Subcontractor Manager Jobs in Chicago, IL (NOW HIRING)

• Free uniforms


• Health insurance


• Opportunity for advancement


• Paid time off


• Vision insurance


• Wellness resources


• 401(k)


• 401(k) matching


• Competitive salary


• Dental insurance

When disaster strikes, ServiceMaster DSI will be there to help. As the largest operator of ServiceMaster Restore, ServiceMaster DSI has the experience and resources to help homeowners and business owners recover after a loss. From a kitchen fire to a flash flood, ServiceMaster DSI is your recovery expert. DSI is an amazing place to work, with happy employees that are ready to help families and businesses recover from fire and water damage. We provide state of the art equipment and resources to complete our projects successfully.

We’re looking for a Roofing and Exterior Project Manager. This role is to manage the day-to-day execution of exterior insurance repair projects assigned by the General Manager - Exterior Restoration, including roofing and related exterior scopes. This role is responsible for job-site execution, subcontractor management, estimating support, documentation, and quality control on assigned projects, while ensuring compliance with carrier and TPA requirements and job profitability.

The salary for this position starts at $70,000K-$75,000K annually, depending on experience.

• Manage assigned exterior restoration projects from assignment through completion.


• Ensure adherence to insurance carrier and TPA requirements related to exterior damage evaluation, estimating, and photo documentation.


• Prepare and review exterior estimates, ensuring scope accuracy, pricing integrity, and defensibility.


• Source, vet, and manage subcontractors across exterior trades including roofing, siding, gutters, windows, and related exterior repairs.


• Schedule and monitor subcontractor performance to ensure quality, safety, and timeliness.


• Track job costs on assigned projects and flag margin concerns to the General Manager.


• Serve as the primary day-to-day point of contact for customers on assigned projects.


• Coordinate with internal teams to ensure clean handoffs between interior and exterior scopes of work.


• Maintain documentation and quality control practices per company standards.


• Ensure compliance with all company policies, safety procedures, and applicable local and state regulations.

• High School Diploma or equivalent; (College coursework or degree in Construction Management or a related field preferred).


• Minimum of 3 years of experience in exterior construction, roofing, or insurance restoration.


• Experience managing exterior-only insurance repair projects preferred.


• Valid Driver’s License


• HAAG Certification or equivalent exterior damage evaluation training preferred.


• Working knowledge of insurance carrier and TPA documentation and photo requirements.


• Proficiency with Xactimate or similar estimating software.


• Strong organizational and time-management skills.


• Detail-oriented with a focus on documentation accuracy and compliance.


• Ability to work independently in a lean, fast-moving environment.


• Strong communication skills with customers, subcontractors, and internal stakeholders.


• Ability to analyze job costs and make decisions to protect profitability.


• Ability to manage multiple projects simultaneously.


• Ability to conduct customer and subcontractor discussions professionally.


• Ability to perform basic mathematical calculations and financial reviews.


• Ability to complete required documentation and reporting accurately.

• Ability to lift up to 70 pounds.


• Ability to access roofs and exterior elevations safely.


• Ability to see, hear, and communicate clearly.


• Body position abilities include: Standing, walking, climbing ladders, sitting, crouching.


• Body movement abilities include: Bending, reaching, lifting, carrying, and driving

Working conditions will include job sites in varying weather conditions, including extreme heat and cold, as well as some work performed in office or climate-controlled environments. This position will require travel within the assigned market and physical access to exterior work areas, including roofs.

• We are the nation’s largest ServiceMaster franchise company with 26 locations and growing across US


• The culture! We work together – openly and cross-functionally because it enables us to build relationships, learning together and winning as a team.


• Great Benefits! We offer medical, dental, vision, 401(k) match, along with other supplementary plans. Our PTO package helps you have that work/life balance.


• Restoration industry is growing rapidly and so are we!


• We have year-round work that’s steady and consistent.

If you’re looking for a challenging and fulfilling career, be part of the ServiceMaster DSI family.

DSI Holdings is an Equal Opportunity Employer/Vets Welcome!