Field Operations Inspector

Overview: CYM Living - Where caring meets innovation. We are a national real estate firm with corporate headquarters in Chicago, IL, Indianapolis, IN, and just outside of New York City. Our mission is to provide our residents with an exceptional living experience, nurture a culture of community, and empower growth from within. As a vertically integrated firm, we lead with operations by taking a hands-on approach to real estate investment and property management. We accomplish our mission by incorporating data and technology with hyperlocal customer service to all units.

We are hiring a Field Operations Inspector to walk and inspect scattered-site multifamily buildings throughout Chicago. This is a high-activity, boots-on-the-ground role focused on identifying maintenance issues, auditing completed work, and holding teams accountable to building standards. .

If you’re comfortable being on your feet all day, walking multiple buildings, and climbing stairs repeatedly, this role is for you.

What You’ll Be Doing (Daily)

• Walk multiple scattered-site apartment buildings across Chicago
• Inspect common areas, hallways, stairwells, basements, vacant units, and exteriors
• Identify maintenance, safety, and cleanliness issues
• Audit maintenance and vendor work to confirm issues are fully completed; not just marked done
• Re-walk prior issues to ensure proper follow-through
• Take photos, document findings, and submit clear reports
• Communicate issues directly to on-site and maintenance teams

Work Breakdown

• 90% field work – walking buildings, inspections, re-checks
• 10% office/admin – documentation, reporting, follow-ups

Ideal Candidate

• Doesn’t mind stairs, extensive walking, or working outdoors
• Notices issues others overlook and take ownership to ensure they’re resolved
• Holds teams accountable and consistently follows up until work is completed correctly
• Comfortable navigating Chicago neighborhoods and scattered-site properties
• Communicates clearly and professionally with maintenance teams, vendors, and internal staff
• Strong follow-up skills with the ability to track issues through completion
• Works well as part of a team while also being self-directed in the field

Requirements

Physical & Field Requirements

• On your feet most of the day
• Climbing staircases repeatedly
• Walking long distances in and between buildings
• Working in all types of Chicago weather conditions

Must-Have Requirements

• Reliable vehicle and valid driver’s license (daily travel between scattered sites required)
• Comfortable working independently in the field
• Strong attention to detail and follow-through
• Able to use a phone or tablet for photos, checklists, and reporting
• Prior experience in property management, maintenance, construction, inspections, or facilities is a plus

Benefits

We offer our full-time employees a comprehensive benefits package that includes:

• Medical, Dental, and Vision Coverage
• Flexible Spending and Health Savings Accounts
• Short-Term Disability and Supplemental Life Insurance
• Employee Assistance Program
• Fitness and Well-Being Program
• Company-Paid Life Insurance and Long-Term Disability
• 401(k) with Generous Company Match
• Paid Time Off (PTO), Paid Sick Time, and Paid Holidays

How to Apply:
Please submit your resume and cover letter detailing your qualifications and interest in the Field Operations Inspector at CYM Living. We look forward to reviewing your application and discussing how you can contribute to our team.

CYM Living is an equal opportunity employer.

SALARY RANGE: $75 - $80K per year