Hospitality Manager at Landing 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 segment ownership role. You will manage a segment of our properties in Chicago, IL Market  - member experience, property relationships, housekeeping vendors, maintenance, unit quality, and everything in between. You will oversee reservations made through Landing’s platform as well as OTA partners like Airbnb and Booking.com , build relationships with property partners, resolve member issues across multiple channels, and report on market performance to your Hub Manager.

If you've run or worked in 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 own the whole market segment, not just one property  -  and the playbook is still being written.

This role is for someone who thrives when things are moving fast, makes decisions with incomplete information with the best customer experience in mind, and builds systems while using them.

 

What you'll own

• Reservation management across direct and OTA channels — including Landing bookings and platforms like Airbnb and Booking.com 
• Member experience from booking through checkout  -  tickets, inquiries, escalations
• Property and housekeeping partner relationships
• Market KPIs: NPS, CSAT, cleaning quality, growth
• Reservation coordination and maintenance escalation with property management teams
• Onboarding, installation, and launching of new properties within your market segment

 

What we're looking for

• Background in hotel operations, short-term rental management, vacation rental portfolio management, or high-volume hospitality  -  you know how to operate when guests don't wait
• Experience running a market, property, or operation with real autonomy  -  not just executing someone else's decisions
• Strong organizational and follow through skills  -  tickets don't resolve themselves and this role has a lot of them
• Ability to triage under pressure  -  three things are urgent at once, you know which one to move on first
• Comfort with ambiguity  -  we're a growth-stage company and the answer isn't always written down somewhere

 

Work Schedule & Availability

Core business hours for this role are Monday- Friday, 8am-5pm. As a guest-facing position, additional availability is required, including evenings, weekends, and holidays, based on business needs. These needs may increase during peak periods, such as month-end and high-volume check-in times.

 

What we offer

• Opportunities for upward mobility - we want you to grow with us! Our management team in Field Operations is built from internal promotions.
• Competitive compensation: $55,000–$75,000 base salary (based on experience) + performance bonus of up to 20% of base salary + $6,600 annual vehicle and cell stipend 
• Stock Options
• Comprehensive benefits package: Medical, dental, vision, life, AD&D, disability, mental health, pet, commuter benefits, and FSA or HSA options
• 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.