Junior Flat Roof Estimator

Oakwood Roofing & Sheet Metal Co. Ltd. | Winnipeg, MB (on site)

Pay and benefits

- $50,000 to $57,000 per year, based on experience
- Full-time
- Health, dental, and vision insurance
- Paid time off and holidays
- Paid, hands-on training with a senior estimator
- Safety gear and tools provided
- A transparent path to Estimator and Senior Estimator roles

About the role

Want to start a career in construction estimating? We want a motivated person to learn flat roof estimating from the ground up and grow with us. You don’t need estimating experience. We’ll train the right person. Attitude and willingness to learn matter more than a perfect resume.

What you’ll do

On site:

- Visit job sites to measure roofs and record existing conditions: drainage, penetrations, flashing, and deck condition
- Take photos and notes, and keep them organized for each project

In the office:

- Take accurate measurements by hand and with digital tools, including Estimating Edge takeoff and estimating software
- Calculate material quantities, labour hours, and equipment needs
- Prepare estimates and proposals with guidance from a senior estimator
- Get supplier pricing and keep our material cost sheets up to date
- Learn our pricing methods, warranty requirements, and manufacturer specs

With customers and the team:

- Answer customer questions and follow up on open quotes




- Hand off awarded jobs to project managers and crews

What you need

- College education
- Solid basic math, including measurements, areas, and unit conversions
- Comfort with Excel or Google Sheets, and with computers in general
- Strong attention to detail
- Clear written and spoken communication
- Valid driver’s licence and reliable transportation
- Able to climb ladders, walk on roofs, and work outdoors in all kinds of weather
- Able to lift up to 50 lbs (about 23 kg)
- Able to work on site in Winnipeg (this is not a remote role)

Nice to have (not required)

- 1 to 2 years in roofing, construction, or a related trade
- Experience reading blueprints or building plans
- Familiarity with estimating or construction software (e.g., The EDGE, Autodesk, Procore)
- Knowledge of commercial flat roof systems
- Fall protection or other roof safety training

Our hiring process

1. Apply with your resume by December 6, 2026.
2. We review every resume.
3. We contact the people we want to meet to set up an interview.

Your privacy

We use your resume and contact details only to review your application for this job. We keep them private. We share them only with the people involved in hiring.

About Oakwood

Oakwood Roofing & Sheet Metal Co. Ltd. is a commercial and residential roofing and metal cladding contractor based in Winnipeg, serving Manitoba, and Ontario.

📌 Junior Flat Roof Estimator (Winnipeg)
🏢 Oakwood Roofing u0026 Sheet Metal Co
📍 Winnipeg