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Outside Residential Sales Professional

Chesapeake Home Restoration
Gaithersburg, MD Contractor
POSTED ON 8/28/2026
AVAILABLE BEFORE 9/26/2026

Outside Sales Representative – Roofing & Siding

Job Type: Full-time or Part-time | 1099 Independent Contractor
Compensation: 5%–8% Commission, based on experience Paid Training $300/month Gas Allowance
Work Location: On the road / Assigned territories

Job Description

We are seeking an Outside Sales Representative to work directly with homeowners throughout our service area. This position is responsible for generating new business, conducting exterior inspections, presenting roofing and siding solutions, and managing customers through the sales process.

This is a 1099 independent contractor position with 5%–8% commission per sale, with the starting percentage determined by relevant sales and industry experience.

New representatives receive paid training for their first 8 weeks while they learn our sales process and begin building their pipeline. Representatives also receive a $300 monthly gas allowance to help offset the cost of working in the field.

There is no commission cap. This position is best suited for someone who is self-motivated, comfortable working independently, and interested in building a strong pipeline within the exterior remodeling industry.

What You'll Do

  • Develop and generate new business using the prospecting methods and strategies you find most effective
  • Speak with homeowners about roofing, siding, and exterior replacement needs
  • Conduct exterior inspections and document visible damage or areas of concern
  • Identify both insurance-related and retail replacement opportunities
  • Present inspection findings and explain available options to homeowners
  • Obtain required signatures and customer documentation
  • Upload photos, documents, and customer information into company platforms
  • Maintain consistent communication with homeowners throughout the sales process
  • Follow up with leads and manage an active sales pipeline
  • Work toward individual and team production goals

Compensation & Benefits

  • 5%–8% Commission per Sale
  • Starting commission percentage based on relevant experience
  • 8 Weeks of Paid Training while you learn the role and build your initial sales pipeline
  • $300 Monthly Gas Allowance
  • Uncapped Commission
  • Bonus opportunities based on performance
  • Flexible schedule
  • Assigned territories based on current opportunities and storm activity
  • Sales training and ongoing support
  • Company systems and tools for managing leads and customers

What Does the Commission Look Like?

For perspective, on a $20,000 project, your commission would be approximately:

  • 5% — $1,000
  • 6% — $1,200
  • 7% — $1,400
  • 8% — $1,600

There is no cap on commission. Actual earnings will vary based on sales volume, project size, commission rate, and completed business.

What We're Looking For

  • Confident and professional communicator
  • Self-motivated and comfortable working independently
  • Comfortable approaching and speaking with homeowners
  • Comfortable working outdoors and conducting door-to-door outreach
  • Reliable transportation
  • Strong follow-up and organizational skills
  • Willingness to learn and follow company sales processes
  • Previous door-to-door, roofing, home improvement, or outside sales experience preferred
  • MHIC Salesperson License is a plus

Who This Position Is For

This role is a good fit for someone who wants their compensation to be directly tied to their performance and is comfortable generating and managing their own sales pipeline.

We'll give you 8 weeks of paid training to learn the industry, develop your sales skills, and begin building your pipeline before transitioning fully into the commission-based compensation structure.

Experienced outside sales and roofing professionals may qualify for a higher starting commission percentage.

Job Types: Full-time, Part-time
Compensation: 5%–8% commission, experience dependent 8 weeks paid training $300/month gas allowance
Work Location: On the road / Assigned territories

Benefits:


  • Mileage reimbursement
  • Paid training


Experience:


  • Sales: 1 year (Required)


Ability to Commute:


  • Frederick County, MD (Required)


Work Location: On the road

Salary : $45,000 - $120,000

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