Lessen LLC Jobs

Customer Service Representative

Lessen LLC

Customer Service Representative

Posted 19 Hours Ago

Hiring Remotely in Chicago, IL, USA

Remote or Hybrid

Mid level

Cloud • Real Estate • Software • PropTech

Help us revolutionize real estate services.

The Role

Serve as primary liaison between clients and vendor network to manage repair and maintenance requests via phone and email. Schedule work, track commitments, escalate disputes, update the database, maintain professional client/vendor communication, assist team training, and handle ad-hoc projects while ensuring data accuracy and confidentiality.

Summary Generated by Built In

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

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.

Skills Required

High school diploma
3-4 years customer service experience
Basic troubleshooting knowledge and ability to articulate
Ability to communicate industry language
Proficiency in Microsoft Word, Excel, Outlook
Work schedule: Monday–Friday, 1:00 PM–10:00 PM Central Time
Shift flexibility may be required

What the Team is Saying

Lessen LLC Compensation & Benefits Highlights

Healthcare Strength — Medical, dental, and vision coverage are paired with an employee assistance program offering on‑demand counseling, plus wellness programming/classes. Disability and life insurance are also included as part of the core package.
Leave & Time Off Breadth — Flexible or “unlimited” PTO, paid parental leave, family medical leave, and volunteer time are part of the offering. These options point to broad time‑away support across categories.
Retirement Support — A 401(k) with company match is available as part of the financial benefits. Pre‑tax savings options and related financial protections round out the package.

Learn more about Lessen LLC's Compensation & Benefits →

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The Company

HQ: Scottsdale, Arizona

713 Employees

Year Founded: 1999

What We Do

Why Work With Us

We make caring for and improving properties simpler, faster, better. Powered by tech and perfected by people, we deliver best-in-class, transformational solutions to deliver assets to market faster, keep businesses up and running, and improve customer and resident experiences. We're property services, simplified.

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Lessen LLC Teams

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Residential

Commercial

Lessen Direct - A Mobile Technician Workforce

About our Teams

Lessen LLC Offices

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Hybrid Workspace

Employees engage in a combination of remote and on-site work.

At Lessen, managers decide how teams work best—office, home, or hybrid. We value flexibility, connection, and outcomes, investing in tools that keep everyone aligned and focused on delivering great results together.

Typical time on-site: 3 days a week

HQScottsdale, AZ

Chicago, IL

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