SERVICE | INTENTIONAL | GROWTH | HUMILITY | TENACITY
Benefits:
- Bonus based on performance
- Competitive salary
- Dental insurance
- Health insurance
- Opportunity for advancement
- Training & development
Title: Estimator & Service Development Manager
Location: Winnipeg, MB | Full-time, Year-Round
Salary: $60,000 – $80,000 + Performance Bonuses
About Us:
Insight Service Solutions Inc. is a growing leader in commercial and residential exterior maintenance in Winnipeg. COR-certified and safety-driven, we provide professional window cleaning, pressure washing, gutter cleaning, dryer vent cleaning, high dusting, caulking, and more. We value dedication, precision, and a high-performance culture. Click here for a video about us!
Why You’ll Love This Role:
- Lead a small remote team of estimators
- Take ownership of projects from estimate to execution
- Influence company profitability and growth
- Monthly team events and annual retreats
- Opportunities to learn, grow, and expand your skills
- Work with a great team of people, click here to see what Paulette has to say about this team!
Key Responsibilities:
- Prepare and manage customer estimate requests
- Follow up on outstanding estimates to close deals
- Complete RFPs with accurate pricing and documentation
- Perform complex time/material calculations for unique projects
- Estimate larger projects and re-price recurring services annually
- Track customer potential vs. awarded value and farm opportunities
- Lead a small remote estimating team
- Maintain excellent client relationships
- Implement efficient, consistent processes
Skills & Requirements:
- 2+ year relevant experience
- Excellent attention to detail and process-driven
- Strong communication and customer service skills
- Proactive, action-oriented, multitasker
- Operationally minded with project management ability
- Comfortable with Google Suite (Gmail, Calendar, Sheets, Docs)
- Experience leading small or remote teams
- Hands-on willingness to learn trade and services
- Full Class 5 MB Driver’s License
- Long-term commitment expected
Preferred Experience:
- Construction, exterior maintenance, or property services
- Estimating or project coordination
- Client-facing or account management
- Operations or process-focused roles
Benefits: Health coverage, year-round employment, team events
Apply Now: Attach your resume and tell us why you’d excel in this key role!
Compensation: $60,000.00 - $80,000.00 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.
(if you already have a resume on Indeed)
Or apply here.
Company Vehicle
Many of our staff take there work vehicle home and drive straight to the job site.
Health Benefits
We have an in house benefits plan that fully covers medical expenses with no employee contribution.
Work Outside
Enjoy the fresh air and get a Tan! Stay active and Fit!
Company Culture Events
We have a Spring, Summer and Winter event where we always have great giveaways and prizes! We love to thank our staff for the hard work they do!
Referral Bonus
We offer our staff a $200 bonus when we hire someone that they refer to us.
Education and Learning Opportunities
We offer and pay for training to eligible employees. This could include leadership training, efficiency training and rope access training.







