Outside Sales Representative

ameriproroofing; Chicago (IL); On-site; USD 120,000 - 250,000; Full time

Benefits offered by this job

Vehicle allowance

Company provided leads

Training & mentorship

Job summary

AmeriPro Roofing is hiring Outside Sales Representatives in the Chicago area. You will be the face of the brand, driving exterior home improvements through direct, door-to-door canvassing. We provide training, a platform, and an uncapped commission structure to reward performance.

Ideal candidates bring 1–2+ years of full-cycle sales experience, CRM proficiency, and a proven track record of closing new business. A valid driver’s license and weekend availability are required.

Qualifications

• 1–2+ years full cycle sales experience.
• Experience using CRM tools (Service Titan, Salesforce, HubSpot, etc.).
• Valid driver’s license with insured vehicle and flexible hours.
• Excellent communication, negotiation, and time management.
• Self-directed, coachable and performance-driven.
• Comfortable with outdoor field work and mobile apps.

Responsibilities

• Generate leads through door-to-door canvassing and networking.
• Convert leads provided by marketing and company sources.
• Conduct exterior inspections and assist homeowners with claims or quotes.
• Present options, discuss insurance claims or retail pricing with financing.
• Build and maintain client relationships to drive referrals.
• Monitor pipeline and report progress to leadership.

Skills

CRM experience

Sales experience

Communication skills

Time management

Microsoft Office 365

Driver's license

Tools

Service Titan

Salesforce

HubSpot

Job description

Ready to build a career without financial ceilings? AmeriPro Roofing, an industry-leading name in exterior home remodeling for over two decades, is immediately hiring Outside Sales Representatives. In this role, you will be the face of our brand, using direct, door-to-door canvassing to connect with local homeowners and guide them through essential exterior improvements. We provide the platform, the training and an uncapped commission structure‑you bring the drive to succeed. This position is tailormade for driven, \"hunter\" mentality sales professionals with a proven track record of chasing and closing new business ORthose who are motivated, willing and eager to learn new skills, this is the perfect launchpad for your sales career!

What sets AmeriPro Roofing apart

• Leading CRM and technology (Service Titan) for transparent pricing, margin visibility, scheduling, and seamless workflows that drive efficiency and accountability.
• Company-provided leads supplementing self-generated pipeline.
• Robust training, field support, and clear advancement paths (mentorship).

Compensation and Benefits

• Pay OTE: $120,000–$250,000 per year, plus incentives.
• Performance Pay + Commission Offset (paymenton sales activities)
• Vehicle allowance(for qualifying vehicles)
• Company Provided Leads (supplement self-generated efforts)
• Training, Mentorship,tools and tech provided

Day in the Life

• Morning: Route planning, review yesterday’s follow-ups, confirm inspections.
• Midday: Door-to-door canvassing and neighborhood networking, perform exterior inspections, assist homeowner in claim process or retail quote. Enter data using our mobile canvass application.
• Afternoon: Door-to-door canvassing, Run scheduled inspections (leads), documentation, estimates in our leading CRM Service Titan.
• Evening: Customer follow-ups, proposal reviews, pipeline updates.

Responsibilities & Activities

• Generate Leads: Identify new clients through door-to-door outreach, networking, and referrals.
• Convert Issued Leads: Marketing will provide various lead types through internal and external channels. Leads are supplemental to your generated efforts.
• Conduct Roof/Exterior Inspections: Assess properties for storm damage and overall exterior diagnosis to identify and establish need, measure project areas, and document the condition of materials.
• Educate Homeowners: Explain and build value in our products and services, our brand, discuss the insurance claims process or retail pricing with financing, ensuring the customer understands their exterior home solution options.
• Build Relationships: Establish and maintain strong client connections to drive satisfaction and generate referrals.
• Monitor Sales Performance: Identify market opportunities, track progress, and share updates with internal team and Branch Sales Leadership
• Solve Problems: Address client concerns to ensure seamless experience from inspection to installation.

Qualifications

• 1-2+ years full cycle sales experience with a proven track record preferred
• 1-2 years’ experience using CRM (Service Titan, Salesforce, HubSpot, etc.) Proficiency with Microsoft Office 365 preferred
• Valid driver's license, reliable and insured vehicle; working availability toincludeevenings/weekends.
• Excellent communication, negotiation, time management and organizational skills
• Self-directed, coachable, resilient and motivated by performance-based compensation
• Comfortable with outdoor field work and using mobile apps, mobile device for photos/notes/lead entries.

Location

North, Northwest, and Western Chicago land suburbs.