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Somewhere is seeking a warm, process-driven Short-Term Rental Operations Specialist to own day-to-day administration, guest communications, and pricing management for a 14-unit portfolio. The role focuses on text-and-email interactions, check-in/out, SOP development, and vendor coordination to deliver a premium guest experience.
You will also drive weekly business development outreach to insurance adjusters, relocation contacts, and corporate housing pros to maintain high occupancy and direct
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
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.