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Team Lead

Lessen

Chicago, IL · $50k–$58k a year · Posted October 27, 2026

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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.