Commercial Roofing Senior Estimator

Location: Northwest Chicago Suburbs, IL

Territory: Chicagoland, Southern Wisconsin & Northwest Indiana

Compensation: $95K–$115K Base + Commission + Company Vehicle/Gas

Job Type: Full-Time

Industry: Commercial Roofing

A growing commercial roofing contractor in the Northwest Chicago suburbs is looking for an experienced Commercial Roofing Sales Estimator who can take a reroofing opportunity from the initial roof inspection through estimating, proposal and close.

This is not a desk-only estimating position
.

We're looking for someone who knows commercial roofing, is comfortable operating independently in the field and can sell the work they estimate. You should be equally comfortable meeting with a customer, climbing a roof, taking measurements and core samples, building an estimate and presenting the solution to the client.

• Develop and manage commercial reroofing opportunities
• Meet directly with building owners, property managers and commercial customers
• Travel to customer locations and jobsites throughout Chicagoland, Southern Wisconsin and Northwest Indiana
• Perform roof inspections and assess existing roof conditions
• Complete field measurements, takeoffs and core samples
• Identify appropriate reroofing systems and project scopes
• Prepare your own estimates from field information
• Enter estimates, project information and customer activity into company software
• Prepare and present proposals
• Follow opportunities from initial inspection through close
• Build long‑term relationships with customers and generate repeat business
• Maintain an active sales pipeline using Salesforce
• Work closely with operations once projects are sold

• Strong commercial roofing experience, particularly reroofing and roof replacement
• Proven ability to sell commercial roofing projects
• Able to independently inspect and evaluate an existing commercial roof
• Experience completing field measurements, takeoffs and core samples
• Able to develop project scope and build your own estimate
• Comfortable working independently and operating from a company pickup truck
• Strong customer‑facing and relationship‑building skills
• Comfortable presenting proposals and asking for the business
• Experience using Salesforce or another CRM
• EDGE estimating experience is an asset
• Knowledge of commercial roofing systems including TPO, EPDM, PVC, modified bitumen and related systems
• Strong understanding of commercial roofing pricing, labor, materials and project requirements
• Valid driver's license and ability to travel throughout the territory

• $95K–$115K base salary, depending on experience
• Commission opportunity based on sales performance
• Company vehicle/pickup truck
• Gas expenses covered
• Health insurance
• Paid time off
• Opportunity for increased earnings as the territory and customer base grow

The ideal candidate is someone who has spent time in the commercial roofing industry and understands the entire reroofing sales process.

You don't need an office to tell you how to scope the project. You can take the company truck to the property, meet the customer, get on the roof, determine what you're looking at, take cores and measurements, develop the scope, put together your estimate and then sell the job
.

We're looking for someone who combines the technical knowledge of an estimator with the drive and customer skills of a salesperson.

This is an opportunity to join an established commercial roofing contractor that is continuing to grow throughout the region.

You’ll have the independence to manage your own opportunities while being backed by an experienced roofing operations team.

If you're an experienced commercial roofing professional who knows how to inspect it, estimate it and sell it
, we'd like to hear from you.