Careers at Windward Roofing & Construction

Why Work at Windward?

Windward Roofing & Construction is not a faceless corporation. We are a family-owned business where every team member is known by name, contributions are recognized, and careers are built over decades rather than months. Founded in 1984 by Randy Kuhn and now led by the second generation of the Kuhn family, Windward has grown into a multi-state commercial roofing operation with approximately 100 team members serving Illinois, Wisconsin, Michigan, Indiana, and Florida.

We are always looking for motivated, skilled professionals who take pride in their work and want to be part of a company that treats its people right. Whether you are an experienced commercial roofer, a project manager looking for your next challenge, or someone just starting out in the trades, Windward offers a workplace where you can grow.

What We Offer

At Windward, we believe that taking care of our people is the foundation of taking care of our clients. That is why we invest in competitive compensation, comprehensive benefits, and a work environment built on mutual respect and shared purpose.

Competitive pay based on experience and skill level
Health insurance and benefits package
Paid time off and holidays
Year-round work with a stable, established company
Career advancement opportunities — we promote from within
Training and development including manufacturer certifications
Safety-first culture with comprehensive OSHA training
Modern equipment and well-maintained fleet

Positions We Typically Hire For

While specific openings vary based on project demand and seasonal needs, we regularly hire for the following types of positions across our Illinois, Florida, Wisconsin, Michigan, and Indiana operations:

Field & Production

Commercial Roofing Foremen
Journeyman Roofers (TPO, EPDM, Metal, BUR, Modified Bitumen)
Roofing Laborers & Apprentices
Sheet Metal Mechanics
Waterproofing Technicians
Superintendents

Office & Management

Project Managers
Estimators
Account Managers / Sales
Administrative & Office Support

How to Apply

Interested in joining the Windward team? Send your resume and a brief introduction to:

✉ Email Your Resume

You can also reach us by phone at (844) 880-8844 or stop by our office at 919 S Sacramento Blvd, Chicago, IL 60612 during business hours (Mon–Fri, 7:00 AM – 5:00 PM).

We review every application and will be in touch if there is a fit. Windward Roofing & Construction is an equal opportunity employer.

Our Culture

What Makes Windward Different

We are not just another roofing company. Here is what our team members value most about working at Windward.

Family Atmosphere

Ownership knows every employee by name. Decisions are made by people who work alongside you, not by a distant corporate office. When you join Windward, you join a family.

Career Growth

Many of our foremen, superintendents, and managers started in the field. We invest in training, support manufacturer certifications, and promote from within whenever possible.

Safety First

Every crew member goes home safe. Period. Our comprehensive safety program, OSHA training, and zero-tolerance approach to unsafe conditions protect our people every single day.

Competitive Pay & Benefits

We offer competitive wages, health insurance, paid time off, and year-round work with a company that has been in business for over 40 years. Stability you can count on.

Five-State Operation

With projects across Illinois, Wisconsin, Michigan, Indiana, and Florida, Windward offers diverse project experience and opportunities in multiple markets.

Quality Work

We take pride in what we build. Our manufacturer certifications, 10,000+ completed projects, and long-term client relationships are proof that quality work matters here.

Join the Windward Team