[Hiring] Short-Term Rental Operations Specialist @Somewhere

Role Description

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

• Guest Hospitality & Life-Cycle Communication
  • Oversee guest communications across Airbnb, VRBO, and Furnished Finder with a warm, empathetic tone suited for corporate and relocating tenants.
  • 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.
  • Handle ad-hoc requests (Wi-Fi troubleshooting, smart lock access, maintenance logs) quickly and coordinate with local Chicago cleaning and maintenance vendors.
• MTR Tech Stack & Dynamic Pricing Management
  • Daily management of Hospitable (messaging/automations/channel management) and Furnished Finder.
  • Monitor and adjust rate strategies using PriceLabs based on market demand, seasonality, and stay duration.
  • Issue and verify guest door codes using our Smart Lock management tools.
• Business Development & Insurance Lead Outreach
  • Conduct systematic weekly outreach to our database of 20+ insurance adjusters, relocation agents, and corporate housing contacts to build long-term referral relationships.
  • Identify new corporate lead sources to fill listing gaps and secure direct long-term bookings.
• Systems & Process Standardization
  • Help document, build out, and refine operating procedures for vendor dispatch, tenant onboarding, emergency protocols, and lead tracking.

Qualifications

• 2+ years of experience in short-term rental (STR) or mid-term rental (MTR) operations, property management, or corporate housing support.
• Hands-on experience with Hospitable, PriceLabs, Furnished Finder, and Smart Lock integrations.
• Exceptional written English skills with a warm, hospitable, and reassuring communication style suitable for high-end corporate and insurance clients.
• Availability to work a dedicated 8-hour shift during US Central Time (7:00 AM – 5:00 PM CT window).
• Dedicated quiet home office, high-speed fiber internet, and power/internet backup systems.