Roofing Sales Representative; In-Home

$70,000 – $200,000+ | Company Vehicle | Warm Leads | Full Benefits

Join the team homeowners already trust.

For more than 50 years, O'LYN Roofing has built a reputation as one of Massachusetts’ premier roofing companies. With 40,000+ completed projects and one of the strongest brands in the region, we provide our sales team with what most companies can’t: credibility, qualified opportunities, operational support, and a process that works.

This is not a door-to-door sales role.

Our Outside Sales Representatives meet with homeowners through company-generated leads, perform roof evaluations, and guide customers through solutions for roofing, gutters, skylights, ventilation, and related systems. If you are confident in consultative sales and want to build a long-term, high-income career with a respected company, this is the opportunity.

• Qualified company-provided leads
• Strong earning potential with uncapped commissions
• Paid onboarding and professional sales training
• Established brand with decades of homeowner trust
• Full benefits package
• Company vehicle, technology tools, and branded apparel

• 401(k) with employer match
• Profit sharing & performance bonuses
• Company vehicle

• Meet with homeowners for scheduled in-home consultations
• Perform roof and related systems inspections.
• Identify customer needs and recommend appropriate solutions
• Present pricing, financing options, and project scope confidently
• Build trust through a consultative, education-first sales approach
• Manage follow-up and pipeline activity within CRM software
• Coordinate internally with production and operations teams
• Maintain strong communication throughout the customer experience

• 2+ years of outside sales, in-home sales, or consultative sales experience preferred
• Experience in roofing, HVAC, windows, siding, remodeling, construction, or home improvement sales is a plus
• Strong communication and relationship-building skills
• Comfortable discussing pricing and financing options
• Self-motivated, organized, and competitive
• Professional demeanor and strong follow-through
• Coachable and process-driven mindset

• Valid driver’s license with clean driving record
• Ability to pass a background check
• Comfortable climbing ladders and performing roof inspections
• Basic proficiency with smartphones, tablets, and CRM software

Based out of Norwood, MA with appointments throughout Greater Boston, Metro West, and the South Shore.

O'LYN Roofing is an Equal Opportunity Employer. We value diversity and are committed to fostering an inclusive environment for all employees.