Roofing Inspector Jobs in Chicago, IL (NOW HIRING)

Custom Installations has been a trusted residential roofing and exterior contractor since 1969, serving homeowners across Northern Illinois and Southeastern Wisconsin. We are known for our 5-Star Google reputation, high-end craftsmanship, and professional, consultative approach. Our work spans cedar, slate, tile, and architectural roofing systems, including historical restoration, retail replacement, new construction, and insurance restoration. Many of our projects involve sophisticated, high-value homes-where credibility, knowledge, and professionalism matter. We are expanding a targeted marketing initiative focused on aging roofing systems, creating consistent opportunity for experienced sales consultants who understand how to educate homeowners and guide them through thoughtful solutions. The Role This is a consultative, inspection-driven sales role, not a high-pressure or door-to-door position. You will serve as the primary point of contact for homeowners seeking expert roof evaluations and replacement guidance within a defined local territory. Leads come from a mix of inbound opportunities, follow-ups, referrals, and targeted outreach. You'll work with a wide variety of roofing systems-including cedar, slate, tile, and high-end architectural roofs-with commissions on individual jobs often reaching five figures. Important note: Climbing steep or specialty roofs is not a core expectation. Inspections are primarily completed using drone technology and ladder access at eaves and transitions, especially on cedar and slate systems where safety is critical.

Key Responsibilities

• Conduct professional roof assessments
• Drone inspections
• Ladder access at eaves, transitions, and perimeter areas

• Identify roofing systems at or near the end of their useful life and clearly explain:
  • Functional limitations and replacement considerations
  • Repair vs. replacement decision-making
  • Insurance restoration options when applicable
  • Educate homeowners on premium materials, upgrades, and long-term value
  • Present estimates, proposals, and recommendations in a clear, professional manner
  • Manage and develop your assigned territory and prospect pipeline
  • Coordinate with production, administrative, and management teams
  • Build long-term relationships with homeowners and referral partners

Who This Role is For

• Has experience in roofing, exterior construction, or insurance restoration sales
• Is comfortable working with high-end and sophisticated clientele
• Prefers education-based, credibility-driven selling
• Is professional, articulate, and presentable
• Can "talk the talk and walk the walk" in front of discerning homeowners
• Wants long-term income growth, not quick churn

Qualifications

• Prior experience in roofing, construction, or insurance restoration sales preferred
• Strong communication, presentation, and follow-up skills
• Comfortable using technology (CRM, tablet, photo documentation, email)
• Self-motivated with strong time and territory management skills
• Valid driver's license and reliable transportation
• Ability to earn a company vehicle based on performance

What We Offer

• Established brand with 50+ years of market credibility
• Paid training during your first month
• Defined local territory (within ~20 miles of Mundelein)
• Structured marketing and lead support
• Administrative support so you can focus on selling
• Access to premium roofing systems (cedar, slate, tile, architectural)
• Multiple revenue streams: retail, restoration, historical, and new construction
• A professional, experienced team environment-not a churn-and-burn sales operation
• Uncapped commission structure with six-figure earning potential

-OTE $100,000 - $250,000 a year -Paid training during your first month -Multiple revenue streams: retail, restoration, historical, and new construction -Ability to earn company vehicle based on performance Uncapped commission structure with six-figure earning potential At Allstar Services, we're redefining the roofing and home improvement industry with rapid growth and innovation. Backed by Morgan Stanley Capital Partners, we operate a national network of top-performing residential roofing companies, delivering best-in-class solutions to homeowners across the U.S. We're built for momentum and innovation, thriving in a high-energy environment where big moves happen fast. With rapid expansion, evolving projects, and the chance to be part of something scaling at an incredible pace, Allstar Services is where you'll gain valuable experience in a dynamic industry. Visit allstarservicesnow.com to explore our brands and career opportunities. Allstar Services is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other protected characteristic. Allstar Home Services (and it's subsidiaries) is committed to protecting its employees, customers, and others while conducting company business. Employment for this position is contingent upon a valid driver's license, a review of the candidate's motor vehicle record (MVR), and successful completion of a background investigation conducted in accordance with Company policies and applicable laws. The Company may conduct MVR checks prior to hire and periodically thereafter. Eligibility to drive a company vehicle is determined based on these reviews, and an unsatisfactory MVR or background investigation may affect driving privileges, vehicle assignment, or employment eligibility. Offers of employment are contingent upon the results of these checks, and any information obtained will be used for employment purposes as permitted by federal and state law and in accordance with Allstar Home Services' Equal Employment Opportunity Policy. We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.