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Senior Insurance Field Inspector Jobs in Chicago, IL

CYM Living LLC

Field Operations Inspector

Chicago, IL · On-site

Company-Paid Life Insurance and Long-Term Disability * 401(k) with Generous Company Match * Paid ... Field Operations Inspector at CYM Living. We look forward to reviewing your application and ...

ERM

Inspectors (Field Based)

Rolling Meadows, IL

$28 - $35/hr

The role of an Inspector working within this program requires the use of multiple methods to ... insurance to benefits eligible * employees. *Benefits Eligibility is limited to Regular employees ...

D escoto Inc

Civil Construction Inspector

Chicago, IL · On-site

$45 - $65/hr

... field quality measurement, project documentation including daily written and photo documentation ... Senior inspectors may supervise other inspectors. All inspector positions will act under the ...

D escoto Inc

Civil Construction Inspector

Chicago, IL · On-site

$45 - $65/hr

... field quality measurement, project documentation including daily written and photo documentation ... Senior inspectors may supervise other inspectors. All inspector positions will act under the ...

Rose Paving

Field Analyst

Villa Park, IL · On-site

$60K - $70K/yr

Along with a competitive salary, we offer comprehensive benefits, including health insurance (PPO ... What you'll be doing The Field Inspector plays a key role in maintaining the quality and integrity ...

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All JobsInsurance Field Inspector JobsSenior Insurance Field Inspector JobsSenior Insurance Field Inspector Jobs in Chicago, IL

Senior Insurance Field Inspector information

See Chicago, IL salary details

$31.4K

$77.5K

$136.5K

How much do senior insurance field inspector jobs pay per year?

As of Aug 21, 2026, the average yearly pay for senior insurance field inspector in Chicago, IL is $77,547.00, according to ZipRecruiter salary data. Most workers in this role earn between $56,100.00 and $96,800.00 per year, depending on experience, location, and employer.

How much do senior insurance field inspectors make?

Senior insurance field inspectors typically earn between $50,000 and $70,000 annually, depending on experience, location, and employer. They often perform on-site inspections, assess risk, and may require certifications or specialized knowledge of insurance policies and inspection tools.

What does a senior insurance field inspector do?

A senior insurance field inspector evaluates property and risk conditions by inspecting homes, businesses, or vehicles to determine insurance coverage and claim validity. They document findings, assess damages, and ensure compliance with policy requirements, often using tools like cameras and inspection checklists. This role requires strong attention to detail, knowledge of insurance policies, and sometimes certifications in property inspection or risk assessment.

What are the most commonly searched types of Insurance Field Inspector jobs in Chicago, IL?

The most popular types of Insurance Field Inspector jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Senior Insurance Field Inspector jobs?

Cities near Chicago, IL with the most Senior Insurance Field Inspector job openings:

Senior Insurance Field Inspector jobs near you

Field Operations Inspector

CYM Living LLC

Chicago, IL • On-site

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 22 days ago

Job description

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

Apply