Roofing Sales Representative / Business Development

Join Dad Exteriors as a Roofing Sales Representative / Business Development professional in Chicago, IL (hybrid). This full-time, field-based role combines company-generated leads with your own prospecting, giving you a clear path to build pipeline and earn at a high level.

You will work in a founder-led organization where performance is noticed and rewarded. Dad Exteriors also provides sales tools, estimating support, and production coordination, so you can focus on consultation, proposals, and closing while ensuring a smooth handoff to the production team.

Compensation & opportunity

• Competitive base plus uncapped commission, based on experience and results
• Pay range: $48,000.00 - $250,000.00 per year
• Company-generated opportunities alongside your own outreach efforts
• Growth path toward sales leadership as the business expands

What you’ll do

• Prospect and generate new roofing opportunities throughout Chicago
• Build relationships with homeowners, real estate professionals, property managers, and referral partners
• Conduct initial customer consultations to identify roofing needs
• Present estimates and proposals, overcome objections, and close deals
• Follow up consistently with prospects and existing customers
• Develop referral business and support long-term customer relationships
• Manage opportunities and the sales pipeline in CRM
• Coordinate with the production team to ensure a smooth customer handoff
• Represent Dad Exteriors with professionalism, confidence, and integrity

What you bring

• Proven sales experience, preferably in roofing, windows, siding, construction, or home improvement
• Self-starter mindset and comfort with running your day without constant direction
• Comfortable prospecting through cold calling, networking, and generating your own leads
• Excellent communication and relationship-building skills
• Confidence presenting and closing high-ticket projects
• Strong organization and accountability, with comfort using CRM software
• Valid driver’s license and reliable transportation
• Focus on customer experience beyond just obtaining signatures
• Drive to build your own pipeline with discipline to follow through

Location & work setup

• Job type: Full-time
• Location: Chicago, IL (Field-Based)
• Work location: Hybrid remote in Chicago, IL 60639

How to apply

Submit your resume and briefly answer these three questions:

• What have you sold, and what were your approximate annual sales results?
• How do you generate new business when the company isn’t providing leads?
• Why do you think you’d be successful selling roofing in Chicago?