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Outside Sales Representative

Posted on Sept. 4, 2026

  • Full Time

Outside Sales Representative job opportunity

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Location: Winnipeg, Canada

Job Type: Independent Contractor (Commission-Based)

Expected Annual Earnings: $75,000–$150,000+

About Watson Exteriors

Watson Exteriors is one of Winnipeg's growing exterior restoration and roofing companies, dedicated to providing homeowners with high-quality roofing solutions and exceptional customer service. As we continue to expand, we're looking for driven individuals who want more than just a sales job, they want an opportunity to build a long-term career with significant income potential and rapid advancement into leadership.

Position Overview

As a Door-to-Door Roofing Sales Representative, you'll generate new business by canvassing residential neighborhoods, educating homeowners about our roofing services, and scheduling inspections. You'll manage customer relationships throughout the sales process while working independently with the support of an experienced team.

This is an excellent opportunity for highly motivated individuals who enjoy meeting new people, controlling their own income, and being rewarded for their performance.

Compensation

  • Independent Contractor Position
  • Expected annual earnings of $75,000–$150,000+
  • Commission-based compensation
  • Earn 6%–10% commission on each completed project
  • Commission percentage increases based on sales performance.

Responsibilities

  • Prospect for new business through door-to-door canvassing
  • Build relationships with homeowners
  • Educate customers about roofing products and services
  • Schedule roof inspections and consultations
  • Follow up with prospective customers
  • Manage your sales pipeline and customer communications
  • Represent Watson Exteriors with professionalism and integrity
  • Meet and exceed monthly sales goals

Qualifications

  • Must reside in Winnipeg, Canada
  • Reliable personal vehicle
  • Valid driver's license
  • Comfortable working outdoors and walking neighborhoods
  • Strong communication and interpersonal skills
  • Self-motivated with a strong work ethic
  • Ability to work independently
  • 1–2 years of sales experience (door-to-door, retail, customer service, or other sales experience is an asset but not required)
  • Experience in construction, roofing, or home services is beneficial but not necessary

What We're Looking For

We're looking for individuals who are:

  • Competitive and goal-oriented
  • Coachable and eager to learn
  • Comfortable speaking with homeowners
  • Resilient and persistent
  • Professional and dependable
  • Motivated by unlimited earning potential

Growth Opportunities

Watson Exteriors is expanding quickly, and we believe in promoting from within whenever possible. Top-performing representatives will have opportunities to move into leadership and management roles as the company continues to grow.

If you're looking for a career where your effort directly determines your income and advancement opportunities, we'd love to hear from you.

Why Join Watson Exteriors?

  • Unlimited earning potential
  • Performance-based commission increases
  • Flexible schedule
  • Ongoing sales training and mentorship
  • Career advancement opportunities
  • Join a fast-growing company with a supportive team culture

Apply today and start building a rewarding career with Watson Exteriors.

Pay: $70,000.00-$150,000.00 per year

Benefits:

  • Company events

Work Location: Hybrid remote in Winnipeg, MB (Eastern Manitoba Region)


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