Outside Sales Representative (Field-Based)

Job Title: Outside Sales Representative (Field-Based)

Headquarters: Waukesha, WI - Flexible Schedule

Service Areas: Waukesha, Milwaukee, Ozaukee, Dane, and surrounding counties

Industry: Roofing & Storm Restoration

Compensation: $70k - $150k (based on experience and performance) Bonuses

Benefits: Health, Dental, and Vision insurance available after qualifying period; flexible schedule; advancement opportunities as the company expands across Wisconsin.

Turn your drive into six figures with one of our well-renowned clients based in Wisconsin, a trusted leader in roofing, siding, gutters, and storm restoration.

We’re hiring Outside Sales Representative (Field-Based) to join a growing team that helps homeowners rebuild after storm damage and improve their homes with confidence. This is a great fit for motivated, competitive, and people-focused professionals looking for a long-term career path with unlimited income potential.

Role Overview:

As an Outside Sales Representative, you’ll meet directly with homeowners, assess storm or exterior damage, and guide clients through the insurance claim and restoration process.

This is a 1099 commission-based position with uncapped earning potential and flexible scheduling - ideal for driven closers ready to build a six-figure income while making a real impact in their community.

Key Responsibilities:

· Meet with homeowners to assess roofing, siding, and gutter needs.

· Guide clients through insurance claim processes and project options.

· Present solutions, negotiate contracts, and close sales.

· Prospect new leads through referrals, door-to-door outreach, and networking.

· Maintain strong client relationships and ensure satisfaction.

· Coordinate with the production team for smooth project delivery.

· Represent the company with professionalism and integrity.

Qualifications:

Required:

· 1–2 years of proven sales experience (construction, roofing, or home improvement preferred).

· Strong communication, presentation, and closing skills.

· Self-motivated and goal-oriented with a strong work ethic.

· Valid driver’s license and reliable transportation.

· Eligible to work in the U.S.

Preferred:

· Experience in insurance restoration, door-to-door, or B2C sales.

· Knowledge of exterior construction materials and processes.

· Familiarity with CRM systems or mobile sales tools.

Compensation & Benefits:

Expected first-year income: $70k - $150k (top performers exceed $150k).

Bonuses: Performance-based incentives and rewards.

Benefits: Health, Dental, and Vision insurance available after qualifying period; flexible schedule; advancement opportunities as the company expands across Wisconsin.

Apply today to start the interview process this week and join a high-performing team making a difference in homeowners’ lives.

Job Type: Full-time

Pay: $70,000.00 - $150,000.00 per year

Benefits:

• Dental insurance
• Flexible schedule
• Health insurance
• Vision insurance

Ability to Relocate:

• Waukesha, WI: Relocate before starting work (Required)

Work Location: In person

Salary : $70,000 - $150,000