Careers at RS Five — Build a Career, Not Just a Job

Now Hiring — Greater Chicago

Don't Get a Job.
Build a Career.

RS Five is one of the highest-rated exterior restoration companies in our markets — and we're scaling. We're looking for ambitious, growth-minded people who want in on the ground floor of an elite organization with unlimited upside.

See Open Positions Why RS Five

Top 0.1%Of contractors nationwide by certification

$1K–$2K+Weekly income potential, entry level

ZeroExperience required — we train you

Who We Are

An Elite Team With a Simple Belief

RS Five specializes in roofing, siding, gutters, windows, and complete exterior restoration for residential and commercial property owners across Greater Chicago. Our mission is to guide property owners through what's often a stressful restoration process — whether the project runs through insurance or out of pocket.

Our customers consistently rate us among the best in the industry. But here's the part that matters if you're reading this page: we believe in building each other up internally just as hard as we build for our customers. When one person on this team wins, everyone rises with them.

A+ RatedBBB Accredited

GAF Master EliteCertified Contractor

25+ YearsCombined Experience

"A rising tide raises all ships."

— RS Five Core Belief

Open Positions

Two Ways In. One Direction: Up.

Both roles come with a complete training system. We don't hire résumés — we hire work ethic, communication, and coachability. Everything else, we teach.

Position 01 — Field / Entry Level

Property Opportunity Developer

The front line of RS Five. You find the properties that need us before anyone else does.

Walk assigned neighborhoods strategically — every street is a territory, not a route
Spot homes with exterior damage or aging systems others walk right past
Talk with homeowners professionally and confidently
Educate them on the value of a complimentary property inspection
Book appointments for our Certified Property Consultants — and get paid to do it

You're a Fit If You're

Energetic A people person Self-motivated Coachable Goal-oriented On your feet all day, no problem

$1,000 – $2,000+ / week Income potential + advancement into leadership & consulting

Apply for This Role

Position 02 — Sales / Consulting

Certified Property Consultant

The face of RS Five in the field. You inspect, educate, and close — without ever climbing a ladder.

Conduct drone roof inspections — modern tech, zero rooftop risk
Complete ground-level exterior inspections
Perform interior inspections when damage is present
Educate homeowners on their restoration options
Recommend the right solution and guide the insurance-vs-financing decision

You're a Fit If You're

Professional Excellent communicator Comfortable in homes Coachable Performance-driven Career-minded

Fast Commissions A significant portion earned shortly after the signed agreement — not months later

Apply for This Role

The RS Five Difference

Why Top Performers Choose Us

01 / Safety

No Ladders. No Roofs.

Our consultants never climb a ladder or walk a roof. We use drone technology and modern inspection methods that keep you safe while holding professional inspection standards. Elite results without the risk.

02 / Income

Get Paid Fast

Most restoration companies make salespeople wait months for insurance claims to close before commissions hit. Ours are structured so a significant portion is earned shortly after the signed agreement. Faster income. Real financial stability.

03 / Growth

Trained From Day One

No roofing experience? No sales background? Doesn't matter. Our complete training system teaches you everything you need to win — and top performers advance into leadership and consulting roles.

Your Trajectory

The Ladder You'll Actually Climb

The only ladder at RS Five is the career kind. Here's the path our best people take.

Level 1 Opportunity Developer

Master the fundamentals in the field. Learn to read properties, start conversations, and book inspections.

Level 2 Certified Consultant

Run drone inspections, advise homeowners, and close projects with fast-paying commissions.

Level 3 Team Leadership

Train and lead your own field team. Your income scales with the people you build up.

Level 4 Market Growth

Help RS Five open and own new markets as we scale — with the upside that comes with it.

Start Here

Ready to Rise With Us?

Pick your lane and fill out the short form below. No experience necessary — bring the drive, we'll build the skill. A rising tide raises all ships. Get on board.

Position 01 — Field / Entry Level

Property Opportunity Developer

Earn $1,000–$2,000+ per week finding the properties that need us. We train you from day one.

Position 02 — Sales / Consulting

Certified Property Consultant

Drone inspections, fast-paying commissions, and a real career track. No ladders. No waiting on claims.