Painting Estimator / Sales Representative

Integrity Painting; Winnipeg; On-site; CAD 45,000 - 90,000; Full time

Job summary

Integrity Painting in Winnipeg, MB seeks an experienced painting estimator who can price jobs accurately, close deals, and independently grow their pipeline. We provide leads and support, with you driving growth and earnings through performance.

The role is not entry-level; you will be expected to hit the ground running, leveraging company leads and self-generated opportunities to maximize income within a full-time framework.

Qualifications

• Minimum 1 year of painting estimating experience (residential/commercial).
• Proven ability to close, follow up, and manage your own pipeline.
• Experience using an estimating tool or standardized system.
• Self-starter mentality when company leads slow.
• Detail-oriented with accurate scope, CRM discipline, and clean proposals.

Responsibilities

• Walk a job, price it right, and close the deal.
• Provide a steady flow of leads from company sources; build your own pipeline.
• Earn more by self-generating leads and expanding your pipeline.
• Maintain CRM discipline and deliver clean, accurate proposals.

Skills

Painting estimating

Sales pipeline management

Estimating software

Self-starter

Detail-oriented

CRM discipline

Driver's license

Professional appearance

Tools

Estimating software

Calculator methods

Job description

Painting Estimator — Integrity Painting | Winnipeg, MB

$45,000–$90,000+ (Recoverable Draw + Commission) | Seasonal with Full-Time Potential

If you're a strong estimator, you already know your value. The question is whether the company you're working with is set up to actually let you earn it. We provide the leads, the admin support, the systems, and the brand. You bring the expertise and the drive. What you earn from there is up to you.

About Us

Integrity Painting is a quality-focused residential and commercial painting company in Winnipeg, operating under Insight Service Solutions — we serve hundreds of clients across the city. We’re growing, and we take our craft seriously.

The Role

We’re looking for an experienced painting estimator who knows how to walk a job, price it right, and close the deal. This is not an entry-level position — we need someone who has done this before and can hit the ground running.

We’ll provide a steady flow of company-generated leads to start. When volume slows, the expectation is simple: you go find the work. The estimators who turn this into a full-time role are the ones who don’t wait to be handed opportunity — they build their own pipeline and earn at a higher rate for doing it.

Commission Structure

• 7% of net sale — company-generated leads
• 10% of net sale — self-generated leads

A recoverable draw of $3,750/month is available while your pipeline builds. Paid weekly once the deposit is collected and the contract is signed. Your earning rate goes up the more you self-generate — the income ceiling here is yours to set.

What We’re Looking For

• Minimum 1 year of painting estimating experience — residential, commercial, or both
• Proven ability to close, follow up, and manage your own pipeline
• Experience using an estimating tool or standardized system (software, calculator method, or equivalent)
• Self-starter mentality — when company leads slow down, you don’t
• Detail-oriented: accurate scope documentation, CRM discipline, and clean proposals
• Valid driver’s license and reliable, presentable vehicle
• Professional presentation — company-branded attire provided

Who We Are

We run on five values: Service, Intentional, Growth, Humble, and Tenacity. We have clear systems, real support, and a team that takes pride in doing things right. If that’s the environment you want to work in, we want to hear from you.

Compensation: $45,000.00 - $90,000.00 per year

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.

Integrity Painting

Serving Winnipeg for Over 35 Years

Integrity Painting was built on a simple idea — do the job right and stand behind your work.

For over 35 years, we’ve helped homeowners and businesses across Winnipeg with reliable, high-quality painting and a process you can trust from start to finish.

Today, that same commitment continues with a renewed focus on communication, consistency, and delivering results the right way.