Demo

Field Sales Representative –

Windy City construction group
Berwyn, IL Full Time
POSTED ON 1/2/2026
AVAILABLE BEFORE 3/3/2026

Field Sales Representative – (Climber)

Location: Illinois – Territory-Based | Full-Time

Compensation: $68,000 – $115,000 annually (Base Commission)

Position Overview

As an Outside Sales Representative (Climber) at Windy City, you are a key member of our sales force. You will scale roofs to perform thorough inspections, generate leads through door to door marketing, and guide homeowners through the roofing and insurance claim process, resulting in signed inspection agreements. This role combines physical activity with relationship building, offering uncapped earning potential and career growth opportunities.

Role Responsibilities

  • Follow the schedule provided by the Field Sales Manager, focusing on high potential territories
  • Engage in door to door marketing to generate leads and build new customer relationships
  • Perform comprehensive roof inspections to assess condition and identify storm damage
  • Educate homeowners on roofing systems and insurance covered damage
  • Guide clients through the insurance claims initiation process
  • Encourage qualified homeowners to enter into inspection agreements
  • Track daily activity using Sales Rabbit or similar CRM, documenting leads, inspections, and signed agreements
  • Send daily summaries to your Field Sales Manager with leads generated, inspections conducted, and contingency agreements signed.
  • Develop and maintain strong relationships with potential clients through follow ups and effective communication
  • Collaborate closely with Account Managers to ensure smooth handoff from inspection to project initiation

Expectations

  • Represent Windy City with integrity and professionalism at all times
  • Meet or exceed weekly targets and performance metrics
  • Attend scheduled meetings, trainings, and coaching sessions on roofing trends, materials, and best practices
  • Contribute to a positive team environment by collaborating and sharing insights

Qualifications

  • Experience in roofing, sales, or a related field preferred
  • Comfortable working at heights (walking on roofs, climbing ladders)
  • Strong physical stamina and ability to lift materials as needed
  • Excellent communication and customer service skills
  • Familiarity with Sales Rabbit or other CRM tools is a plus
  • Ability to work in various weather conditions
  • Team player with strong work ethic and attention to detail
  • Valid driver's license

Why You'll Love This Job

  • High earning potential: $68,000 – $115,000 annually (Base Commission) – no limits for top performers
  • Career growth into senior sales, management, or account executive roles
  • Autonomy and ownership over your territory
  • Make a real impact by helping homeowners maximize their insurance recoveries
  • Join a top-performing, supportive team with opportunities for advancement

Ready to Join?

If you're a driven, high-energy sales professional looking for a rewarding opportunity with uncapped earning potential, this is your chance. Don't settle for capped commissions—apply now and take control of your income while helping homeowners protect their property.

Job Type: Full-time

Pay: $68, $115,000.00 per year

Work Location: In person

Salary : $68,000 - $115,000

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