Account Manager
Insight Service Solutions & Integrity Painting | Winnipeg, MB $65,000 Base + 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:

Farming our existing customer list to generate new work — we bring you the customer list, you work it, and build a pipeline of current service opportunities.

Prospecting and closing self-generated commercial painting opportunities — you identify, build relationships, and close the work.

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 just a desk job. You'll also 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 part of your responsibility was to develop a pipeline.

You can follow a structured sales process and use a CRM (Pipedrive and Aspire) consistently and accurately.

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 are coachable — you welcome feedback, are eager to be trained, and take pride in getting better every week.

You are 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

Base Salary — so you have cash flow while your pipeline builds.

Commission 10% on GP — for both project and maintenance work.

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–$80,000+ 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

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.

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📌 Account Manager (Manitoba)
🏢 Insightservicesolutions
📍 Manitoba