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Operations Support Coordinator

Lessen
3 days ago
Full-time
On-site
Chicago, Illinois, United States
Real Estate Admin

Operations support roles at property tech companies like Lessen sit in an interesting middle space. You're not out in the field, but you're often the reason field work actually gets done correctly and on time. This coordinator position is specifically built around the more complex end of the work order pipeline, which means you're handling the situations that a standard dispatch queue can't just process and move on from.

What This Role Actually Involves

The core of the job is managing project-level work orders and escalations that require more coordination than a typical service request. You'll be sequencing and linking work orders so that jobs happen in the right order, keeping vendors informed, and making sure residents have the information they need about scheduled appointments. That sounds straightforward until you're juggling real-time calls and emails while tracking open commitments across multiple active projects.

You'll also serve as a shift handoff point, which means your notes and database entries need to be accurate enough for someone else to pick up exactly where you left off. Sloppy documentation at this level creates downstream problems for the field team, the vendor, and eventually the resident. Consistency here isn't a soft skill. It's a job requirement.

  • Coordinate scheduling and completion of project work orders, ensuring proper sequencing across all linked orders
  • Act as vendor liaison and project manager for complex or sensitive service situations
  • Handle inbound calls and emails from residents and clients while managing open commitments in real time
  • Serve as a final escalation point before issues are elevated to a Team Lead or Affiliate Market Manager
  • Maintain communication with affiliate vendors in alignment with contracted scope of work
  • Enter and verify data in Lessen's One platform with a focus on accuracy and consistency
  • Provide feedback to leadership on process improvements and market intelligence
  • Assist in training teammates and contribute to a constructive team environment

What You'll Need

Four or more years of customer service experience is preferred, particularly in dispatch, CSR, or customer service associate roles where you were measured on performance metrics. Proficiency in Microsoft Office is required. Familiarity with property maintenance workflows or trades knowledge is a genuine plus here, not just a nice-to-have, because you'll be communicating with vendors and residents using industry-specific language and you need to understand what you're coordinating.

Shift flexibility is listed as a requirement, so it's worth being clear-eyed about that. This type of operations role often means coverage outside standard business hours depending on how Lessen structures its support model. If you've worked dispatch before, this won't surprise you.

What Separates Strong Candidates

The candidates who do well in roles like this tend to be people who are comfortable making judgment calls under pressure without waiting for someone to tell them exactly what to do, while also knowing when an issue genuinely needs to go up the chain. That balance between autonomy and escalation awareness is harder to find than most job postings acknowledge. If you've managed escalations in a high-volume environment and have some background in property maintenance or vendor coordination, you're already ahead of most applicants.

Experience with Lessen's One platform is strongly preferred, which suggests internal candidates or people who've worked within Lessen's ecosystem will have a real advantage at the start. That said, the skills you build here, vendor management, escalation handling, work order coordination, transfer well to operations roles across third-party property management and single-family rental at scale, which is exactly the segment Lessen operates in.