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Added 40 mins ago
AT
Flatbed Company Driver
Armour Transportation Systems
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- Full-time
Career Advancement – We offer opportunities to grow within the company and become an Owner Operator
Added 40 mins ago
SD
Pharmacist, Hourly Part Time Flexible Shifts Greenlight Requisition
Shoppers Drug Mart
Mississauga, ON
- Part-time
Each store has an Associate-Owner, so you will work for a local business owner while having the support of a national brand. Benefit from a purchase discount program, flexible and varied…
Added 55 mins ago
TS
Owner Operator
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- Full-time
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Added 1 hour ago
SD
Merchandiser, Hourly Part Time Day
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- Part-time
Each store has an Associate-Owner, so you will work for a local business owner while having the support of a national brand. Benefit from a purchase discount program, flexible and varied…
Added 1 hour ago
SD
Merchandiser, Hourly Part Time Day Greenlight Requisition
Shoppers Drug Mart
North Vancouver, BC
- Part-time
Each store has an Associate-Owner, so you will work for a local business owner while having the support of a national brand. Benefit from a purchase discount program, flexible and varied…
Added 1 hour ago
LC
Owner/Operator - Pickering, ON
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Added 1 hour ago
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Added 2 hours ago
LC
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- Part-time
Each store has an Associate-Owner, so you will work for a local business owner while having the support of a national brand. Benefit from a purchase discount program, flexible and varied…
Added 2 hours ago
SD
Cashier, Hourly Part Time Day Greenlight Requisition
Shoppers Drug Mart
London, ON
- Part-time
Each store has an Associate-Owner, so you will work for a local business owner while having the support of a national brand. Benefit from a purchase discount program, flexible and varied…
Added 2 hours ago
MC
Maintenance Technician
MatchBox Consulting Group
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- Full-time
MatchBox Consulting Group is partnering with a well-established real estate owner, developer, and property manager to hire a Maintenance Technician for a purpose-built rental community in…
Added 3 hours ago
WI
Outside Sales Representative
Winwire International Inc.
Mississauga, ON
- Contract
Every local business has the same problem. The phone rings while the owner is with a customer, under a sink, or locking up for the night, and that caller goes to whoever answers next.
Added 3 hours ago
MT
Dispatcher
MAJCO TRUCKING
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- Full-time
Assign shipments to company drivers and owner-operators based on equipment availability, location, capacity, and service requirements.
Added 3 hours ago
SD
Beauty Manager, Hourly Full Time Day Greenlight Requisition
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- Full-time
Work in conjunction with the Associate-Owner and Front Store Manager
Added 3 hours ago
SD
Merchandiser, Hourly Part Time Flexible Shifts Greenlight Requisition
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- Part-time
Each store has an Associate-Owner, so you will work for a local business owner while having the support of a national brand. Benefit from a purchase discount program, flexible and varied…
Added 3 hours ago
SD
Pharmacy Assistant, Hourly Full Time Day
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Vancouver, BC
- Full-time
Each store has an Associate-Owner, so you will work for a local business owner while having the support of a national brand. Benefit from a purchase discount program, flexible and varied…
Added 3 hours ago
SD
Pharmacy Assistant, Hourly Part Time Day
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Vancouver, BC
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Each store has an Associate-Owner, so you will work for a local business owner while having the support of a national brand. Benefit from a purchase discount program, flexible and varied…
Added 3 hours ago
SD
Pharmacist, Hourly Part Time Flexible Shifts Greenlight Requisition
Shoppers Drug Mart
Ottawa, ON
- Part-time
Each store has an Associate-Owner, so you will work for a local business owner while having the support of a national brand. Benefit from a purchase discount program, flexible and varied…
Added 4 hours ago
SD
Pharmacist, Hourly Part Time Day
Shoppers Drug Mart
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- Part-time
Each store has an Associate-Owner, so you will work for a local business owner while having the support of a national brand. Benefit from a purchase discount program, flexible and varied…
Added 5 hours ago
SD
Pharmacist, Hourly Part Time Day
Shoppers Drug Mart
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- Part-time
Each store has an Associate-Owner, so you will work for a local business owner while having the support of a national brand. Benefit from a purchase discount program, flexible and varied…
Added 5 hours ago
SD
Merchandiser, Hourly Part Time Evening
Shoppers Drug Mart
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Added 5 hours ago
SD
Pharmacist, Hourly Part Time Day
Shoppers Drug Mart
Toronto, ON
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Each store has an Associate-Owner, so you will work for a local business owner while having the support of a national brand. Benefit from a purchase discount program, flexible and varied…
Added 5 hours ago
C
Client Engagement Associate
CIBC
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- Full-time
Problem solving - Listen, gather information, and put yourself in the client’s shoes. Act like an owner by taking accountability for client issues, and know when to lean on others to create…
Added 6 hours ago
OF
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- Other
A supportive owner-operator and a small, friendly team
Added 6 hours ago
C
Client Engagement Associate
CIBC
Ganges, BC · BC · Salt Spring Island-Ganges
- Full-time
Problem solving - Listen, gather information, and put yourself in the client’s shoes. Act like an owner by taking accountability for client issues, and know when to lean on others to create…
Added 7 hours ago
MA
B2B Sales & Business Development | Commission Only | Miles Ahead Hosting -
Miles Ahead Hosting
Remote, Canada
- $80,000 to $120,000 CAD / year
- Full-time
- Remote
You should be able to explain what we do naturally, make the value understandable and give a business owner a compelling reason to continue the conversation. There may also be opportunities…

Winwire International Inc.

Outside Sales Representative

Mississauga, ON, Canada

Contract

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Applications open in a new tab.

Job details

Job type: Contract
Apply by: Dec 1, 2026
Posting language: English
Posted: Nov 1, 2026

Original job description

Outside Sales Representative - AI Receptionists & Websites for Local Businesses

Mississauga, Brampton & the GTA · Phone + in person · Independent contractor · Commission only

Every local business has the same problem. The phone rings while the owner is with a customer, under a sink, or locking up for the night, and that caller goes to whoever answers next.

We fix that. You'll be the person who finds the businesses that need it, and walks in to show them how.

About Winwire

Winwire International Inc is a Mississauga company that gives small businesses what they can't staff themselves:

An AI receptionist that answers the business's own number day and night. It takes orders, bookings, job requests and messages, and sends the owner a recording and transcript of every call.
A professional website, live in ten business days.
Done-for-you outreach (lead generation) run by real people.
Licensed Ontario recruiting.

The role: dial, qualify, visit, close

Dial out to qualify. Call local businesses from our sales app to find the owners with a real need and set up a time to drop by. You can also walk in cold. Whichever works for you.
Visit and close. Meet the owner or manager at their store, restaurant, clinic, auto shop or trade business, and play them a live AI receptionist call on your phone. They hear it answer, and the idea sells itself far better than a brochure would.
If they're ready, they sign and pay through our secure link, and our team builds and launches everything. If they're interested but not ready, you log them and our callers follow up. You still get paid if they buy later.

Why this is worth your time

A real share of the sale: 30% of net revenue on every sale you close.
You earn from the doors that say "not yet". When our callers close a business you logged, within 90 days of your visit, you earn 10%, and nothing comes out of your 30%.
No cap on earnings.
Your schedule. No set hours, no minimum calls or visits, and no exclusivity, so you can keep your other work.
You sell, and we do the rest. Callers follow up your leads, and our team builds, launches and supports every client. You never chase an invoice or fix a website.
Everything you need is supplied: the calling line, lead lists with a research note on each business, a sales app on your phone, live demos, a price sheet, talking points, answers to common objections, and training with our Sales Head.

How pay works

A sale is a client's first payment. You earn 30% of the net revenue on it: what the client paid, minus tax, refunds and the direct cost of building and delivering what they bought.
Commission can be invoiced 30 days after the client pays (their money-back window). You create the invoice in the app in one tap, and it's paid within 15 business days, in Canadian dollars.
This is commission only, performance based. There is no base pay, and travel, phone and data costs are your own. We tell you now so there are no surprises.

What you'll do

Call businesses in their working hours (the app only lets calls out from 9 a.m. to 7 p.m. their time) and visit during their open hours, in the areas we agree on.
Speak to the decision maker and play a live demo.
Log each visit in the app while you're there. Your phone records the location and a photo of the storefront, which is how you get credit for every lead.
Close the ready ones. They pay through our link, and you never handle cash or card details.

Who you are

You enjoy talking with business owners, on the phone and face to face, and walking in unannounced doesn't bother you.
You take "no" gracefully and leave when you're asked to.
You're honest. You'd never promise something we can't deliver.
Experience in retail, hospitality, door-to-door, phone sales, B2B sales, real estate or insurance helps, or running your own business. If you can play a video on your phone, you can give the demo.

Requirements

Legally able to work in Canada as a self-employed contractor. You handle your own taxes, and we issue a T4A where one is required.
A smartphone with a data plan, and a way to get around the GTA by car or transit.
Fluent English. A second language common among GTA business owners, such as Punjabi, Hindi, Urdu, Tamil, Mandarin, Cantonese, Arabic, Tagalog, Portuguese or French, is a real advantage.

The details

Independent contractor agreement, 12 months, with a review every 6 months. Either side can end it with 14 days' notice.
Standard confidentiality and non-solicitation terms.
We never charge a fee to join.

How to apply

Apply here. In a few lines, tell us which part of the GTA you'd like to cover, when you're usually available, and something you've sold.

Winwire International Inc · Mississauga, Ontario

Apply About employer

More about this job

Responsibilities

Call local businesses to qualify prospects, arrange visits, demonstrate the AI receptionist, and close sales with decision makers. Record visits and leads in the sales app; follow-up callers and the delivery team handle subsequent follow-up and client setup.

Requirements

Applicants must be legally able to work in Canada as a self-employed contractor, have a smartphone with a data plan, and be able to travel around the GTA by car or transit. Fluent English and comfort with phone and in-person outreach are required; relevant sales or business ownership experience and fluency in another language common among GTA business owners are advantages.

Skills

Outside Sales
Cold Calling
In-Person Sales
Lead Qualification
Lead Generation
B2B Sales
Sales Closing
Product Demonstration
Relationship Building
Objection Handling
Communication
Customer Outreach
Sales Lead Logging
Smartphone App Use

Visa sponsorship

Not detected in the job text

Keywords

AI Receptionist
Websites
Local Businesses
Outside Sales
Commission Only
Independent Contractor
B2B Sales
Cold Calling
Lead Generation
Lead Qualification
In-Person Sales
Sales Demonstrations
Sales Closing
Sales App
Lead Lists
Follow-Up
Net Revenue Commission
Small Business
Mississauga
Brampton
Greater Toronto Area
Ontario

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