Job Description

Location: Chicago-area field/hybrid role serving McHenry County, the greater Chicago metro, and Southern Wisconsin

Compensation: $90,000–$130,000 base + uncapped commission

Reports To: Director of Estimating

Employment Type: Full-Time

The Opportunity

Starts Align is recruiting an experienced Outside Sales Representative – Commercial Roofing on behalf of an established, full-service commercial roofing and building-envelope contractor serving the greater Chicago market and Southern Wisconsin.

This is a true business development and field sales role for a commercial roofing professional who knows how to create opportunities, build relationships with decision-makers, assess roofing needs, price standard replacement projects, and ultimately close profitable work.

The ideal candidate is a self-starter with an established understanding of the commercial roofing market who is comfortable owning the entire sales cycle—from prospecting and roof inspection through proposal, negotiation, and signed contract.

While an experienced estimating team is available to support larger or more complex opportunities, this position is designed for someone who can generate their own pipeline and move business forward independently rather than relying solely on company-provided leads.

The company offers commercial roofing, architectural sheet metal, ACM, fabrication, and service capabilities under one organization, allowing the sales team to bring comprehensive solutions to customers and seamlessly transition awarded projects to experienced estimating, project management, and operations teams.

Key Responsibilities

• Generate new commercial roofing opportunities through direct prospecting, referrals, existing relationships, networking, and field activity.
• Build, manage, and grow an owner-direct sales pipeline throughout McHenry County, the Chicago metro, and Southern Wisconsin.
• Develop relationships with building owners, property managers, facility directors, portfolio managers, general contractors, and other key decision-makers.
• Conduct site visits and roof inspections to evaluate existing conditions and identify project scope, materials, labor considerations, and scheduling requirements.
• Develop competitive quotes and proposals for standard commercial roof replacement and re-roofing projects.
• Partner with estimating and operations teams on larger, more technical, or complex opportunities.
• Present proposals, respond to RFQs and RFPs, negotiate terms, overcome objections, and close profitable commercial work.
• Maintain consistent follow-up throughout the sales cycle and develop long-term customer relationships that generate repeat business.
• Provide estimating, project management, and operations teams with accurate, clearly defined project scopes upon award.
• Attend pre-bid meetings, job meetings, and customer meetings as needed.
• Monitor competitive and market activity and communicate relevant intelligence internally.

Qualifications

• 5–10 years of commercial roofing sales experience, or commercial roofing estimating experience combined with a demonstrated track record of successful sales.
• Proven ability to self-generate B2B opportunities, build a pipeline, access decision-makers, and close new business.
• Strong working knowledge of commercial roofing systems, including TPO, EPDM, PVC, modified bitumen, built-up roofing, and metal roofing systems.
• Steep-slope roofing experience is a plus.
• Ability to read and interpret roof plans, specifications, drawings, and construction documents.
• Sufficient estimating knowledge to independently develop pricing for standard roof replacement projects and recognize when additional estimating or operational support is needed.
• Strong communication, relationship-building, presentation, and negotiation skills.
• Highly self-motivated with the ability to manage a territory and sales pipeline independently.
• Valid driver’s license and ability to safely access and inspect commercial rooftops in seasonal weather conditions.
• Ability to regularly travel throughout McHenry County, the greater Chicago area, and Southern Wisconsin.

Existing relationships within the commercial roofing, property management, facilities, construction, or building-owner community are highly valued; however, candidates must also demonstrate the ability to independently create and develop new business.

Compensation & Benefits

• $90,000–$130,000 base salary, depending on experience.
• Uncapped commission under the company's sales commission plan.
• Seven paid company holidays.
• Medical, dental, and vision coverage for employees and their families beginning after 90 days of employment, with the company currently covering 75% of the premium.
• 401(k) with company match of up to 4% beginning after six months of employment.
• One week of vacation beginning after 60 days of employment.
• One week of paid leave beginning after 90 days of employment.
• Additional compensation and benefits are subject to applicable company policies and written plan terms.

This is an excellent opportunity for a commercial roofing sales professional who wants the autonomy to build and own a territory, earn uncapped commission, and sell the capabilities of a well-established full-service contractor with the operational resources to execute the work they bring in.