Associate Operations Manager (Chicago)

ROLE DETAILS

• Chicago based - 1 day in office
• 40 hrs/wk
• $20-$30/hr (contract role)

COMPANY OVERVIEW

We are a short-term rental and boutique hotel company operating upscale apartments across major U.S. cities. We partner with luxury multi-family buildings to offer high-end stays for business and leisure travelers.

POSITION SUMMARY

We’re hiring an Associate Operations Manager to serve as the right hand to our head of operations. You’ll be trained on nearly everything it takes to run the company day-to-day: from onboarding properties to managing remote teams, to solving guest issues, coordinating vendors, and improving internal processes. In time, you’ll be able to run operations independently so leadership can focus on business development and scaling.

We’re looking for someone who thrives in ambiguity, knows how to prioritize when everything feels important, and knows how to troubleshoot and keep cool when systems break, timelines shift, or team members need backup.

This role also requires strong customer service instincts—you’ll handle guest escalations directly and ensure issues are resolved in a way that protects our OTA listings and brand reputation.

RESPONSIBILITIES

• Help manage the daily operations of 100+ short-term rentals across multiple cities
• Get hands-on with onboarding new units, guest escalations, maintenance coordination, and team accountability
• Handle sensitive guest escalations and reviews to preserve our Airbnb, Vrbo, and other OTA performance and ratings
• Manage a team of remote and on-site staff; track performance, answer questions, and step in when needed
• Improve and maintain internal systems, SOPs, and processes to help the business run smoother as we scale
• Work across many tech platforms daily (Guesty, Slack, Google Sheets, Asana, Sifely, PriceLabs, and others)
• Be the first line of defense for anything operational, and step up as a decision-maker over time

QUALIFICATIONS

• At least 3 years of experience in operations, logistics, hospitality, or similar
• At least 3 years of experience managing a team
• Strong tech literacy - you should be confident navigating many different software tools and spreadsheets, learning new systems quickly and teaching others how to use said systems
• Excellent prioritization skills and ability to keep calm when juggling a dozen moving parts
• A high bar for quality. You don’t just complete a task or fix an issue, your goal is to improve the process going forward.
• Strong communication skills and experience with customer escalations, especially in high-stakes or emotionally charged situations

NICE TO HAVE

• Experience in short-term rentals or property management
• Experience managing offshore teams

COMPENSATION & BENEFITS

• Hourly rate: $20-$30/hr
• Schedule: Flexible and capable of working remotely in an efficient and diligent manner. This is a full-time, contract role.
• Other requirements: We expect you have a home office with a modern workstation set up, including a fast and reliable internet connection