Demo

Outside Sales Representative (Roofing)

O'LYN Roofing
Norwood, MA Full Time
POSTED ON 3/24/2026
AVAILABLE BEFORE 4/22/2026

About Us:


O'LYN Roofing is a premier, family-owned roofing solutions provider based in Norwood. With over 50 years in business and more than 40,000 projects completed, we have spent decades building a reputation for elite craftsmanship and reliability. We specialize in high-quality roofing, skylights, and gutter systems, driven by a commitment to customer satisfaction and a supportive team culture.

If you are a high-achieving sales professional looking to join a stable, reputable brand with a massive local footprint, we have a seat for you.


What You Can Expect:


We’ve spent half a century building the trust so you can focus on building the relationship. This is an elite, consultative sales career where your expertise is backed by a lead-heavy operation and a production team that actually delivers on your promises. You aren’t here to reinvent the wheel or build a territory from scratch. You are stepping into a refined, high-performance engine designed to turn your sales talent into a professional practice with uncapped financial rewards.


  • Paid Onboarding & Training: We invest in your success from day one. You will receive comprehensive, paid professional training covering our sales process, product knowledge, and safety protocols to ensure you are fully prepared before your first solo consultation.
  • Earning Potential: $70,000 – $200,000 per year (Commission-based).
  • Qualified Leads: Engage with high-quality, company-provided leads.
  • Operational Support: Your focus is on selling and serving homeowners; our production team handles the project logistics and installation.
  • Full Benefits: Medical, Dental, and Vision insurance.
  • Future Planning: Employer-matched 401(k), profit-sharing, and bonuses.
  • Additional Perks: Company vehicle, branded apparel, and the latest technology for field efficiency.

 

 Key Responsibilities:


  • In-Home Consultations: Meet with homeowners onsite to diagnose needs and recommend tailored roofing, gutter, ice-melt, and ventilation solutions.
  • Inspection & Diagnosis: Safely conduct roof inspections to provide accurate, professional recommendations to customers.
  • Value-Based Selling: Present project scope, pricing, and financing options with confidence.
  • Contract Management: Accurately draft, read, and execute professional service agreements.
  • Pipeline Management: Utilize our CRM to track leads, manage your schedule, and maintain consistent follow-up.


What Success Looks Like:


Top performers at O'LYN Roofing don't just "close deals, they also manage a professional practice. Success in this role means:


  • Process Discipline: Executing the full sales process consistently and without shortcuts.
  • Holding Value: Standing behind our 50-year legacy and premium quality rather than relying on discounting to win.
  • Activity Levels: Maintaining strong daily activity levels and pipeline discipline over time.
  • Continuous Growth: Leveraging coaching and regular feedback to consistently sharpen your sales craft.


The Right Professional for O'LYN:


  • Proven Winners: You have 2 years of success in in-home or consultative sales (e.g., roofing, home services, HVAC, windows, or remodeling).
  • Clear Communicators: You can simplify complex technical information for homeowners and build immediate rapport.
  • Financial Confidence: You are comfortable leading direct conversations about pricing, project investment, and financing solutions.
  • Self-Motivated Sellers: You take full ownership of your results and thrive in a commission-based, performance-driven environment.


Where We May Not Align:


  • Prefer Low Accountability: You struggle with structured sales processes or prefer a desk-based environment.
  • Avoid Direct Conversations: You are uncomfortable discussing money, financing, or pricing directly with clients.
  • Are Physicality-Averse: You are uncomfortable with the physical aspects of the job, such as accessing roofs or prioritizing field safety.


Requirements:


  • License: Valid driver’s license with a clean driving record.
  • Background: Ability to pass a background check.
  • Physical: Willingness to climb roofs for inspections and work in a fast-paced environment.
  • Tech Savvy: Ability to use CRM software, smartphones, and tablets.


How to Apply:

Don’t just find a job, build a career with the best in the business. Click Apply to submit your resume, and let’s discuss your future with O'LYN Roofing.


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

Salary : $70,000 - $200,000

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