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Customer Support Associate

LessenChicago, Illinois, United StatesHybrid, Onsite
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 successfulLessen 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. Apply for this job

Life at Lessen

Lessen is the fastest growing startup in the real estate services market. We are building a two-sided marketplace that solves a clear set of customer and vendor needs. We connect real estate owners to timely property services such as renovations, maintenance, and cleaning on one side and service providers to high-quality, well-defined projects with same-day payments on the other. We are fundamentally changing how real estate services are initialized, managed, and delivered at scale. Lessen is on an amazing trajectory – we are well-funded by top Silicon Valley VCs, have committed clients, fast-growing revenue, and a well-defined roadmap.
Thrive Here & What We Value1. Competitive Compensation Package2. Dental, Vision, Life, Disability Options Available3. 401K Retirement Savings Plan Offered4. Paid Vacation, Federal and Floating Holidays Provided5. Maternity/Paternity Pay Available6. Career Advancement Opportunities Available7. Positive & Inclusive Culture8. Diverse Talent Attraction, Development, Retention9. Equal Opportunity Employer
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