Outside Sales Representative - Chicago

Confidential

Crystal Lake, Illinois permanent

Posted: March 12, 2026

Quick Summary

We're looking for an Outside Sales Representative to join our team in Chicago, Illinois. As a successful Outside Sales Representative, you'll be responsible for generating company leads and building relationships with customers. With a 40-year established company with a strong brand, this is a fantastic opportunity to join the St. Louis branch.

Job Description

40 year residential/commercial roofing company looking for sales reps for D2D + company leads in Chicago.

W-2, health insurance, company truck and gas, 401k, laptop, CRM, commercial estimators and internal supplementing support, would entertain you producing your own jobs, if experienced enough, but I would rather you focus on sales

There is High Earning Potential with this position!

Why Join Messing Roofing?

40-year established company with strong brand credibility

Ground-floor opportunity to help build the St. Louis branch

Many company-generated leads

Full estimating, production & administrative support

Commission-based compensation – NO CAP

$150,000 – $250,000+ realistic earning potential

Performance bonuses & incentives

Clear promotion and leadership opportunities as the branch grows

Company truck provided

Gas card provided

Company laptop provided

Company cell phone provided

Health, Dental & Vision Insurance

401(k) Retirement Plan

What You’ll Do

Perform thorough roof and siding inspections

Identify storm-related and age-related damage

Generate additional opportunities through canvassing and referrals

Educate homeowners on roofing systems and restoration options

Guide clients through the insurance claims process

Work directly with adjusters to ensure proper coverage

Present detailed and competitive estimates

Use a consultative selling approach to build trust and close business

Maintain strong communication from contract through project completion

Who We’re Looking For

Proven roofing sales, storm restoration, or insurance claims experience preferred

Strong consultative selling and closing skills

Self-motivated and disciplined

Comfortable climbing roofs and performing inspections

Valid driver’s license

Flexible schedule, including evenings and weekends

Key Traits

Professional presence

High integrity and strong character

Competitive but customer-focused

Ambitious and growth-oriented

Not afraid of heights

Physical Requirements

Remove and set up ladders from service trucks

Safely access and walk residential roofs

Lift and carry up to 50 lbs regularly

Stand for extended periods

Bend, kneel, crouch, and perform repetitive movements

Compensation

This is a commission-based position with no cap on earnings.

Experienced, driven consultants realistically earn $120,000 – $250,000+ annually, with top performers exceeding that range.

Your income is directly tied to your performance — and there is no ceiling.

We’re building something big in St. Louis. The right professionals won’t just sell — they’ll help shape the future of this branch and grow into leadership roles as we expand.

If you’re ready to earn at a high level, receive full benefits including 401(k), and be part of something growing — apply today.

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