Lessen1d ago

New

USD 20–21.8/yr

Customer Service Representative

United States·ChicagoRemoteFull Time Employeemid

Customer Support SpecialistCustomer

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Quick Summary

Overview

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.

Technical Tools

Customer Support SpecialistCustomer

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.

The Customer Service Representative acts as a liaison between our clients and our network of vendors by managing all our clients’ repair and maintenance needs within our technology platform, One by Lessen. This role communicates predominantly on the phone and electronically with clients and vendors to ensure all maintenance services are completed in an effective and efficient manner.

This is role will work Monday - Friday 1:00 PM - 10:00 PM Central Time.

• Develop and maintain positive client relations required to ensure superior client satisfaction

• Receive and handle customer calls and email requests for services

• Manage real-time inquires while keeping track of and responding to commitments

• Manage the scheduling and completion of all services assigned by customers

• Escalate all disputes or un-satisfied service confirmations in a timely manner

• Remain on the queue and address all requests and customer questions

• Maintain open communication with affiliates in a manner that adheres to all contracts and agreed upon Scope of Work throughout the duration of the relationship

• Provide information to supervisors, co-workers, and subordinates by telephone, in written form, e-mail, or in person

• Enter information into our database and ensure consistency and accuracy

• Demonstrate professionalism in communication, relationship development, customer service, etc.

• Assist in training team members and provides constructive feedback as necessary

• Shift flexibility may be required

• Foster a positive team environment

• Ensure confidentiality and accuracy of internal and external data

• Perform ad-hoc projects and other duties as assigned

• High school diploma required

• 3-4 years of customer service experience preferred

• Basic troubleshooting knowledge and ability to articulate

• Ability to communicate industry language

• Computer Skills: proficiencies in: Microsoft Word, Excel, Outlook essential

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.

Location & Eligibility

Where is the job

Chicago, United States

Remote within one country

Who can apply

Listing Details

Posted: August 14, 2026
First seen: August 14, 2026
Last seen: August 16, 2026

Posting Health

Days active: 0
Repost count: 0
Trust Level: 87%
Scored at: August 14, 2026

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Lessen

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Lessen is a tech-enabled, end-to-end property service provider that is transforming how commercial and residential real estate services are delivered and managed at scale.

Employees

3k+

Founded

2019

Domain

lessen.com

Jobs

View 66 jobs

View company profile

Salary

USD 20–21.8

per year