Entrylevel Gutter Installer Jobs in Chicago, IL (NOW HIRING)

Benefits:

• Bonus based on performance
• Dental insurance
• Flexible schedule
• Health insurance
• Opportunity for advancement
• Profit sharing
• Training & development

The Brothers that Just Do Gutters - Downers Grove, IL
Position level: entry level to experienced
Compensation: Negotiable base + Commission ($50K-$80K+ realistic first-year earnings based on performance)
Location: Lombard, IL (DuPage County - Western Chicago Suburbs)
Job Type: Full-time
About Us
Brothers that Just Do Gutters is reinventing contractor services in the western Chicago suburbs. We're not your typical home improvement company-we've eliminated the pushy sales tactics and built our reputation on honest consultation and exceptional service. Our customers don't feel "sold to"-they feel guided to the right solution for their home.
We're growing fast and need a driven sales professional to help us expand our presence across DuPage County's 340,000+ households.
The Role
This isn't a desk job. You'll be out in the field building relationships, educating homeowners, and creating partnerships that drive sustainable growth.
Your weeks split between:
50% - Customer Appointments (Pre-scheduled leads)

• Meet homeowners at their properties to assess gutter needs
• Provide consultative recommendations (not pushy pitches)
• Close sales on gutter installations, repairs, guards, and cleaning
• Convert leads generated by corporate marketing, Google Ads, and Meta advertising

50% - Business Development (Self-generated opportunities)

• Door-to-door canvassing in target neighborhoods
• Build referral partnerships with roofers, landscapers, window companies, general contractors
• Network with insurance agents, adjusters, and restoration companies
• Develop relationships with property managers, HOA managers, and commercial facility operators
• Attend local business events and community gatherings

What Makes You Successful Here
Must-Haves:

• Comfortable with door-to-door prospecting-you see it as opportunity, not rejection
• Relationship builder who can turn a roofer, realtor, or property manager into a steady referral source
• Self-starter mentality-you don't need someone looking over your shoulder
• Valid driver's license and reliable transportation (you'll be driving throughout DuPage County daily)
• Comfortable working outdoors and climbing ladders to assess gutter systems

Nice-to-Haves:

• Experience with home improvement or B2C sales (roofing, windows, siding, restoration, HVAC, or similar industries strongly preferred)
• Proven track record of meeting/exceeding sales quotas
• Existing network in the home improvement or real estate industries
• Experience with CRM systems (we use ServiceBridge)
• Knowledge of gutter systems, roofing, or exterior home services

Our Culture & Approach
What we ARE:
Honest consultants who educate customers on the best solution
Relationship-focused-we want customers for life, not just one transaction
Quality-obsessed-we stand behind our work
Growth-oriented-we have ambitious revenue goals and reward those who help us hit them
What we're NOT:
❌ High-pressure, "close at all costs" sales culture
❌ Pushy tactics or misleading customers
❌ Selling products people don't need just to hit a number
But make no mistake: We expect results. You'll have targets, and we need someone assertive and motivated to hit them. The difference? You'll do it by being genuinely helpful, not manipulative.
Compensation & Benefits
Base Salary: Negotiable
Commission Structure: 5-10% tiered monthly commission based on sales volume
Bonus Opportunities:

• Quarterly accelerators for exceeding targets
• Annual $10K "Million Dollar Club" bonus
• Self-generated lead bonuses
• After 3 months, eligible for Health Insurance, 2 weeks PTO

Realistic First-Year Earnings: $50K-$80K+ (top performers exceed $100K)
Other Benefits:

• Gas reimbursement/vehicle allowance
• Company-provided leads (50% of your pipeline)
• Professional development and training
• Opportunity to grow into leadership as we expand

This is a high-value territory: owner-occupied homes, well-maintained properties, and homeowners who invest in quality work.
How to Apply
If you're a relationship-driven sales professional who wants to grow with an ethical, ambitious company, we want to hear from you.
What happens next:

• Phone screening (15 min)
• In-person interview at our Lombard office
• Ride-along with our current sales team

Brothers that Just Do Gutters is an equal opportunity employer
We value diversity and encourage applications from all qualified candidates regardless of race, color, religion, sex, national origin, age, disability, or any other protected status.
Ready to join a growing company that's doing contractor work the right way?
Apply now and let's talk about your future with Brothers that Just Do Gutters.
Keywords for search: home improvement sales, exterior sales, door to door sales, B2C sales, gutter sales, roofing sales, contractor sales, field sales representative, outside sales, commission sales, DuPage County jobs, Naperville jobs, Downers Grove jobs
Compensation: $50,000.00 - $75,000.00 per year
Join Our Team at The Brothers that just do Gutters
The Brothers that just do Gutters is a full-service rain gutter and gutter guard franchise, specializing in the installation, repair, and maintenance of seamless gutters, gutter guards, specialty gutters, and more. With over 100 franchise locations across the United States, we are rapidly growing and continuously seeking driven individuals to join our team.
We are a performance-based company dedicated to providing clear career paths for individuals with goals and aspirations. We fully invest in our team members, believing that creating a comfortable and supportive work environment is key to success.
Don't settle for a fixer-upper career. Join us and build something great.
This franchise is independently owned and operated. The franchisee, not The Brothers that just do Gutters Corporate, is the sole employer for this position: your application goes directly to them, they alone make all hiring decisions, and any employment inquiries should be directed to the franchisee rather than to Corporate.