If you’re looking at roofing sales jobs in Chicago, you’re probably seeing everything from “$100K–$250K” headlines to base-plus-commission roles that look more like traditional outside sales. The truth is: roofing sales can pay extremely well in the Chicago market, but only if you understand how pay plans work, what the job actually involves, and what separates top reps from the rest.
This 2026 guide breaks it down—plain English, no fluff.
Why Chicago roofing sales is its own animal
Chicago-area roofing is shaped by three big realities:
- Storm + insurance work is a major lane (hail/wind events drive spikes in demand).
- Code expectations and scope disputes are common (meaning documentation and follow-through matter).
- Competition is intense (buyers are skeptical; professionalism wins).
That combination creates big opportunity… and big washout risk for reps who thought it was “just knocking doors.”
How much do roofing sales reps make in Chicago in 2026?
There’s no single number, because “roofing sales” includes different roles (lead-gen canvasser, closer, restoration consultant, commercial rep, etc.). But to anchor expectations:
- ZipRecruiter’s reported average annual pay for Roofing Sales in Chicago is about $81,702 as of Jan 12, 2026. ZipRecruiter
- Glassdoor shows a much higher Chicago estimate, but it appears based on very limited reported salaries for that specific title/location, so treat it as a “possible” range—not a guarantee. Glassdoor
- Job boards commonly advertise $100K–$250K “income potential” for commission roles in/around Chicago. Those figures usually assume strong lead flow + strong closing + consistent production. ZipRecruiter+1
A realistic way to think about income
Your pay is usually driven by:
- Lead source (company-provided vs self-generated)
- Sales cycle (retail vs insurance restoration vs commercial)
- Your responsibilities (just selling vs selling + measuring + paperwork + supplements + project handoff)
- Commission structure (percent of contract vs profit split vs tiered plans)
Common commission structures in Chicago roofing sales
1) Percentage of total contract (gross)
This is the simplest to understand: you earn a straight percentage of the job total.
- Many companies and industry discussions commonly reference ~5% to 12% of gross depending on role/support and whether leads are provided. The Roof Strategist+1
- You’ll also see conversations citing roughly 8%–15% in certain markets, but always verify what that percent is based on (gross vs profit vs “net after adjustments”). Facebook
Watch-outs: change orders, supplements, and recoverable depreciation can complicate “what counts” toward commission unless it’s spelled out.
2) Profit split (the “10/50/50” style plan)
One widely discussed model is the 10/50/50 split:
- 10% set aside for overhead
- costs removed
- remaining profit split 50/50 between company and rep Contractors Cloud+1
Some sources describe profit-sharing ranges like 30%–50% of profit (varies by support and responsibilities). The Roof Strategist
Watch-outs: profit splits can look amazing on paper, but payouts can be delayed until the job is collected, and “profit” depends on how the company tracks labor, subs, and overhead.
3) Hybrid: base + commission (often for more “sales professional” roles)
These roles may offer:
- a smaller base
- lower commission %
- company-provided leads
- vehicle/phone/benefits (varies)
Good fit if: you want stability, training, and a longer runway.
What you’ll actually do in a Chicago roofing sales job
Most Chicago-area roofing sales roles include some mix of:
Prospecting & lead generation
- Door-to-door canvassing (especially after storms)
- Networking with realtors/property managers
- Referrals and neighborhood saturation
Inspections & documentation
- Ladder/roof access (comfort with heights is non-negotiable)
- Photos, measurements, notes
- Explaining findings to homeowners clearly
Insurance process guidance (common in restoration sales)
- Helping the homeowner understand next steps
- Meeting adjusters on-site
- Documenting scope issues (without overpromising outcomes)
Some companies explicitly frame the role as guiding the customer through the insurance process and paperwork. Romexterra Restoration
Closing & contract
- Presenting options
- Handling objections
- Managing expectations on timeline and pricing
Job handoff + communication
- Keeping the homeowner calm and informed
- Coordinating with production so the experience stays smooth
What to ask before you accept a roofing sales job (important)
Bring these questions to every interview:
- Is this W2 or 1099? (Tax and benefits implications are huge.)
- Are leads provided? If yes, what percent of my deals should I expect to be company-generated?
- What exactly is commission based on?
- gross contract? profit? collected funds?
- When do commissions pay out? (At contract, at start, at completion, or after final payment?)
- Do supplements/change orders count toward commission?
- What support is provided? (truck, ladder, phone, training, CRM, marketing)
- What are the minimum activity expectations? (doors/day, inspections/week, closes/month)
- Who handles production problems? (If you “own it,” you’re also part project manager.)
If they can’t answer clearly—or the answers keep changing—treat that as a warning.
What top roofing sales reps in Chicago do differently
The best reps consistently:
- Run a clean inspection + photo process
- Explain scope and timelines without hype
- Follow up relentlessly (but professionally)
- Track every lead in a CRM
- Stay organized through insurance friction
- Build referral flywheels (neighbors, family, realtors)
This is where “storm chasing” energy dies and real careers begin.
Roofing sales jobs in Chicago: who this is best for
You’ll do well if you:
- like performance pay and competition
- can handle rejection without spiraling
- are comfortable on roofs and around construction
- can communicate calmly with homeowners under stress
You’ll struggle if you:
- need guaranteed pay
- hate follow-up
- avoid conflict/confrontation
- don’t want to learn the basics of the insurance restoration process
Hiring in Chicagoland?
If you’re exploring a roofing sales role and want a quick reality check on a pay plan—or you’re looking to join a team that does storm restoration the right way—reach out.
Allied Emergency Services, Inc.
Phone: 800-792-0212
Email: info@alliedemergencyservices.com
Apply: https://www.careers.alliedemergencyservices.com/job/chicago-area-roofing-sales-rep-high-commission
If you’d rather talk to a real person immediately, call the number above and ask for a recruiting or sales manager.
FAQ: Roofing sales in Chicago (2026)
Do roofing sales jobs in Chicago require experience?
Not always. Many companies hire entry-level reps and train them, but your success depends on coachability and activity. Job boards show plenty of “will train” postings. ZipRecruiter+1
What’s a normal roofing commission?
You’ll commonly see 5%–12% of gross on percentage plans, or profit-sharing models that can land around 30%–50% of profit depending on structure and role. The Roof Strategist+1
Can I really make $200K+ in roofing sales?
It’s possible, and it’s frequently advertised as “income potential,” but it usually requires consistent production, strong closing, and either strong lead flow or strong self-generation. ZipRecruiter+1
Is roofing sales mostly door-to-door?
In storm restoration, often yes—especially right after hail/wind events. Retail and commercial sales can be less D2D and more relationship-driven.
