1099 Door-to-Door Roof Salesperson. Head to storm-affected areas that we recommend in Maryland and connect with homeowners to offer inspections and insurance-funded roofing/siding replacements, they only pay their deductible at the end of the project! Aggressive commission percentages (average $3,200 per job, entry level salary $150,000). First 3 deals guaranteed in training. Retire with this job!