Careers
Join the Win Win Redevelopment Team
At Win Win Redevelopment, we take pride in being a family-owned company built on craftsmanship, teamwork, and integrity. Our employees are the foundation of our success, and we’re always looking for skilled, motivated individuals who want to grow with a company that values hands-on experience and long-term commitment.
We offer:
Competitive pay based on experience
Consistent, year-round work in the Chicagoland area
Opportunities for advancement within our growing team
A positive, safety-focused work environment
Open Positions (Now Hiring)
How to Apply
Send your resume or work history to Artie Checchin at artie.checchin@winwinredevelopment.com with the subject line “[Your Position Title] Application.”
You can also call our office at 847-431-9918 for more information.
-
Position: Carpenter
Location: Chicagoland Area (based in Northwest Suburbs)
Employment Type: Full-TimeAbout the Role: We are seeking an experienced carpenter to join our in-house construction team. The ideal candidate is detail-oriented, dependable, and experienced in commercial and industrial remodeling projects. You’ll work alongside our demolition and build-out crews on a wide range of tenant improvements, framing, and finish carpentry.
Responsibilities:
Perform framing, drywall, trim, door, and millwork installation
Read and interpret blueprints and drawing
Maintain a clean, safe, and organized job site
Collaborate with project managers and team members to meet deadlines
Ensure quality workmanship and attention to detail in all phases of construction
Qualifications:
Minimum 2–5 years of carpentry experience (commercial preferred)
Strong understanding of construction safety practices
Reliable transportation to job sites across the Chicagoland area
Ability to work independently and as part of a team
Compensation:
Hourly rate based on experience
Overtime opportunities available
Benefits and advancement potential for long-term employees
-
Position: Laborer / Field Technician
Location: Chicagoland Area (based in Northwest Suburbs)
Employment Type: Full-TimeAbout the Role: We are seeking a reliable laborer / field technician to assist with daily on-site operations for commercial and industrial build-outs. This position plays a vital role in supporting our carpenters, demolition crew, and project managers. The ideal candidate is dependable, safety-minded, and eager to learn the construction trade with opportunities for advancement.
Responsibilities:
Assist with demolition, debris removal, and job site cleanup
Load and unload tools, materials, and equipment
Support carpenters and supervisors with framing, drywall, and finish prep
Operate basic hand and power tools safely
Maintain a clean, organized, and safe work environment
Qualifications:
Previous construction or labor experience preferred (will train motivated candidates)
Must have reliable transportation to job sites throughout Chicagoland
Ability to lift 50+ lbs and work in a fast-paced, team-oriented environment
Strong work ethic and attention to detail
Compensation:
Hourly rate based on experience
Overtime available
Opportunities for skill development and promotion
-
Position: Construction Technician
Location: Chicagoland Area (based in Northwest Suburbs)
Employment Type: Full-TimeAbout the Role: Win Win Redevelopment is looking for an experienced construction technician to join our in-house build-out team. This hands-on position focuses on the installation and repair of commercial and industrial interior systems, assisting in all phases of remodeling projects. You’ll work closely with our carpenters and foremen to help deliver high-quality, on-time results.
Responsibilities:
Perform installation of doors, drywall, ceilings, and light framing
Assist with mechanical, electrical, or plumbing coordination when needed
Operate job site equipment such as lifts, saws, and hand tools
Read and follow construction drawings and site instructions
Maintain safety and quality standards on all tasks
Qualifications:
2–4 years of construction experience (commercial preferred)
Basic understanding of construction drawings and measurements
Strong communication and teamwork skills
Reliable transportation and punctuality required
Compensation:
Hourly pay commensurate with experience
Overtime opportunities
Benefits and long-term growth potential
-
Position: Foreman / Lead Carpenter
Location: Chicagoland Area (based in Northwest Suburbs)
Employment Type: Full-TimeAbout the Role: We’re seeking an experienced foreman / lead carpenter to oversee day-to-day field operations on commercial and industrial build-out projects. This role requires leadership, hands-on carpentry experience, and a commitment to maintaining project quality, safety, and schedule. The ideal candidate will manage crews, coordinate subcontractors, and serve as the on-site liaison between the field and project management team.
Responsibilities:
Supervise daily activities of carpenters, laborers, and subs
Review blueprints and project scopes to ensure alignment with client goals
Lead framing, finish, and build-out work as needed
Manage materials, deliveries, and job site organization
Maintain a clean, safe, and efficient job site
Communicate progress and issues to the Project Manager
Qualifications:
5+ years of carpentry and site supervision experience
Strong leadership and problem-solving skills
Ability to read and interpret construction documents
OSHA 30 certification preferred
Valid driver’s license and reliable vehicle
Compensation:
Competitive hourly or salary based on experience
Vehicle allowance or company truck (depending on role)
Benefits, paid time off, and advancement opportunities