Job Description

Benefits:

• Bonus based on performance
• Competitive salary
• Dental insurance
• Flexible schedule
• Health insurance

Sales Representative — Building Services

Insight Service Solutions & Integrity Painting | Winnipeg, MB $45,000–$75,000+ (Base Draw + Commission) Full-Time | Monday–Friday
About Us
Insight Service Solutions is a leader in commercial exterior building maintenance and cleaning services in Winnipeg — including window cleaning, gutter cleaning, and dryer vent cleaning. Integrity Painting is our residential and commercial painting division. Together, we operate as one team with over 40 employees and 15+ service vehicles, serving hundreds of commercial and residential clients across the city.

We're growing, and we're looking for the right person to help us grow faster.

The Role
This is a revenue-generating sales position that spans both companies. You'll be responsible for three things:

1. Attending and closing company-provided residential painting estimates — we bring you the leads, you show up, quote the work, and close the deal.
2. Prospecting and closing self-generated commercial painting opportunities — you go find the work, build the relationship, and bring it home.
3. Hunting new commercial maintenance contracts for Insight Service Solutions — you identify buildings and property managers who need our services and develop them into clients.
   
   

This is not a desk job. You'll be in the field meeting prospects, on the phone building pipeline, and in our CRM keeping your opportunities moving. You'll have real autonomy in how you prospect and build relationships — what matters most to us is that you show up with a strong work ethic and the willingness to push through when things get tough.

What We're Looking For

The right candidate is driven, coachable, and disciplined.

• You have a proven track record in sales — ideally in a role where you sold a defined set of products or services within an established company, not as a freelancer or independent operator.
• You can follow a structured sales process and use a CRM (Pipedrive and Aspire) consistently and accurately. If you've never used a CRM before, that's okay — but you need to be someone who respects systems and is willing to learn them.
• You are comfortable with cold outreach — calling, emailing, dropping in, networking at industry events. Hunting is a core part of this role, not a side task.
• You're coachable — you welcome feedback, you're eager to be trained, and you take pride in getting better every week.
• You're personable and genuine — clients trust you, colleagues enjoy working with you, and you build relationships that last.
• Experience in the painting, property maintenance, restoration, or cleaning industry is a strong asset — but not required. What matters more is your ability to learn quickly and sell within a structured environment.
  
  

What You'll Get

• $3,750/month recoverable draw against commissions — so you have cash flow while your pipeline builds.
• Commission rates from 5%–15% depending on the type of work and how much of the sales process you own.
• Year-2 residual commissions on renewed maintenance contracts you bring in — your book of business pays you back.
• Realistic Year-1 earning potential of $70,000–$75,000+ based on hitting targets across both companies.
• Health & wellness benefits after a 3-month probationary period.
• Mileage reimbursement at $0.50/km for work-related travel.
• Laptop and tablet provided. You bring your own vehicle and cell phone.
• A company that has clear systems, defined processes, and real support — we've built the infrastructure, we just need the right person to plug into it.
  
  

What a Typical Week Looks Like

• Attending 3–5 residential painting estimates provided by the company
• Making prospecting calls and site visits to commercial property managers and building owners
• Logging all activity in Pipedrive and Aspire — same day, every day
• Following up on outstanding proposals and moving pipeline deals forward
• Attending a weekly team meeting with your pipeline report prepared
• Networking at industry events (BOMA, PPMA) as opportunities arise

How to Apply

If you want a role where no two days look the same, relationships matter, and your effort directly drives your income — come build something with us.

Respond to this post with your resume and cover letter to let us know why you think you’d be a great fit for our team! Visit us at insightservicesolutions.ca to learn more about our mission and our crew.
Compensation: $45,000.00 - $75,000.00 per year

What a beautiful SIGHT!

Seeing a Team come together and rally to get a job done is what we love. We know that creating an amazing team and company culture does not happen by chance but instead is intentionally created and developed over time. That is why we are looking for people who are: Humble enough to admit fault and ask questions, Tenacious enough to try and find a way to get the job done and love Teamwork
Field Technicians

If you love teamwork, clean spaces and find yourself wondering “Why doesn’t somebody clean that” We have a job for you! Spend your days working outside getting fresh air and enjoying the satisfaction of seeing instant results. Everyday we uncover the beauty that's already there. From cleaning windows to pressure washing, we are making Winnipeg's Skyline Shine!

Office Team
We are growing and are looking to add amazing people to our team. We have doubled in size over the last 2 years and have no plans on slowing down. Our growth has been fueled by the desire to always improve, challenge ourselves and be amazing at whatever we put our mind to. We love serving our customers and overcoming challenges together. We have fun and we work hard. If you are looking to work somewhere that feels like family and has a passion for growth -we would love to chat with you!

Come work with us :)

Member businesses are independently owned and operated. Your application will go directly to the member business, and all hiring decisions will be made by the management of that business. All inquiries about employment at these businesses should be made directly to the business location, and not to the International Window Cleaning Association.