Task Force Operations Manager Jobs in Chicago, IL

About Landing

Since 2019, Landing has built the largest flexible living network in the country - 35+ markets, thousands of apartments, no deposits, no hassle. We're growing fast and operating in the real world, which means things move quickly, priorities shift, and no two days look the same.

About the role

This is a market coverage and operations role. As a Task Force Manager, you will deploy into Landing markets across the US — wherever the business needs you — and step in as the sole operator when a General Manager is on leave. That means owning the full market: member experience, property relationships, housekeeping and maintenance coordination, unit quality, and performance reporting. You will cover operations for one to three weeks at a time, maintain key account relationships, and hand markets back off cleanly when the assignment ends. Travel locations are driven entirely by business need, so being positioned near a major hub is essential to moving quickly when an assignment comes in.

If you've run a hotel, a short-term rental portfolio, or a high-volume hospitality operation, you already know what this job feels like. The difference here is that you're stepping into someone else's market and making it run like your own — with no ramp-up time and no room to wait and see.

This role is for someone who moves fast, makes decisions under pressure, and builds trust quickly with people they've just met. Candidates based in Chicago are strongly preferred given proximity to major airports and ease of access to Landing's remote markets.
 

What you'll own

• Full market operations during GM leave — member experience, property relationships, vendor coordination, and maintenance escalations
• Member support tickets and communications across all channels
• Liaison with property management teams to resolve maintenance requests, address member concerns, and execute new leases
• Market KPIs: NPS, CSAT, cleaning quality, and market growth
• Unit quality evaluation — ensuring every home meets Landing standards before move-in
• Relationships with key property accounts for the duration of each assignment
• Market growth: coordination and installation of new Landing homes within assigned markets
• Critical preparation and coordination for VIP guest bookings
• Smooth handoff coordination with the AGM and Hub Manager at the start and end of every assignment
• Auxiliary training responsibilities when not actively on assignment
   

What we're looking for

• 2+ years of background in hotel operations, short-term rental management, or high-volume hospitality — you know how to operate when members don't wait
• Experience running a market, property, or operation with real autonomy — not just executing someone else's playbook
• Bias for action — when things go sideways, you move toward the problem, not away from it
• Strong organizational skills and follow-through — you're managing multiple properties, tickets, and relationships simultaneously across markets you didn't build
• Ability to triage under pressure — three things are urgent at once, you know which one to move on first
• Comfort with ambiguity and travel — 80% travel is required, and the assignment always comes with surprises
• Exceptional communication and interpersonal skills — you build credibility fast with people at all levels
   

Work Schedule & Availability

This role requires 80% travel. When on assignment, you are the market owner, which means availability extends beyond standard business hours based on operational needs — including evenings, weekends, and holidays. Demand increases around month-end and high-volume check-in periods.
 

What we offer

• Opportunities for upward mobility — our Field Operations management team is built from internal promotions
• Competitive compensation: $75,000 base salary
• Stock options
• Comprehensive benefits - Medical, Dental, Vision, Life and AD&D, Disability, Mental Health, Pet, Commuter, and FSA or HSA
• Retirement support: 401(k) plan + access to ImmediatePay
• Generous paid time off policy to support work-life balance
• Travel perk: $750 USD annually in Landing Stays

Landing is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, including pregnancy, sexual orientation, gender identity, and related conditions, national origin, age, disability, genetic information, military service or obligation, or any other status protected by applicable federal, state, or local law

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