We are seeking an experienced Commercial Roofing Estimator to join a highly established, growing commercial roofing and architectural sheet metal contractor in McHenry, Illinois.

This is an opportunity to take ownership of an active commercial bid pipeline and play a meaningful role in the continued growth of a nearly 50-year-old organization with approximately 150 employees and $45 million in annual revenue.

The company operates differently from a traditional roofing contractor. Estimating, project management, drafting, fabrication, and field operations work closely together, supported by an extensive in-house sheet metal fabrication operation and a highly developed production infrastructure.

For the right person, this role offers significant runway. We are open to an experienced estimator who can make an immediate impact, as well as a senior-level industry professional with the leadership ability to help elevate the department and potentially grow into an Estimating Team Lead or department leadership position.

What You’ll Do

You will manage commercial roofing opportunities from initial bid review through final submission and award, then transition awarded projects to the Project Management and Operations teams.

Responsibilities include:

• Review plans, specifications, addenda, alternates, and complete bid packages

• Perform detailed commercial roofing and architectural sheet metal takeoffs and quantity surveys

• Develop comprehensive labor, material, equipment, and subcontractor estimates

• Estimate projects ranging from approximately $150,000 to multimillion-dollar commercial facilities

• Prepare bids for restaurants, national retail and chain locations, schools, airports, institutional facilities, and other large commercial projects

• Manage public-sector and prevailing-wage bid requirements when applicable, including bonds, prequalification documents, required forms, and submission deadlines

• Estimate a variety of roofing systems, including TPO, EPDM, PVC, modified bitumen, built-up roofing, and architectural sheet metal

• Manage RFIs, revisions, addenda, bid documentation, and bid-day submissions

• Maintain an organized and accurate bid calendar while identifying scope, capacity, pricing, and scheduling risks early

• Develop strong relationships with general contractors and customers to help strengthen repeat business and future bid opportunities

• Work closely with Business Development while independently managing the technical estimating and bidding process

• Prepare clear project handoffs, including scope details, exclusions, assumptions, job documentation, and identified risks

• Review completed project costs against original estimates and incorporate lessons learned into future bids

• Contribute ideas that improve estimating processes, accuracy, efficiency, and overall department performance

What We’re Looking For

The ideal candidate is more than someone who can complete a takeoff. We are looking for an estimator who understands the commercial side of the business, takes ownership of their work, communicates confidently, and wants to contribute to the growth of the organization.

Qualifications include:

• 3-5+ years of direct commercial roofing estimating experience preferred

• Demonstrated responsibility for managing complete bids from initial review through submission

• Strong knowledge of commercial roofing systems and installation methods

• Experience estimating projects ranging from six figures into the multimillion-dollar range

• Strong ability to read and interpret plans, specifications, scopes, and construction documents

• Experience developing detailed labor, material, equipment, and subcontractor cost estimates

• Familiarity with public bidding and prevailing-wage projects is strongly preferred

• Proficiency with STACK, The EDGE, Bluebeam, or comparable construction estimating software

• Strong organizational skills and the ability to manage multiple active bids and competing deadlines

• Commercial mindset with the ability to build relationships and represent the company confidently with customers and general contractors

• Collaborative, team-oriented approach with a strong sense of accountability

• Ability to work full-time on-site in McHenry, Illinois

Commercial roofing experience is strongly preferred; however, exceptional estimators from closely related construction disciplines may also be considered depending on their technical background and ability to transition into the roofing industry.

Compensation & Incentives

This position offers a highly competitive compensation structure designed to reward strong individual performance and profitable project wins.

• Base salary: Approximately $90,000–$140,000+, with flexibility for exceptional industry talent

• Commission: Performance-based commission tied to awarded work and project profitability, with payments distributed throughout the project lifecycle

• Additional performance bonuses: Available based on annual sales and production milestones

• Benefits: Comprehensive benefits package, with the company covering approximately 75% of employee premium costs

• Additional industry perks and opportunities, including manufacturer and supplier-sponsored trips

Why Join?

This is a chance to join an established company with nearly five decades of industry experience while becoming part of its next phase of growth.

The organization has built an exceptional production operation with capabilities that are difficult to replicate in the commercial roofing market. Its McHenry campus brings together estimating, project management, drafting, fabrication, and operations, including an approximately 40,000-square-foot sheet metal fabrication operation within a roughly 100,000-square-foot facility.

The company is investing in growth, business development, and the next generation of leadership across its markets, with opportunities extending beyond Chicago into New York and Florida.

For someone with ambition, technical expertise, and leadership potential, there is a clear opportunity to advance quickly, help shape the estimating department, and play a significant role in the company's continued expansion.

If you are an experienced commercial roofing estimator who wants more ownership, stronger earning potential, and the opportunity to grow with an established industry leader, we want to hear from you.