Door-to-Door Sales Team Lead

ABOUT SKYLINE EXTERIORS

Skyline Exteriors is a premium outdoor living Design + Build company serving Chicago's most affluent homeowners across the North Shore and western suburbs — Lincoln Park, Winnetka, Hinsdale, Lake Forest, Barrington, and beyond. We build custom patios, hardscapes, pergolas, outdoor kitchens, and complete backyard transformations for homeowners with the vision and the means to invest in their property.

We are not a landscaping company. We are a design and build firm that specializes in turning outdoor spaces into premium living environments. Our average project starts at $10,000. Our larger Design Track projects regularly reach $40,000 to $100,000 and above. The homes we work in have values ranging from $900,000 to $4M+. The neighborhoods we serve have household incomes well above $350,000.

The market is proven. The product sells itself at the door when the right person is delivering the message. We are looking for that person right now.

THE ROLE

This is a field-based, door-to-door lead generation role. You will be working active job site neighborhoods in some of Chicago's best suburbs — knocking doors on streets where Skyline is already building, where the social proof is visible from the road, and where the homeowner is standing behind the door.

Your job is to start genuine conversations with qualified homeowners, identify those with an interest in improving their outdoor space, and book them into a complimentary Design Consultation with our lead Design Consultant. You do not close projects. The Design Consultant closes projects. You open doors — and get paid for every one you open and every project that follows.

What you will do every day:

• Canvass target neighborhoods around active Skyline job sites — 80 to 120 doors per day
• Identify qualified homeowners and start warm, genuine conversations about their outdoor space
• Book complimentary Design Consultations directly into the Design Consultant's calendar
• Brief the Design Consultant on what each homeowner described before every visit
• Track your own numbers daily — doors knocked, conversations had, consultations booked, close rate
• Build your own territory instinct — learning which neighborhoods, times, and approaches produce the best results
• As you grow: recruit, train, and lead your own D2D team under the Skyline flag

COMPENSATION — 100% COMMISSION, FULLY TRANSPARENT

There is no base salary. There is also no earnings ceiling. Here is exactly how you get paid.

Booking Fee — paid when the homeowner attends the consultation:

• $75 per booked Design Consultation, every project size, every time
• Accelerator bonus: once you hit 5 bookings in a single week, every additional booking that week earns an extra $25 on top of the base rate

Project Commission — 3% of closed project revenue — paid when a deposit is collected:

Project SizeYour Commission Per Close$5,000 – $9,999$150 – $300$10,000 – $14,999$300 – $450$15,000 – $24,999$450 – $750$25,000 – $39,999$750 – $1,200$40,000 – $59,999$1,200 – $1,800$60,000 – $99,999$1,800 – $3,000$100,000 – $149,999$3,000 – $4,500$150,000+$4,500+

Our average project is $12,500. Our larger scope Design Track projects regularly reach $40,000 to $100,000 and above. One large project close from a consultation you booked pays more than a full week of booking fees. A single $75,000 outdoor living transformation puts $2,250 in your pocket from one conversation at someone's front door.

Team Override — once you build your own D2D team:

• 1% override on all project revenue closed from consultations booked by any rep on your team
• A team of 3 reps each generating 2 project closes per week at a $15,000 average = $900 per week in override income on top of your personal production

Realistic annual earnings by performance level:

LevelBookings Per WeekEstimated Annual IncomeGetting Started2–3 per week$20,000 – $30,000Solid Performer4–5 per week$40,000 – $55,000Strong Performer6–8 per week$60,000 – $80,000Top 10% Producer10+ per week$100,000+Team Lead (3+ reps)Personal + team production$120,000 – $180,000+

THE CAREER PATH

This is not a rep position indefinitely. This is the foundation of Skyline's sales infrastructure — and the person who builds it gets rewarded for building it.

Stage 1 — D2D Sales Rep | $40,000 – $80,000/yr Start here. Shadow our Design Consultant on 5 live In-Person Consultations before you knock a single door. Begin building your territory. Book your first consultations. The income starts immediately.

Stage 2 — D2D Sales Team Lead | $80,000 – $120,000/yr Hit 5+ bookings per week consistently for 4 consecutive weeks. You begin recruiting and training your first rep. Team override income activates. You are now building a business inside a business.

Stage 3 — Sales Manager | $100,000 – $150,000/yr You are managing a team of 3 to 5 D2D reps. Responsible for their production, training, and results. A base salary is introduced at this stage alongside continued team override income.

Stage 4 — Director of Sales | $130,000 – $200,000/yr You own the entire demand generation function at Skyline. D2D team, referral pipeline, and coordination with the Design Consultant on consultation volume. The equity conversation begins here.

Stage 5 — Partner / Equity Stake | $200,000+ Skyline is being built toward a $100M valuation through a geographic roll-up model across the Midwest. The person who builds the sales infrastructure that makes that possible will have an ownership stake in what gets built. This is not a motivational tagline. It is the business plan.

WHO WE ARE LOOKING FOR

We are not looking for a professional salesperson with a polished resume. We are looking for someone who is hungry, genuinely likeable, coachable, and competitive. The best D2D performers in home services are people who care about winning, can hold a real conversation with anyone, and do not stop when it gets hard.

You are probably the right fit if you:

• Have a track record in a commission or performance-based environment and outperformed your peers
• Can knock 80 to 120 doors in a day and bring the same energy to door 100 as you had to door 1
• Are genuinely personable — people open the door and within 30 seconds feel like they are talking to a neighbor, not a salesperson
• Are coachable — you can follow a process, take feedback, and adapt without ego
• Have your own reliable transportation and a valid driver's license
• Are hungry for income that directly reflects your effort, not your time
• Have natural leadership instincts — you want to teach what you learn and build a team around you
• Are comfortable in affluent neighborhoods and carry yourself with professionalism and confidence

Prior experience that translates directly:

• Any D2D or field sales experience — solar, pest control, roofing, home security, HVAC, telecom
• Restaurant, hospitality, or retail sales — the relationship-building instinct transfers completely
• Athletic or competitive background — the mental toughness required is identical
• Military or trades background — the discipline, routine, and physical resilience are all assets
• Real estate or mortgage sales — the premium homeowner ICP is the same person

No prior experience in outdoor living or landscaping is required. You are not selling a technical product. You are starting a conversation about someone's home and their vision for it.

WHY SKYLINE — WHAT MAKES THIS DIFFERENT FROM EVERY OTHER D2D JOB

Most D2D roles have you selling a subscription, a commodity product, or something the homeowner barely remembers a week later. This is different.

• You are opening the door to a custom, one-of-a-kind outdoor transformation — something the homeowner will look at every day for the next 20 years. The product is genuinely worth being excited about.
• You book the consultation. Our world-class Design Consultant closes the sale. Your commission does not end at the appointment — it ends when the project is complete.
• You are the first D2D hire at Skyline. The team you build is your team. The infrastructure you create becomes the foundation of your next promotion.
• You are working premium Chicago suburbs where the homes are real and the homeowners have the budget to do exactly what they are describing.
• Outdoor living D2D is a greenfield opportunity in this market. No competitor is doing what Skyline is doing in these neighborhoods right now.
• You are trained by a Design Consultant with 40+ years of industry experience before you knock a single door. You will know exactly what you are booking people into because you will have seen it firsthand.

WHAT SKYLINE PROVIDES

• Full onboarding — you shadow our lead Design Consultant on 5 live In-Person Consultations before you start knocking. You see the product, hear the client conversations, and understand exactly what you are booking people into.
• A proven door framework built specifically for our market, our neighborhoods, and our ICP — not a generic D2D playbook.
• Territory support — you are working active job site neighborhoods where Skyline is already building. You are not cold-canvassing blind. The social proof is visible from the road.
• Direct access to Executive Leadership and our Design Consultant for coaching, performance review, and career development.
• Daily Training and process optimization to ensure you are on the right path to success.
• Weekly performance reviews with honest, specific feedback — not a quarterly check-in that tells you nothing actionable.
• A company on a deliberate path to $10M this year and $100M by 2029. The people building the sales infrastructure of a company on that trajectory are the people who grow with it.

HOW TO APPLY

Submit your resume and include a brief note — 3 to 5 sentences — answering this one question:

Tell us about a time you did something hard that most people quit. What was it, how did you approach it, and what happened?

That answer tells us more about who you are than any resume does. We review every application personally. If you are the right fit, you will hear from us within 48 hours.

Job Details:

• Job Type: Full-Time / Independent Contractor
• Pay: 100% Commission — Uncapped
• Location: Chicago, IL — Field-Based (North Shore + Western Suburbs)
• Schedule: Flexible — afternoons and evenings produce the highest conversion rates
• Start Date: Immediately

Pay: $70,000.00 - $180,000.00 per year

Benefits:

• Relocation assistance

Work Location: In person