Outside Sales Representative - Door-to-Door (Window Cleaning Services) Barrie & Simcoe County | Paid Training + Uncapped Commission + Team Overrides
We're hiring 3 outside sales representatives - and likely more - to build out a real sales team for our window cleaning business across Barrie, Orillia, and Simcoe County. This isn't a "casual gig." It's a structured, high-intensity D2D sales operation modelled after the top sales organizations in North America. Read everything below before applying.
What This Job Actually Is
You'll spend your day walking residential streets, knocking on doors, pitching homeowners on our window cleaning service, and closing them on the spot. You'll do this 5-6 days a week, in heat, in cold, in rain.
You will get rejected. A lot. Most people who try D2D quit in the first 7 days. Some quit on day 1. We are telling you that up front because we'd rather you decide now than waste your own time.
Why You'd Still Want to Do It
Door-to-door sales is one of the most valuable skills you can build. It teaches you to handle rejection, read people, close decisions, communicate with strangers, and operate without supervision. Salespeople who survive D2D become sales directors, business owners, and entrepreneurs. The ones who quit go back to retail.
If you give this 30 days, you'll have an experience and a skill set that shapes the rest of your career. Whether you stay with us or move on, you'll carry it forever. You may as well get paid well to learn it.
What You'll Earn
- Paid training: $18/hr for your first 5 days while you learn the system, study materials, and ride with a top closer
- Commission after training: 30% of every first-time customer you close
- Volume bonus: 35% commission after 15+ closes in a calendar month
- Upsell bonus: 30% on add-ons (eavestroughs, pressure washing, screens)
- Retention milestones: $200 at 14 days, $500 at 30 days, $500 at 60 days, $1,000 at 90 days
- Loyalty bonus: $50/month every month you stay past 30 days
- Daily and weekly contests: cash prizes for most doors knocked, most doors opened, first close, biggest ticket, biggest cuss-out story, and more
- Recruiting overrides: after 90 days you can recruit your own team and earn 5% override on every rep you bring on (for 6 months), then 2% forever
Average job: $250–$400. Realistic weekly earnings for committed reps: $1500–$2000. Top closers in this industry earn $10,000–$15,000+/month. We're being honest: most people will never get there. The few who do build careers out of it.
What Your Day Looks Like
- 9:00–10:30 AM: Team meeting - leaderboard review, role-play, pitch drills, objection practice on freestanding doors
- 10:30 AM–7:00 PM: On the doors (with breaks for food and reset)
- 7:00 PM: Optional debrief, war stories, prep for tomorrow
We meet 3-4 times a week. Role-play every day. Training is mandatory for month 1.
Pre-Start Requirements (Before You Set Foot on a Door)
Before your first paid day, you'll be asked to:
- Read the closer handbook we'll send you (or listen to the audiobook)
- Complete a short quiz (10 questions, open-book) - you'll need to pass to start training
This isn't busywork. The reps who don't engage with the material quit in week 1 every single time. We've stopped trying to fight that pattern and started filtering for it instead.
Who Tends to Make It
- Former athletes who know how to grind through losing seasons
- Servers, bartenders, and hospitality workers used to fast decisions and thick skin
- People who've done D2D, MLM, or commission sales before and didn't hate the work
- 20-30 year olds who want to learn a skill, not just earn a paycheque
- Career-changers who realized office or trades work wasn't for them
- Anyone who's had to do something hard every day and didn't quit
Who Doesn't
- People looking for easy money
- People who can't separate "no" from rejection of themselves as a person
- People who skip morning training because they "already know it"
- People whose partner or family doesn't support the role (week 1 is brutal and you need backup at home)
- People who think they'll learn the trade and start their own company in 60 days
What You Need
- Reliable transportation
- Smartphone
- Willingness to wear branded gear and follow the system
- Mental toughness - the only person who knows how the last door went is you
Schedule, Contract, Logistics
- Full-time, 7-month seasonal contract with strong potential to extend year-round for producers
- Daily team-based training, individual canvassing territory
- In-person work across Barrie, Orillia, Innisfil, and surrounding Simcoe County
- 3 positions open immediately - additional spots as we scale
Apply through Indeed. First interviews this week, training starts within 14 days. If you read this ad and felt "that sounds like me, even the hard parts" - we want to talk.
Pay: $18.00-$60.00 per hour
Application question(s):
- Reliable transportation to canvassing zones in Simcoe County?
- Comfortable working in a 100% commission-based role after paid training week?
- Can you commit to attending 1-2 hour morning training every workday for month 1?
- Can you start within the next 2 weeks?
- Any door-to-door, commission sales, MLM, or canvassing experience?
- Tell me about a time you had to do something every day that you didn't want to do - what kept you going?
- A homeowner says "not interested" and starts to close the door. What's your next move?
Work Location: In person
