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Old School Roofing
Roofing Sales Representative
Career Insights for Estimator
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Based on Maryland data
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What they do
An Estimator provides cost estimates for a project, based on an evaluation of the materials, labor, time and equipment needed to complete the project. May specialize in many aspects of construction or in manufacturing and design industries.
$75,967 / year median in Maryland
+3% projected growth
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.