Operations Lead - Chicago

Redefining how people live. At Blueground we believe that when your base is reliable, the world opens up. That’s why we’re building the world’s leading platform for living. Every year, 350 million people move between cities—yet today’s housing options haven’t caught up with the needs of this modern, mobile generation. Blueground was built to change that. With 40,000+ homes across the globe, available for stays from a few days to a year or more, we’re just getting started. We’re on an exponential growth path to redefine living and create an entirely new category. Our edge? Powerful proprietary tech, operational excellence, and a team that executes with speed and discipline. Our culture is grounded in five principles: Guests First – Every decision starts with their experience. Move Fast – We value speed, momentum, and action. Dive In – The magic is always in the details, and we go deep. Embrace Change – Change isn’t a disruption; it’s how we grow. Keep It Honest – Transparency accelerates progress—and strengthens relationships. If you’re ready to do the best work of your life and help reshape how the world lives, we’d love to meet you. The Role We’re looking for a proactive, detail-oriented Operations Lead to join our fast-growing team in Chicago, IL. This field-based role is ideal for someone who thrives on solving problems, leading by example, and ensuring every property meets the highest standards of quality and guest satisfaction. What You’ll Do Lead Property Turnovers: Oversee the full apartment preparation process—from coordinating housekeeping and maintenance teams to conducting detailed inspections before guest check-ins. Own Onsite Readiness: Assemble furniture, troubleshoot WiFi and tech setups, and carry out small repairs to ensure every apartment meets our standards before move-in. Field Coordination & Team Supervision: Act as the go-to person in the field, managing relationships with external vendors, housekeeping staff, and building personnel to ensure seamless operations. Perform Quality Control: Conduct thorough property inspections using mobile checklists, flag issues, and ensure that every space meets our cleanliness, functionality, and design expectations. Hands-On Support: Step in to help with urgent needs—whether that’s swapping out furniture, fixing appliances, delivering essentials, or solving guest lockouts. Drive Efficiency: Manage and maintain our corporate vans and inventory stock, ensuring supplies and tools are always available and organized Each day begins at the office, where you pick up your equipped "Pit Stop Van" before heading out into the city. Your tasks are clearly scheduled, ensuring efficiency as you complete 3–4 full unit turns. Upon arriving at each unit, you conduct a detailed inspection, addressing any maintenance needs, assisting with some housekeeping alongside the cleaning team, and preparing the space for the next guest. Whether troubleshooting appliances, replacing keys, or refreshing paint, every step ensures the unit meets high-quality standards. Once the first unit is ready, you drive to the next property and repeat the process, adapting to each location’s unique needs. Throughout the day, you coordinate logistics, problem-solve on-site challenges, and maintain a smooth workflow. Finally, after completing all scheduled turns, you return the van to the office, wrapping up a productive day of ensuring seamless guest experiences. 2–3 years of experience in a supervisory or team lead role—ideally in field ops, facilities, hospitality, or housekeeping Comfortable performing basic handyman tasks and minor repairs Physically capable of lifting 30Ibs and being active for most of the workday Tech-savvy—familiar with tools like Slack, G Suite, and mobile apps Strong communicator with a customer-first mindset and a positive, can-do attitude A flexible team player who thrives in a dynamic, constantly evolving environment Additional Requirements: Availability to work SAT/SUN/MON Valid driver’s license Ability to drive a company van-sized vehicle Access to a reliable vehicle (DC/SEA/LA/SF/SAN) with mileage reimbursement Competitive salary and annual performance bonus ($52,000 - $63,250 with up to 15% performance bonus) Handheld device stipend Flexible PTO Cigna Health Insurance (Medical, Dental, Vision) 401k retirement plan Paid maternity/parental leave benefits for new parents Complimentary accommodation in Blueground locations. Think summer in Greece and winter in Dubai!

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