SECTION I · THE BRIEF
Brief #08672Updated 14 AUG 2026CHICAGO, ILLeverKHOSLA VENTURES
Employbl Company Profile

Customer Service Representative

Lessen is an online platform for managing properties and maintenance services.

Location
Chicago, IL
Company size
Posted
2w ago
Via
Lever
Section II · Full ProfileFree with an account
  • 01Comp band & equity packageLocked
  • 02Seniority & experience requirementsLocked
  • 03Interview process & rubricLocked
  • 04Hiring manager & team contextLocked
  • 05Growth trajectory in this roleLocked
  • 06Offer & decision timelineLocked

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Lessen logo

Customer Service Representative · Lessen

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Job title
Customer Service Representative
Job location
Chicago, IL
Job description
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.
What You'll Do:
• 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
What You Need:
• 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
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Where this role is based

Chicago, IL

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Lessen headquarters

Scottsdale, AZ

Founded

2019

Total raised

$735,000,000

View company profile ↗

Funding rounds

  • Series Unknown$500M

    Koch Ventures, Monroe Capital, Varde Partners, Navitas Capital +1 more

  • Series B$30M

    Legacy Knight

  • Series B$170M

    Fifth Wall, Khosla Ventures, General Catalyst, Navitas Capital

  • Series A$35M

    Fifth Wall, Navitas Capital, Khosla Ventures, General Catalyst