Independent Contractor Senior Risk Manager Jobs in Chicago, IL

City Wide Facility Solutions is the largest management company in the building maintenance industry. We secure and manage commercial contracts and partner with skilled independent contractors to perform the work. We handle the sales, client communication, billing, and collections - so you can focus on doing what you do best.

We are selectively partnering with established Independent Contractors and service companies to service our commercial clients in the region. If you operate a structured business, deliver professional facility maintenance, restoration, or renovation services, and are looking for steady, recurring work - without the burden of chasing new contracts or managing collections - this may be a strong fit.

City Wide helps you grow your revenue, keep your crews busy, and get paid consistently - including guaranteed payment on the 10th for work performed.

We operate throughout South Chicagoland and Northwest Indiana - a strong commercial market with warehouses, medical facilities, manufacturing sites, schools, and municipal buildings.

For more information, contact Sandra Rivas at 708-365-8535 or chicagoshores-ic@gocitywide.com.

Requirements

We are selectively partnering with contractors who meet the following:

• Proven experience in commercial roofing (required)
• Proper licensing for commercial roofing work (as applicable)
• General liability insurance and workers’ compensation coverage
• Ability to assess, quote, and execute projects independently
• Professional-grade equipment and crew
• Strong communication and reliability
• Commitment to safety, quality, and timelines

Preferred:

• Experience working in occupied commercial or medical environments
• Ability to provide clear documentation (photos, reports, scope clarity)

ity Wide Facility Solutions is seeking a qualified commercial roofing contractor to support a current client project within our portfolio.

This is a project-based opportunity with the potential for ongoing work across multiple commercial properties, depending on performance, professionalism, and execution quality.

We manage a large base of commercial clients across office, medical, industrial, and institutional facilities. Our model is built around bringing vetted service providers into well-scoped, professionally managed opportunities—allowing contractors to focus on execution, not sales.

If you are looking to supplement your pipeline with well-defined commercial work and long-term partnership potential, this may be a strong fit.

If this is your company, keep reading.

INDEPENDENT CONTRACTORS MUST PROVIDE THE FOLLOWING:

• Valid Business License (if necessary for the service type)
• Worker's Compensation Insurance
• General Liability Insurance
• Federal EIN #
• Other verifiable business
• 18 years of age minimum
• Favorable background investigation results
• You can not be a sole proprietor

The selected contractor will be responsible for delivering high-quality commercial roofing services, which may include:

• Roof inspections and condition assessments
• Leak detection and repair
• Preventative maintenance
• Partial or full roof replacement (as applicable)
• Flat roof systems (TPO, EPDM, modified bitumen, etc.)
• Proper documentation, reporting, and photo verification

Work will be performed in active commercial environments, requiring professionalism, coordination, and adherence to safety standards.

City Wide will:

• Coordinate with the client
• Define scope and expectations
• Manage communication and administrative flow

You focus on:
???? Executing the work at a high level

Benefits

We help you grow a real business - not just pick up extra work.

• Consistent, Recurring Contracts (No Hunting Required)
  We bring you qualified commercial accounts so you can focus on operations - not cold calling, bidding, or chasing leads.
• Reliable, On-Time Payments
  Eliminate collections headaches. We handle billing and client payment - you get paid consistently and predictably.
• Scale Your Revenue Quickly
  Access multiple accounts across our territory - grow from a small crew to a multi-team operation with steady work.
• Professional Account Management Support
  Our Facility Solutions Managers handle client communication, inspections, and issue resolution - helping you retain accounts and maintain high standards.
• No Sales, No Admin Burden
  We manage contracts, client expectations, and service coordination - freeing you to focus on delivering quality work and building your team.
• 20+ Other Opportunities
  Expand into additional services (floor care, porter services, consumables, specialty cleaning) and increase revenue per account.
• Long-Term Partnership Model
  We are invested in your growth - many of our partners have scaled into six-figure and multi-crew businesses with us.