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Roofing Insurance Jobs in Chicago, IL (NOW HIRING)

Simon Roofing

Roofing Service Tech

Gary, IN · On-site

$23 - $29/hr

Roofing Service Technician We are looking for a Roofing Service Technician to join our organization ... GREAT BENEFITS - Paid Time Off, Health Insurance, Dental, Vision Care benefits, Free life insurance ...

Simon Roofing

Roofing Service Tech

Gary, IN · On-site

$23 - $29/hr

Roofing Service Technician We are looking for a Roofing Service Technician to join our organization ... GREAT BENEFITS - Paid Time Off, Health Insurance, Dental, Vision Care benefits, Free life insurance ...

Apple Roofing

Roofing Sales Representative

Chicago, IL · On-site

You'll be the face of Apple Roofing in your community - meeting homeowners, inspecting roofs, and guiding customers through the insurance and sales process with integrity and confidence. What you'll ...

Peach State Roofing

Be Seen First

Commercial Roofing Sales Representative

Batavia, IL · On-site

Health, Dental, Vision, Disability and Life Insurance * Company vehicle and cell phone * PTO and Holidays * 401K with Company Match What We're Looking For * Prior sales experience, commercial roofing ...

Erie Home

Roofing Contractor

Waukegan, IL · On-site

$350K - $750K/yr

General Liability Insurance * Workman's Compensation Insurance * EIN Letter * Current Contractor's License (if required by your state) * Reliable vehicle, roofing tools, and equipment required for ...

Erie Home

Roofing Contractor

Lombard, IL · On-site

$350K - $750K/yr

General Liability Insurance * Workman's Compensation Insurance * EIN Letter * Current Contractor's License (if required by your state) * Reliable vehicle, roofing tools, and equipment required for ...

M&M

Commercial Roofing Foreman

Crete, IL · On-site

$25.50 - $35.25/hr

Benefits Health Insurance Dental and Vision Insurance 401K Ongoing Learning and Development Opportunities Team Outings Volunteer Opportunities About M&M Roofing: M&M Roofing is a full-service ...

Erie Home

Erie Home - Roofing Contractor

Lombard, IL

$26.25 - $36/hr

General Liability Insurance * Workman's Compensation Insurance * EIN Letter * Current Contractors License (if required by your state) * Reliable vehicle, roofing tools, and equipment required for job ...

Erie Home

Erie Home - Roofing Contractor

Waukegan, IL

$25.50 - $35/hr

General Liability Insurance * Workman's Compensation Insurance * EIN Letter * Current Contractors License (if required by your state) * Reliable vehicle, roofing tools, and equipment required for job ...

Storm Guard

Roofing Sales Representative

Westmont, IL · On-site

$70K - $100K/yr

On a routine basis, Roofing Sales Representatives will generate leads by door-knocking, prospecting insurance agents, and gaining referrals from current and previous customers. High-performing Sales ...

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Showing results 1-20

All JobsRoofing Insurance JobsRoofing Insurance Jobs in Chicago, IL

Roofing Insurance information

See Chicago, IL salary details

$26.3K

$81.7K

$127.7K

How much do roofing insurance jobs pay per year?

As of Aug 27, 2026, the average yearly pay for roofing insurance in Chicago, IL is $81,702.00, according to ZipRecruiter salary data. Most workers in this role earn between $60,800.00 and $98,400.00 per year, depending on experience, location, and employer.

What is roofing insurance?

Roofing insurance is a specialized type of business insurance designed for roofing contractors and companies. It typically includes general liability coverage, workers’ compensation, and sometimes commercial auto insurance, all tailored to the unique risks faced in the roofing industry. This insurance protects roofing professionals from financial losses due to accidents, property damage, bodily injuries, and legal claims that may occur during roofing projects. Having roofing insurance is often required by law or by clients to ensure safety and accountability. It also helps roofing businesses maintain credibility and trust with customers.

What are the key skills and qualifications needed to thrive in roofing insurance?

To succeed in roofing insurance, you need a solid understanding of property insurance policies, claims assessment, and roofing systems, often supported by experience in insurance or construction and relevant licensing. Familiarity with claims management software, estimating tools like Xactimate, and industry regulations is typically required. Strong negotiation, attention to detail, and customer service skills set top professionals apart in this field. These competencies ensure accurate claims processing, client satisfaction, and compliance with industry standards.

What are common challenges faced by professionals working in roofing insurance, and how can they be addressed?

Professionals in roofing insurance often encounter challenges such as accurately assessing roof damage, differentiating between storm-related issues and pre-existing wear, and managing claims fraud. Staying updated on roofing materials, building codes, and the latest inspection technologies is crucial for accurate evaluations. Collaborating closely with contractors, adjusters, and policyholders can help clarify claim details and ensure fair outcomes. Ongoing training and clear communication are key strategies for addressing these common hurdles.

What is the difference between Roofing Insurance vs Roofing Estimator?

AspectRoofing InsuranceRoofing Estimator
Required CredentialsInsurance licenses, knowledge of policiesConstruction knowledge, estimating certifications
Work EnvironmentInsurance claims, client consultationsOn-site inspections, project cost estimation
Employer & Industry UsageInsurance companies, adjustersRoofing contractors, construction firms
Common Search & ComparisonRoofing Insurance vs Roofing Estimator

Roofing Insurance professionals focus on assessing insurance claims, understanding policies, and working with insurance companies. Roofing Estimators prepare project cost estimates, inspect sites, and work directly with roofing contractors. While both roles require knowledge of roofing, their primary functions and work environments differ significantly, making them distinct careers within the roofing industry.

What are popular job titles related to Roofing Insurance jobs in Chicago, IL?

For Roofing Insurance jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Roofing Insurance jobs in Chicago, IL look for?

The top searched job categories for Roofing Insurance jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Roofing Insurance jobs?

Cities near Chicago, IL with the most Roofing Insurance job openings:

Roofing Insurance jobs near you
Infographic showing various Roofing Insurance job openings in Chicago, IL as of August 2026, with employment types broken down into 78% Full Time, and 22% Contract. Highlights an 100% In-person job distribution, with an average salary of $81,702 per year, or $39.3 per hour.

Roofing Service Tech

Simon Roofing

Gary, IN • On-site

$23 - $29/hr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 11 days ago

Job description

Roofing Service Technician
We are looking for a Roofing Service Technician to join our organization. If you are a person with a strong work ethic, and basic knowledge of construction or roofing who wants to become a commercial roofing professional and join our team.
We will provide extensive paid training for you to be able make repairs and/or repair recommendations, perform evaluations and Roofing Preventative Maintenance to low slope roofing systems.
You must be professional, presentable, and a good communicator as you will be dealing directly with clients daily.
  • Excellent earnings - $23.00- $29.00 per hour (pay is based on experience; on average our Service Technicians make $77,000+ per year).
  • Forty & more hours per week (with overtime work and pay of 10-15 hours per week).
  • Three (3) annual bonus opportunities (safety bonus of up to $1,500.00 per year, individual performance bonus & company bottom-line bonus).
  • GREAT BENEFITS- Paid Time Off, Health Insurance, Dental, Vision Care benefits, Free life insurance policy, and 401K plan.
  • Opportunity to advance, learn, grow, and increase your earning potential.
  • Training available for experienced construction candidates.
  • A military-friendly and veteran-friendly employer.
What you'll do:
  • Always follow safety on the job and while driving.
  • Inspect problem roofs, perform roof repair, and preventative maintenance.
  • Communication: Speaks clearly and persuasively in positive or negative situations; listens and gets clarification; responds well to questions.
  • Dependability: Completes tasks on time; Follows instructions, responds to management direction.
  • Drives a company vehicle to clients' buildings daily.

What you'll need:
  • Minimum 1 year of relevant roofing or construction experience, or military experience.
  • Driver's License (REQUIRED).
  • 21 years of age or older (REQUIRED to drive company vehicle).
  • High school diploma, or equivalent (REQUIRED).
  • Ability to travel out of town, for up to 4 weeks at a time, when local work is not available (REQUIRED).
  • Must be able to work overtime in emergency situations.
  • Weekend work as needed.
  • Ability to communicate effectively through written correspondence and verbally in English.

Physical Working Conditions:
  • Must be able to lift up to 50 pounds at a time on a regular basis throughout the day.
  • Must be able to frequently ascend/descend ladder from 10 to 40' in height.
  • Must be able to remain in a stationary position for an extended period of time.
  • Constantly works in outdoor weather conditions.
  • Must be able to work in varied extreme weather conditions (extreme hot and extreme cold weather).
  • Load and unload material and equipment and materials from variant heights.
  • Shovel loose materials such as gravel, sand metal snow, or dirt.

Simon Roofing is an Equal Opportunity Employer and does not discriminate against any applicant on race, color, religion, national origin, gender, marital status, age, disability, sexual orientation, military/veteran status, or any other status protected by the Federal or State law or local ordinance.
Note: The statements herein are intended to describe the general nature and levels of work performed by employees, but are not a complete list of responsibilities, duties, and skills required of the personnel so classified. Furthermore, they do not establish a contract for employment and are subject to change at the discretion of the employer.
FL License Number: CCC048202
I certify the information I have provided in this Employment Application is true and complete to the best of my knowledge. I understand that, if hired, discovery of any false information provided or any relevant information omitted (no matter when discovered) may result in the immediate termination of my employment. I authorize Simon Roofing and Sheet Metal Corp. (the "Company") to make whatever inquiries it deems necessary or appropriate of any person or organization to verify any of the information I have provided in this application and to determine my qualifications and abilities. I hereby release the Company from any and all claims or action or causes of action arising out of the Company's lawful inquiries and/or its determination of my qualifications and abilities.

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