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)

construction worker fastening metal profile frame to to wall for drywall bulkhead

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-Time

    About 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-Time

    About 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-Time

    About 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-Time

    About 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