Customer Support Associate

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Chicago, IL
Hybrid
Cloud • Other
Help us revolutionize real estate services.
The Role

Lessen is one of the fastest growing companies in the real estate services industry. Our proprietary technology platform provides clients with portfolio dashboards, the ability to review and approve project estimates, check in on project progress in real time and pay vendors all in one place! But we aren’t just a tech company. We are also a property service delivery company offering renovations, turns and maintenance to residential and commercial clients. Lessen recently acquired SMS Assist, an industry-leading facilities maintenance technology and delivery company. The new combined national footprint will serve more than 250,000 properties, facilitate approximately 2.5 million repair and maintenance orders, and complete nearly 20,000 renovation and turn projects per year. Lessen has quickly evolved from exciting startup to valued partner, delivering scalable and turnkey property services to our clients.


Let’s say a resident has a leaky pipe. That resident can submit a work order request through an app using their smart phone, the website using a desktop computer, or by calling in the request and speaking to one of our customer service representatives. After the work order has been created, our Dispatch Team will qualify the work order, then send it to a qualified plumber. The work order then moves over to our Follow Up Team who will “follow” along with the work order to ensure the leaky pipe gets fixed in a timely manner and the resident is kept updated along the way. 

What You'll Do:

  • Replying to messages from vendors, clients, and residents, and then taking actions in order to move a work order towards completion (40%)
  • Outbound phone calls to vendors to confirm they have capacity and can complete the job within the required timeframe (20% of day)
  • Outbound resident communications via phone, email, and text (20% of day)
  • Work order qualification checking for duplicates, vendor warranties, client direction, and resident responsibility (10% of day)
  • Inbound calls from residents, vendors, and the client (5% of day)
  • Team meetings with a fun team building activity, open forum to ask questions, and review of policy and procedure updates (5% of day)

You Should Have:

  • Critical thinking skills
  • Fast-paced decision making, ability to complete 100-120 follow up tasks per day
  • Attention to detail and adherence to policies and procedures as measured by a weekly quality assurance check
  • Resourceful, know when to reference our internal knowledge base for client-specific business rules, as well as when to reach out to management and other departments for guidance
  • High level of care for our partners; residents, clients, and vendors
  • Ability to adapt to change on a weekly basis due to client needs or updates to our technology
  • Education Level – High school diploma required, Associates or Undergraduate degree preferred


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. 

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The Company
HQ: Scottsdale, Arizona
713 Employees
Year Founded: 1999

What We Do

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. To learn more, visit Lessen.com.

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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About our Teams

Lessen LLC Offices

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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