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Property Insurance Jobs in Chicago, IL (NOW HIRING)

Our Property Team is looking for a property underwriter with recognized experience and visibility in the Commercial Property insurance market and a successful track record in underwriting both global ...

Our Property Team is looking for a property underwriter with recognized experience and visibility in the Commercial Property insurance market and a successful track record in underwriting both global ...

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Senior Broker, Large Property

Chicago, IL · Hybrid

$145K - $185K/yr

Lead broker on complex insurance programs - Perform strategic assessment, design solutions and ... As a Senior Large Property Broker at Aon, you'll be empowered to lead major placements, influence ...

Merlin Law Group is a national insurance claim litigation firm that handles commercial property insurance claims, residential property insurance claims and bad faith claims. We are dedicated to ...

Attorney of Counsel

Chicago, IL · On-site

$160K - $200K/yr

The successful candidate will have an established understanding of first-party insurance coverage, with an emphasis on property insurance; * Regularly conduct 30(b)(6) depositions, as well as the ...

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Property Insurance information

See Chicago, IL salary details

$14

$37

$70

How much do property insurance jobs pay per hour?

As of Aug 1, 2026, the average hourly pay for property insurance in Chicago, IL is $37.46, according to ZipRecruiter salary data. Most workers in this role earn between $26.49 and $45.05 per hour, depending on experience, location, and employer.

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

Professionals in property insurance often encounter challenges such as accurately assessing property risks, staying updated on changing regulations, and managing claims during catastrophic events. To address these, it's important to continuously update your knowledge through ongoing training, maintain strong communication with clients and underwriters, and utilize modern technology for risk assessment and claims processing. Building strong relationships with colleagues in underwriting, claims, and risk management teams also helps in efficiently resolving complex cases.

What is the difference between Property Insurance vs Property Claims Adjuster?

AspectProperty InsuranceProperty Claims Adjuster
RoleInsurance policy provider that offers coverage for property damage or lossProfessional who assesses and processes claims related to property damage
CredentialsInsurance license, knowledge of policies and coverageAdjuster license, understanding of claims and damage assessment
Work EnvironmentInsurance companies, offices, onlineOn-site inspections, fieldwork, claims offices
Industry UsageInsurance providers, brokersInsurance companies, independent adjusting firms

Property Insurance involves providing coverage for property damage, while Property Claims Adjusters evaluate and settle claims after damage occurs. Both roles require knowledge of policies and damage assessment, but one focuses on policy provision and the other on claims processing.

What are the key skills and qualifications needed to thrive as a Property Insurance Agent, and why are they important?

To succeed as a Property Insurance Agent, you need a strong understanding of insurance policies, risk assessment, and regulatory compliance, typically supported by a relevant license. Familiarity with insurance management software, quoting systems, and CRM platforms is essential. Excellent interpersonal skills, attention to detail, and problem-solving abilities set top performers apart in this role. These skills and qualifications are crucial for building client trust, ensuring accurate policy management, and providing effective risk solutions.

What is property insurance?

Property insurance is a type of coverage that protects individuals or businesses against financial loss due to damage or theft of physical property, such as homes, buildings, or personal belongings. It typically covers losses caused by events like fire, theft, vandalism, and certain natural disasters, depending on the policy. Property insurance can include different types of policies, such as homeowners insurance, renters insurance, and commercial property insurance. Having property insurance helps ensure that you are financially protected if unexpected damage or loss occurs.
Infographic showing various Property Insurance job openings in Chicago, IL as of July 2026, with employment types broken down into 1% As Needed, 73% Full Time, 21% Part Time, and 5% Contract. Highlights an 95% Physical, 2% Hybrid, and 3% Remote job distribution, with an average salary of $77,924 per year, or $37.5 per hour.

Senior Regional Retail Property Manager

Curbline Properties

Chicago, IL

$98K - $122K/yr

Other

Posted 18 days ago


Job description

Description

The Property Management team at Curbline Properties is seeking a Senior Regional Retail Property Manager to lead the strategic oversight, operational performance, and financial management of a portfolio of convenience retail properties throughout the Midwest. This role is responsible for driving operational excellence, building strong tenant relationships, managing budgets and financial goals, and maximizing the value of a growing retail real estate portfolio. The position serves as the primary liaison between ownership, tenants, vendors, and internal stakeholders while leading a regional property management team across multiple locations. The ideal candidate is a results-driven property management professional with deep experience overseeing retail assets and a proven ability to lead a regional team.


The position is based remotely in Chicago, IL; Indianapolis, IN; or Minneapolis, MN, with regular travel (approximately 50%-70%) to assigned retail properties and construction sites for on-site monitoring and meetings. Occasional extended hours may be required during peak periods.  The role includes work in outdoor and construction environments, which may involve exposure to weather conditions, noise, and dust.


The expected salary range for this full-time salaried exempt position is between $98,000-$122,000. Actual compensation will be based on factors such as scope and responsibilities of the position, candidate's work experience, education/training, job-related skills, internal peer equity, geographical and industry market data, and business considerations and other factors permitted by law.


To be successful in this role, you will need to:


Property Operations

Oversee day-to-day operations of a regional portfolio of convenience retail assets.

Ensure properties are maintained in compliance with company standards, local regulations, and lease requirements.

Conduct regular property inspections and implement corrective action plans as needed.

Develop and execute operational strategies that enhance asset performance and tenant satisfaction.


Financial Management

Prepare, manage, and monitor annual operating and capital budgets.

Review monthly financial statements, variance reports, and operating results.

Identify opportunities to increase revenue and reduce operating expenses.

Approve invoices, contracts, and purchase orders in accordance with company policies.

Support annual budget planning, forecasting, and reforecasting processes.


Tenant Relations

Maintain strong relationships with retailers, tenants, and key stakeholders.

Ensure tenant compliance with lease obligations.

Coordinate tenant move-ins.

Partner with leasing teams to support occupancy goals and tenant retention initiatives.

Resolve tenant concerns promptly and professionally.


Vendor and Contract Management

Oversee procurement and management of third-party service providers.

Negotiate service agreements and monitor vendor performance.

Ensure contractors meet insurance, safety, and contractual requirements.

Drive cost-effective service delivery while maintaining quality standards.


Capital Projects & Maintenance

Manage capital improvement and property enhancement projects.

Coordinate with construction, facilities, and asset management teams on project execution.

Monitor project budgets, schedules, and quality outcomes.

Ensure preventative maintenance programs are effectively implemented.


Risk Management & Compliance

Ensure compliance with all applicable local, state, and federal regulations.

Maintain property records, permits, licenses, and inspection documentation.

Lead risk management initiatives and emergency response planning.

Monitor life-safety systems and property insurance requirements.


Leadership & Team Management

Lead, mentor, and develop Regional Property Managers, Property Managers, and support staff.

Establish performance goals and conduct employee evaluations.

Promote a culture of accountability, collaboration, and customer service excellence.

Support recruitment, onboarding, and professional development efforts.


Asset Performance

Collaborate with Asset Management, Leasing, Accounting, and Development teams to maximize property value.

Analyze operational and financial performance metrics.

Provide recommendations for strategic improvements and value-enhancing initiatives.

Participate in quarterly Portfolio Reviews.


ABOUT US

Curbline Properties' is the first publicly traded REIT (NYSE: CURB) focused exclusively on owning and managing convenience shopping centers positioned on the curbline of well-trafficked intersections and major vehicular corridors in suburban, high household income communities. We operate as a distinct sector within the retail real estate landscape. We are headquartered outside of Cleveland in Beachwood, Ohio, and have regional offices in New York City, Atlanta, Georgia and Boca Raton, Florida.Â