Full-Time

Vendor Relationship Representative 2

Lessen

Lessen

1,001-5,000 employees

Property services marketplace and SaaS platform

Compensation Overview

$15.87 - $20.63/hr

Chicago, IL, USA

Hybrid

Hybrid work arrangement in Chicago.

Associate's

Category
Operations & Logistics (1)
Required Skills
Customer Service

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Requirements
  • An Associate’s Degree or equivalent work experience is required.
  • Previous experience in a customer service role is preferred.
  • Customer service proficiency is required.
  • Verbal communication proficiency is required.
  • Written communication proficiency is required.
  • Teamwork proficiency is required.
  • Relationship-building proficiency is required.
  • Organizational awareness proficiency is required.
  • Learning agility proficiency is required.
  • Problem-solving proficiency is required.
  • Process orientation proficiency is required.
  • Prioritization proficiency is required.
Responsibilities
  • Develop and maintain positive vendor relations to ensure superior customer satisfaction.
  • Receive and handle customer calls and email requests for services.
  • Manage the scheduling and completion of all services assigned by customers.
  • Manage real-time inquiries and track and respond to commitments to follow up with customer and vendor inquiries.
  • Identify, research, and resolve customer issues using the company’s web-based systems and databases.
  • Source new vendors to perform required services as needed.
  • Resolve or escalate disputes or unsatisfied service confirmations.
  • Maintain open communication with vendors in accordance with contracts and agreed-upon scopes of work throughout the relationship.
  • Provide market intelligence feedback to maximize customer satisfaction and support strategies and policies for attracting and retaining customers.
  • Provide information to supervisors, coworkers, and subordinates by telephone, in writing, by email, or in person.
  • Enter information into the database and ensure consistency and accuracy.
  • Educate clients on the benefits of the Lessen service offering.
  • Resolve client and affiliate issues without escalation whenever possible.
  • Remain on the queue and address all requests.
  • Provide creative solutions to meet client needs and maximize value.
  • Contribute to special projects and continuous improvement initiatives as requested by operations management or the client.
  • Provide management with recommendations for procedure changes as needed.
  • Foster a positive team environment.
  • Ensure the confidentiality of internal and external data.
  • Perform ad hoc projects and other assigned duties.
Desired Qualifications
  • Previous experience in a customer service role.

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

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Simplify Jobs

Simplify's Take

What believers are saying

  • Lessen launched Aiden on May 20, 2026, strengthening AI automation for maintenance operations.
  • Fast Company named Lessen among 2026's Most Innovative Companies, aiding enterprise sales credibility.
  • Chris Lyman's 2026 appointment targets commercial expansion, while benchmark data deepens operator retention.

What critics are saying

  • Lessen listed Chicago subleases in May 2026, signaling cost pressure after expansion.
  • Heavy dependence on HappyCo and Yardi lets incumbents disintermediate Lessen's workflow layer by 2027.
  • SMS Assist integration debt and financing from the $950 million deal leave execution vulnerable.

What makes Lessen unique

  • Lessen's Aiden platform unifies intake, triage, verification, and invoicing across maintenance workflows.
  • HappyCo and Yardi integrations embed Lessen inside operators' existing systems, reducing switching friction.
  • Lessen's network spans 30,000 providers and 3 million annual work orders, creating scale.

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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%
Business Wire
May 20th, 2026
Lessen integrates with HappyCo to streamline multifamily property maintenance and service execution

Lessen, a property services platform, has integrated with HappyCo's maintenance operations platform to streamline multifamily property operations. The partnership connects HappyCo's inspections workflows with Lessen's network of over 30,000 service providers, enabling property teams to initiate and track maintenance work within a single system. The integration allows property teams using HappyCo to trigger service requests through Lessen immediately when issues are identified, reducing manual handoffs and accelerating response times. Real-time data from Lessen's platform syncs back into HappyCo, providing end-to-end visibility from issue identification to work completion. Lessen completes over three million work orders annually, whilst HappyCo's platform manages nearly six million units across North America. The integration is now available through the HappyCo Plugin Marketplace.

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.