist to take ownership of day-to-day administration, tenant communication, tech stack operations, and local business development outreach for our 14-unit portfolio.

This is a primarily text-and-email-based role (minimal phone calls) focused on creating a memorable guest experience. You will manage automated and manual guest communications from check-in to check-out, triage maintenance and Wi-Fi requests, maintain smart lock access, optimize dynamic pricing strategies, and build structured Standard Operating Procedures (SOPs).

Additionally, you will drive business development by executing proactive weekly outreach to our database of 20+ insurance adjusters, housing coordinators, and relocation contacts to maintain high occupancy.

Key Responsibilities

1. Guest Hospitality & Life-Cycle Communication

• Check-In to Check-Out Journey: Oversee guest communications across Airbnb, VRBO, and Furnished Finder with a warm, empathetic tone suited for corporate and relocating tenants.


• Memorable Touchpoints: Ensure key messaging moments (welcome guides, mid-stay check-ins, checkout instructions) leave a lasting impression and capture 5-star reviews, direct stay renewals, and referrals.


• Tenant Maintenance Triage: Handle ad-hoc requests (Wi-Fi troubleshooting, smart lock access, maintenance logs) quickly and coordinate with local Chicago cleaning and maintenance vendors.

2. MTR Tech Stack & Dynamic Pricing Management

• Property Management Systems: Daily management of Hospitable (messaging/automations/channel management) and Furnished Finder.


• Dynamic Pricing: Monitor and adjust rate strategies using PriceLabs based on market demand, seasonality, and stay duration.


• Smart Access Control: Issue and verify guest door codes using our Smart Lock management tools.

3. Business Development & Insurance Lead Outreach

• B2B Partner Outreach: Conduct systematic weekly outreach to our database of 20+ insurance adjusters, relocation agents, and corporate housing contacts to build long-term referral relationships.


• Occupancy Drive: Identify new corporate lead sources to fill listing gaps and secure direct long-term bookings.

4. Systems & Process Standardization

• SOP Development: Help document, build out, and refine operating procedures for vendor dispatch, tenant onboarding, emergency protocols, and lead tracking.

Qualifications & Requirements

• Industry Experience: 2+ years of experience in short-term rental (STR) or mid-term rental (MTR) operations, property management, or corporate housing support.


• MTR Tech Stack Mastery: Hands-on experience with Hospitable, PriceLabs, Furnished Finder, and Smart Lock integrations.


• Communication & Hospitality Tone: Exceptional written English skills with a warm, hospitable, and reassuring communication style suitable for high-end corporate and insurance clients.


• Schedule Alignment: Availability to work a dedicated 8-hour shift during US Central Time (7:00 AM – 5:00 PM CT window).


• Workstation & Redundancy: Dedicated quiet home office, high-speed fiber internet, and power/internet backup systems.