Full-Time

Customer Escalations Representative 4

Lessen

Lessen

1,001-5,000 employees

Property services marketplace and SaaS platform

Compensation Overview

$20 - $21/hr

Chicago, IL, USA

Remote

Category
Customer Experience & Support (1)
Required Skills
Word/Pages/Docs
Excel/Numbers/Sheets
Requirements
  • High school diploma required
  • Computer Skills: proficiencies in Microsoft Word, Excel, Outlook essential
  • Basic troubleshooting knowledge and ability to articulate
  • Ability to communicate industry language
  • Undergraduate degree / internship preferred
  • Intellectual agility and adaptability
  • Property maintenance experience
  • Trades knowledge
Responsibilities
  • The schedule for this role is 11:00 AM - 8:00 PM on Monday, Tuesday, Wednesday, Saturday and Sunday.
  • Develop and maintain positive client relations as 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; many of the services a Senior CSR will handle will be complex project type work {examples: closed stores or restaurants with multiple Affiliates involved}
  • Act as final escalation point before determining whether any disputes or unsatisfied service confirmations need to be highlighted to Team Lead
  • 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; will be considered a point person for the handoff between shifts and/or other offices
  • May be required to run special reports for the Team Lead and/or Client, as well as provide analysis on performance trends
  • Demonstrate professionalism in communication, relationship development, customer service, etc.
  • Assist in training team members and provides constructive feedback as necessary
  • Provide market intelligence feedback to maximize customer satisfaction and to ensure strategies and policies are in place to attract and retain customers
  • 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
  • Computer Skills: proficiencies in: Microsoft Word, Excel, Outlook essential
Desired Qualifications
  • 4+ years of customer service experience preferred
  • Preferred experience as a CSR III
  • Property maintenance experience
  • Trades knowledge
  • Undergraduate degree / internship preferred
  • Intellectual agility and adaptability
  • Ability to communicate industry language
  • Basic troubleshooting knowledge and ability to articulate

Lessen provides a technology-powered end-to-end platform that connects property owners with a network of verified professionals for maintenance, repairs, and renovations. Its marketplace plus SaaS tools manage bidding, scheduling, payment, and quality control across portfolios. Unlike general property marketplaces, Lessen targets institutional investors, property managers, and real estate owners, offering integrated procurement and portfolio management. Its goal is to simplify and scale property maintenance and renovations, delivering transparent, auditable workflows while generating revenue from transaction fees and software subscriptions.

Company Size

1,001-5,000

Company Stage

Late Stage VC

Total Funding

$1.2B

Headquarters

Scottsdale, Arizona

Founded

2019

Simplify Jobs

Simplify's Take

What believers are saying

  • Aiden AI platform reshapes facilities management for residential and commercial real estate.
  • $170M Series B funding values Lessen over $1B, fueling expansion.
  • Acquisition of Blue Skyre IBE expands global facilities management capabilities.

What critics are saying

  • ServiceChannel's AI platform erodes Lessen's market share in 12-24 months.
  • Jobber captures multifamily clients, cutting Lessen's transaction fees by 20-30% in 6-12 months.
  • Yardi's proprietary module commoditizes Lessen's SaaS fees in 3-6 months.

What makes Lessen unique

  • Lessen integrates Lessen360 with Yardi Voyager for real-time work order synchronization.
  • Lessen Advantage Marketplace provides vendors 18% savings on products via One Source.
  • Lessen serves over 1 million properties with 30,000 vetted vendors nationwide.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

Life Insurance

Disability Insurance

401(k) Retirement Plan

Paid Vacation

Parental Leave

Career Advancement Opportunities

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

0%

2 year growth

0%
France Media
Mar 5th, 2025
Lessen Opens New 76,932 SF Office in Downtown Chicago

Lessen opens new 76,932 SF office in downtown Chicago.

Business Wire
Jan 6th, 2025
Lessen Announces Integration with Yardi, Offering Seamless Access to On-Demand Services and Maintenance Solutions

Lessen360(TM), a cloud-based platform purpose-built for centralized maintenance operations, is now fully integrated with Yardi Voyager, enabling real-time synchronization of work orders and make-readies between the platforms.

Business Wire
Apr 2nd, 2024
Lessen Launches Innovative Purchasing Marketplace For Vendors

SCOTTSDALE, Ariz.--(BUSINESS WIRE)--Lessen, the premier tech-enabled, end-to-end solution for outsourced real estate property services, today announced the launch of the “Lessen Advantage Marketplace.” This centralized, dynamic hub allows vendors who are part of the Lessen Advantage™ community to enjoy access to a diverse range of products and services geared toward maximizing efficiency and fostering growth. The Marketplace includes access to preferred rates on insurance and bank financing, as well as access to thousands of products and materials through One Source, an integrated e-commerce purchasing hub. On average, users will benefit from savings of over 18% compared to prevailing retail prices. "We want to help our vendor community to save time and money on all of their projects,” said Lessen founder and CEO Jay McKee. "Our marketplace is another step forward in our goal to transform how property services are managed.”

Business Wire
Nov 30th, 2023
Real Estate Marketplace Platform Lessen Closes $170 Million Series B Funding Round

Lessen announces that it has closed a $170 million Series B funding round along with a company valuation of more than $1 billion.

The Business Journals
Sep 27th, 2023
First look: Scottsdale-based proptech firm expands into new amenity-filled headquarters

Scottsdale-based Lessen Inc. will stay within the city but has moved offices from 4021 N. 75th Street into the Portales Corporate Center I at 4800 N. Scottsdale Road.