Team Lead
Lessen
Chicago, IL · $50k–$58k a year · Posted October 27, 2026
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November 2026
- #1Best cities for government pay after cost of living$146k · of 18
- #1Cities with the most jobs that do not need a four-year degree in the Midwest684 jobs · of 51
- #1Cities with the most jobs that do not need a four-year degree in the Great Lakes684 jobs · of 36
- #1Best cities for software and engineering jobs in the Midwest1,140 openings · of 59
- #1Best cities for software and engineering jobs in the Great Lakes1,140 openings · of 48
- #1Best all-round cities for mid-career professionals in the Midwest80 / 100 · of 20
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About the job
Lessen is the tech-enabled, end-to-end property service provider that is transforming how commercial and residential real estate services are delivered and managed at scale. Lessen’s technology platform provides data-driven insights that unlock key growth opportunities for the entire real estate ecosystem—including investors, owners, managers, and service providers. The company leverages a network of over 30,000 vetted, qualified vendors (Lessen Affiliates) serving clients with over 1 million properties and completing more than 3.5 million work orders annually across an expanding range of services. Lessen, LLC is a venture-backed, privately held company with offices in Scottsdale and Chicago.
What You'll Do:
Assist in the coordination and execution of the complete work order life cycle from creation to resolution
Manage vendors to ensure services are completed within agreed upon SLA’s
Collaborate with District Lead to work cross-functionally with other teams to manage vendors in region(s)
Develop client relationships; collaborate with key stakeholders in markets to devise solutions to client issues
Assist in monthly reporting, forecasting and asset management on all sites
Help develop and implement preventative, ongoing and anticipated maintenance/repair programs
Assist with development of operating and capital budgets for the assigned
Support the creation of work order forecasts by drawing on historical, current, and metric-based data
Attend regular client status meetings, if applicable
Ensure confidentiality of internal and external data
Perform ad-hoc projects and other duties as assigned
What You'll Need:
Bachelor’s degree or equivalent facilities management experience
3+ years of facilities management experience
Experience with managing multiple vendors for day-to-day work order management and small to large capital projects
Client relationship management skills
Communication and organizational skills
Why Lessen: · Competitive compensation · Health, Dental, Vision, Life, Disability options · 401K retirement savings plan · Paid vacation, federal and floating holidays · Maternity/Paternity Pay · Career advancement opportunities · All the tools you'll need to be successful
Lessen is intentional about attracting, developing, and retaining amazing talent from diverse backgrounds. We’re looking for teammates that are enthusiastic, empathetic, curious, motivated, reliable, and will help us amplify the positive & inclusive culture we’ve been building. Lessen is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran or disabled status, or genetic information.