Top 7 Roofing Jobs in Saint Mary's County Md

Roofing Sales Representative
Old School Roofing —Saint Leonard, MD
- $80,000 - $200,000 a year
- Contract
- Construction site
- Mid-level
- Residential
- Flexible schedule
Quick Apply
2d
Commercial Restoration Sales Executive
Crosby Roofing & Gutters Augusta LLC —United States
- Full-time
- Research
- Mid-level
- Business development
Quick Apply
10d

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Home Genius Exteriors —Washington, DC
Own tools, equipment, and transportation. Home Genius Exteriors is actively partnering with experienced subcontractor crews for residential exterior projects.
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Leak Repair Subcontractor
Dr. Leaks —Washington, DC
This role is for a Leak Repair Subcontractor, and your primary responsibility will be to provide our full array of leak detection and repair services (water…
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Roofing Sales Representative

Old School Roofing -
Saint Leonard, MD

Quick Apply

Job Details

Contract
$80,000 - $200,000 a year
2 days ago

Benefits

Flexible schedule

Qualifications

Customer communication
Construction sales
Residential construction project management
Construction project management
Estimation for residential construction
Managing projects
Restoration project estimation
Roofing
Closing sales

Full Job Description

Old School Roofing, LLC is looking for one or two highly experienced Roofing Sales Representatives to sell and manage residential roofing projects throughout Maryland.

This is not an entry-level position. We are seeking proven roofing professionals who understand insurance-related restoration work, can close profitable projects, and can manage each job from the initial inspection through final completion.

Compensation

60% of the profit on every project you personally sell and manage
Estimated earning potential of $80,000–$200,000 per year
Commission-based with no base salary
Uncapped earning potential
Transparent profit calculations under a written compensation agreement
Flexible schedule

Actual earnings depend on individual production and completed projects.

Responsibilities

Generate leads and close residential roofing projects
Perform roof and property inspections
Document hail, wind, and storm damage with detailed photographs
Sell insurance-related and retail roofing projects
Attend adjuster inspections as the roofing company’s representative
Understand insurance scopes, ACV, RCV, depreciation, deductibles, and supplemental construction items
Help homeowners understand the contractor’s role without interpreting insurance coverage or acting as a public adjuster
Prepare and present estimates, proposals, and contracts
Coordinate materials, crews, scheduling, and customer communication
Manage projects from the signed agreement through completion
Monitor production and workmanship
Conduct final walkthroughs, collect payments, and complete project closeout

Qualifications

At least 3 years of successful roofing sales experience; 5 or more years preferred
Significant insurance-restoration experience
Proven record of closing profitable roofing projects
Experience managing jobs from sale through completion
Strong roofing, storm-damage, estimating, and job-cost knowledge
Excellent sales, communication, organization, and customer-service skills
Ability to generate business and work independently
Valid driver’s license and reliable transportation
Ability to travel throughout Maryland
Active Maryland MHIC salesperson or contractor license strongly preferred; required before independently soliciting or selling home-improvement work

What We Offer

Highly competitive 60/40 profit split
Established roofing crews and production support
Professional contracts and project documentation
High-resolution drone photography and AI-assisted inspection tools
Professional branding and marketing materials
Opportunity to grow with a family-owned Maryland roofing company

About Old School Roofing

Old School Roofing is a three-generation, family-owned roofing company serving homeowners throughout Maryland. We combine more than 30 years of construction experience with modern inspection technology, detailed documentation, honest communication, and experienced workmanship.

Built the Old School Way. With New Technology.

Licensed Bonded Insured
MHIC #168718

To apply, please submit your résumé and include your years of roofing sales experience, approximate sales volume during the past 12 months, insurance-restoration experience, and current MHIC license status.

Only applicants with substantial roofing sales and project-management experience will be considered.

Pay: $80,000.00 - $200,000.00 per year

Work Location: In person

Quick Apply

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