Earn what you're worth.
Build the life you want.
1 million Chicagoland roofs need replacing after recent storms. We're looking for sales reps who want to grow a rewarding career helping homeowners navigate the insurance claim process to get their new roof covered. Paid training, hands-on mentorship, and a comp plan that rewards your effort with no ceiling on what you can earn.
Paid weekly while you learn. Paid more once you produce.
Most D2D roofing offers are commission-only from day one — which is fine if you've already got a pipeline, but rough if you don't. We pay you weekly during a 12-week ramp so you can focus on getting good without watching your bank account empty.
A comp plan that rewards your effort.
You'll earn 5% of the contract value on every deal you set, from your first week onward. Once you're trained to run the full sales process (inspection, presentation, and closing), you'll earn an additional 5% on every deal you close yourself — for a total of 10% on revenue you originate. The more you sell, the more you make, with no cap on your earning potential.
This is a probability game, not a sales game.
Real numbers from our team. We're showing you the activity-to-paycheck math up front so you can decide whether the offer works for you before you spend a minute in the field.
| Step (full-time D2D, post-training) | Volume |
|---|---|
| Doors knocked / week5 days × 6 hrs of knocking × ~12 doors/hr | ~360 |
| Doors that open & talk~30% answer rate when the storm is fresh | ~108 |
| Inspections set / weekFace-to-face beats the phone every time | ~7 |
| Deals that stickInspected, signed, claim approved, deposit collected | ~3 |
| Avg contractPremium product mix moves this number up | $24,000 |
| Weekly revenue you generated | ~$72,000 |
| Commission at 10%5% for setting + 5% for closing the deal yourself | ~$7,200 |
You knock. You set. You learn to close. Then you close.
Field role in the Chicagoland storm zones. Full-time, 1099 contractor, paid every Friday. Closer trainees ride with our existing closers (Austin and Marco) until they can run the kitchen-table presentation themselves.
Spring Grove ↔ Belvidere corridor.
Training at our Spring Grove office. Most of your fieldwork this year will be around Belvidere and Poplar Grove — that's where the freshest hail is. The closer you live to that corridor, the better the fit. Best fit if you're in: Spring Grove, Richmond, McHenry, Woodstock, Crystal Lake, Harvard, Marengo, Belvidere, or Poplar Grove.
- Who we're looking forCoachable people who want to build a real career in sales. You don't need roofing or construction experience — we'll teach you everything you need to know. What matters most is your work ethic, resilience, and willingness to learn. If you've served in the military, led teams, or worked hard to support your family, you'll find a home here.
- Training & mentorshipComprehensive onboarding at our Spring Grove office. You'll start by shadowing our top reps to learn the ropes, then transition to setting your own appointments. Our veteran salespeople will coach you side-by-side until you're ready to run appointments solo. Weekly team training calls keep your skills sharp.
- Daily rhythmMondays kick off with the team sales meeting. From there, ~6 hrs of knocking and ~2 hrs of shadowing or inspections per day. Nights and weekends have more homeowners home, so most reps work some combination of evenings and weekends (weekends optional). Rain days, you're on the phones working your set list and following up on past inspections.
- Lead sourcesThree streams. (1) Your own door knocks — you set, you close, you keep 10%. (2) Appointments fed to you by other reps — you close, the splits are 5% setter / 5% closer. (3) During ramp: appointments you set get closed by Austin or Marco — you keep the 5% setter side.
- Metrics you'll trackDoors knocked, doors opened, conversations had, inspections set, inspections that showed, deals signed, deals that stuck. Logged daily. The numbers tell us if the playbook is working for you, and they tell you exactly where to improve.
- TrainingClassroom + ride-along at our Spring Grove office. Live training calls Mondays and Wednesdays at 10 AM CST. 35-chapter playbook with scripts, objection handlers, and the daily SOP. By week 13 you should be running the full job — if you're not, we've failed at hiring you, not the other way around.
- RequirementsReliable transportation, comfortable on a ladder, fine working outside in weather, located in (or willing to relocate to) the corridor above.
You sell the roof. We get it paid for and built.
You knock, you inspect, you sign, and you walk the homeowner through filing the claim. From there, our office team takes the hand-off — adjuster negotiation, supplements, install. The harder you work the front half, the faster the back half compounds.
Knock the door, run the script, set the inspection.
Get the homeowner to say yes to a free roof check. Lock in a time you'll come back (or, if they're home, climb the ladder right now).
Inspect the roof. Document everything.
Photos of every hit. Notes. The dashboard walks you through what to capture and how. (During ramp, Austin or Marco does this with you.)
Sit at the kitchen table. Sign the contract.
Walk the homeowner through what you found, what insurance covers, and what we'll do. (During ramp, your closer leads this — you watch and learn.)
Walk the homeowner through filing the claim.
They file with their own carrier — you're at the table to answer questions in real time. The office is one text away if anything curveball comes up.
Negotiate with the insurance company.
Office handles the adjuster, supplement requests, line items, scope adjustments. You don't argue with insurance — that's our job.
Build the work.
Crew installs the roof, final inspection, depreciation check filed. Two payouts per claim — ACV at approval, depreciation at completion.
Get paid. Friday.
Your % of every check that clears that week — direct deposit. During ramp, you also get your weekly base every Friday for hitting door count.
Most roofing sales jobs are at fly-by-night operations.
This isn't one of them.
If you've sold roofing before, you know the difference. If you haven't, you'll figure it out fast. The legitimacy of the company you work for is the difference between burning every relationship you make and building a career.
Licensed since 2017
Illinois Roofing Licenses #104.019489 (residential) and #105.009527 (commercial). Owner-led, fully insured and bonded. We're not a magnetic-sign truck rolling through after a storm.
A real physical showroom
3340 Mall Loop Dr inside Louis Joliet Mall. Homeowners can walk in and see samples. That's a trust signal you can use at every door: "If you want to see materials in person, our showroom's at the mall."
92% insurance approval rate
We don't file claims on hope — we file with documented evidence. That means the deals you set actually close, which means your commissions actually clear.
Premium product mix
Asphalt shingles up through Brava synthetics, standing-seam metal, and copper. Bigger product mix = bigger contract values = bigger commissions on the same hours of work.
A 35-chapter playbook
Scripts, objection handlers, voicemails, show-rate sequences, the actual probability math — all written down. We didn't make you guess. Reps who follow it earn what we said they would.
Owner answers his phone
Matt Brasic personally onboards every rep, runs the Mon/Wed training calls, and is one Telegram away when you have a question. No call center. No middle manager you'll never meet.
This is a real company with real people.
Showroom, sample wall, manufacturer partners. The same things homeowners can see when they want to verify we exist — which makes your job easier.
The Showroom
Louis Joliet Mall, Joliet IL. Homeowners can walk in and verify we're real — that closes deals at the door.
The Sample Wall
Owens Corning, IKO, Malarkey, Brava, DaVinci. We're certified with all of them. Premium products = premium commissions.
The Team
Our crew with manufacturer reps at the showroom opening. You'll meet most of them in your first month.
Who this works for — and who it doesn't.
We'd rather lose you on this section than three weeks in. Read both columns carefully.
This works if you
- Have sales or leadership experience and want to put it to work in a high-ticket vertical.
- Are money-motivated. Your effort directly determines your income.
- Are coachable. The playbook works — reps who follow it out-earn reps who freestyle.
- Can handle "no." Most knocks end with no answer or a polite decline. The math works because volume is on your side, not because every door goes well.
- Track your own numbers honestly. Doors, opens, conversations, inspections, closes — logged every day.
- Live in or near our Spring Grove–Belvidere corridor (or willing to relocate).
This doesn't work if you
- Want an hourly wage or salary. This is commission-only — you eat what you kill.
- Need a comfortable, predictable work environment. You're outside knocking doors in all weather. It's physically and mentally demanding.
- Aren't willing to follow a playbook. We'll teach you what works, but you have to use it.
- Want to learn passively. The only way to get good is reps — hundreds of doors, dozens of sits.
- Fold after a few rough days. Sales is a mental game. Bad days happen. Tough reps keep knocking.
The stuff you're already wondering.
How does the ramp-up process work?
For your first 2-3 weeks, you'll focus on setting appointments while shadowing our senior reps on inspections and closing presentations. Around week 3-4, you'll start running your own inspections. By week 8, you should be running the full sales process solo — setting appointments, inspecting roofs, presenting to homeowners, and closing deals. Our veteran reps will be with you every step of the way to make sure you're learning and improving.
What does training look like?
Comprehensive onboarding at our Spring Grove office, including classroom sessions and field ride-alongs with senior reps. Weekly team training calls keep your skills sharp. We provide a 35-chapter playbook with scripts, objection handling, and daily SOPs. The key is consistent practice — the more you're in the field using these tools, the faster you'll grow.
Where do leads come from after ramp?
Three streams. (1) Your own door knocks in your assigned zone — you set, you close, you keep 10%. (2) Appointments fed to you by other field reps still in ramp — you close, you get 5%, the setter gets 5%. (3) Your own pipeline of follow-ups from earlier knocks. The longer you're tenured, the more your pipeline compounds on top of fresh activity.
Is this W-2 or 1099?
1099 contractor. This is a commission-only role, not hourly or salaried. You'll fill out a W-9 and direct deposit form before your first day. We pay weekly — your commissions hit your account every Friday for deals that cleared that week.
Do I need roofing experience?
No. Sales experience or leadership experience matters. Roofing/construction experience doesn't actually predict who's good at sales. We provide a 35-chapter playbook with scripts, objection handlers, and the daily SOP — what we need is somebody coachable enough to use it.
How quickly do I get paid?
We pay commissions weekly, every Friday, for any deals that cleared that week. Your first check typically comes about 3 weeks after your first deal is signed. After that, it's weekly. Insurance pays in two chunks — initial ACV check at claim approval, then a final depreciation check when the work is completed. You get your % of each check the Friday after it hits our account.
What hours do I work?
You set them, within the legal knocking window (8 AM–9 PM local to the homeowner). Mondays kick off with our team sales meeting. From there, plan on ~6 hrs of knocking and ~2 hrs of shadowing or inspection follow-up per day. Nights and weekends tend to be highest-yield because that's when homeowners are home — most reps work some combination of evenings and weekends (weekends optional). On rain days, the team works the phones instead — set lists, callbacks, follow-ups.
What equipment do I need?
Reliable transportation, weather-appropriate clothing, and comfort climbing a ladder. Phone, computer, and CRM access we provide. Scripts, lead lists, dashboard tools — all built and ready.
What happens after I submit the form?
You'll get a text within a few hours with a calendar link to book a 15-minute phone screen. We'll explain the role in detail, answer everything, and give you a clear yes/no/next-step. If both sides are a fit, the next step is a 60-minute in-person interview at Spring Grove. Most candidates go from application to first day in the field within 7–10 days.
Tell us a little about you.
Takes about 3 minutes. We'll text you within a few hours with a calendar link for a 15-min phone screen.