Exterior Remodeling Outside Sales Representative - Roofing, Windows, Doors, Siding, and Gutters

Job Title

Residential Exterior Sales Representative (1099 Independent Contractor)

Company

Chesapeake Roofing, Windows & Siding – Davidsonville, MD

Job Type

1099 Independent Contractor – Commission Only – Flexible / Seasonal-Friendly

Overview

Join Chesapeake Roofing, Windows & Siding as an Outside Sales Representative and build a high-income career in residential exterior remodeling. You’ll be the frontline ambassador for our premium roofing, siding, window, and door solutions, meeting with homeowners, assessing their needs, and delivering tailored proposals that solve real problems and enhance curb appeal. This role is ideal for a motivated closer who wants control over their schedule, uncapped commission potential, and the opportunity to grow with an established local brand serving Anne Arundel, Howard, Prince George’s, and surrounding counties.

What You’ll Do

• Schedule and run qualified company-provided leads and in‑home appointments with residential homeowners.
• Self‑generate additional leads through networking, referrals, and canvassing to earn higher commission margins.
• Perform thorough exterior inspections for roofing, siding, windows, doors, and gutters; identify issues and recommend appropriate solutions.
• Use our company quoting system on a provided laptop to build accurate, professional proposals and close deals in the home.
• Follow up promptly with all assigned leads, calls, emails, and texts to maximize close rates and deliver a great customer experience.
• Maintain organized notes, measurements, photos, and job details inside our systems for smooth handoff to production.
• Represent Chesapeake Roofing, Windows & Siding professionally in branded apparel at all appointments and neighborhood visits.
• Attend occasional sales meetings and training sessions to stay sharp on product knowledge, pricing, and processes.

Products You’ll Sell

You’ll primarily sell high‑quality, name‑brand products homeowners already recognize and trust, including:

• Roofing: CertainTeed, GAF
• Siding: CertainTeed, Mastic, James Hardie
• Gutters/Gutter Guards: Spectra, Leaf Solutions Xtreme, & Bulldog
• Windows & Doors: ProVia, Simonton, Andersen, Harvey, Wincore, Pella

Experience with these or similar lines is a strong plus.

Ideal Candidate

• 3 years of successful in‑home residential sales selling exterior home improvements such as roofing, siding, windows, doors, and gutters.
• Comfortable running 100% commission and motivated by uncapped earnings.
• Technically savvy: confident using a laptop, CRM/quoting tools, email, and digital measurements/photos.
• Strong closer with solid communication, in‑home presentation, and objection‑handling skills.
• Organized and responsive with strong follow‑through on all assigned leads.
• Reliable vehicle, valid driver’s license, and personal smartphone (you cover your own gas and phone).
• Comfortable working across Anne Arundel, Howard, Prince George’s, and nearby counties.
• Able to work a flexible schedule including some evenings and Saturdays during peak season, with the option to scale back during slower winter months if desired.

Compensation & Structure

• 1099 independent contractor (not a W‑2 employee).
• Commission‑only pay with uncapped earning potential; higher commission percentages for self‑generated jobs.
• On‑Target Earnings: $125,000 –$175,000 per year, commission only.
• Exclusive role: concurrent work with competing roofing, window, siding, or exterior remodeling companies is not permitted.
• Company‑provided: pre‑qualified leads, company laptop for quoting and presentations, company‑branded apparel
• You are responsible for your own vehicle, fuel, insurance, and phone.

About Chesapeake Roofing, Windows & Siding

Chesapeake Roofing, Windows & Siding is a locally family- owned exterior remodeling company based in Davidsonville, MD, proudly serving homeowners throughout Anne Arundel, Howard, Prince George’s, and surrounding counties since 1987. We focus on high‑quality installations, premium materials, and a straightforward, no‑games sales process that earns referrals and repeat business. If you’re a hungry closer who wants autonomy, a strong brand behind you, and a proven product mix, we’d like to talk.

How to Apply

• Apply through Indeed with your resume highlighting:
• Your residential exterior/home‑improvement sales experience
• Product lines you’ve sold (roofing, siding, windows, doors, gutters)
• Your average annual sales volume and close rates
• At least two professional references (ideally direct managers or owners in residential construction or home-improvement sales), including names, phone numbers, and relationship
• Shortlisted candidates will be contacted to schedule an interview.

Pay: $50,000.00 - $250,000.00 per year

Work Location: Hybrid remote in Annapolis, MD 21401

Salary : $50,000 - $250,000