Skyline Exteriors & Construction | Chicagoland Area
Estimated Earnings: $80,000–$150,000+ per year
Full-Time | Field-Based Position

Proven Roofing Salespeople Wanted

Skyline Exteriors & Construction is expanding and looking for experienced roofing, siding, gutter, and storm-restoration sales professionals.

This position is for someone who already understands the industry, knows how to connect with homeowners, and is ready to work with a company that has the production capacity and support to get jobs completed.

Chicagoland has experienced significant hail activity, and we have an immediate need for proven representatives. There is plenty of opportunity—the right person simply needs the experience, work ethic, and drive to take advantage of it.

Why Experienced Reps Choose Skyline

• $600 weekly draw plus performance bonuses during training
• Expected annual earnings of $80,000–$150,000+
• Our top representative earned more than $250,000 last year
• Medical, dental, and vision insurance
• Company-provided leads
• Strong opportunity for self-generated business
• Weekly sales contests, bonuses, prizes, and incentives
• Ongoing sales and industry education
• Reliable production and administrative support
• Supportive onboarding and a team-first culture
• Flexible schedule and gym membership
• A strong local reputation and a company that stands behind its work

What You’ll Do

You will meet with homeowners throughout the Chicagoland area, evaluate their exterior needs, and help them understand the insurance-restoration process. You’ll remain involved throughout the project, keeping the customer and production team informed from the initial inspection through completion.

You will also build your own pipeline through referrals, networking, neighborhood outreach, and self-generated opportunities while working the leads Skyline provides.

We’re Looking for Someone Who Has

• Previous roofing, siding, gutter, construction, or storm-restoration sales experience
• The ability to safely set a ladder and walk residential roofs
• Confidence speaking with homeowners and meeting new people
• Strong communication, organization, and follow-through
• The motivation to work independently without constant supervision
• A coachable, accountable, and team-oriented attitude
• A valid driver’s license, reliable vehicle, and smartphone

This is an opportunity for an experienced salesperson who is tired of fighting against delayed builds, weak support, or promises that never become paychecks.

At Skyline, you’ll have the work, resources, and support needed to produce at a high level.

Bring in the business. Help the homeowner. Get the project built. Get paid.

Benefits

• Health insurance
• Dental insurance
• Vision insurance
• Flexible schedule
• Professional development assistance
• Gym membership

Job Type: Full-time
Work Location: In person/field-based
Pay: $80,000–$150,000+ per year

We are a hard-working team with big dreams and a reputation growing by the day! We provide an A+ rated, local, honest, and professional approach to every situation. Integrity is our number one ingredient to success, always making our customers' 100% satisfaction our priority!