Leaders from industry and the workforce development system should develop better ways to share information. Each makes significant investments affecting what the region’s labor supply has to offer and where the labor supply can be enhanced. Without adequate communication and collaboration, recurring misalignment can squander mutual benefits to businesses and workers. Broad, ongoing, and meaningful industry engagement provides the workforce system with real-time signals on employers’ needs and training opportunities. In turn, education and training programs can better prepare participants to solve problems adeptly, adopt new technologies, and operate in the evolving contexts that employers face. Such information should serve as a basis for collaboration and guide how limited resources are allocated in response to regional needs. The region’s Workforce Investment Boards (WIBs) and their workforce development partners have set national best practices to address the substantial needs among low- and middle-skilled workers. For example, several regional partners including the Skills for Chicagoland’s Future and the Chicago Cook Workforce Partnership have developed strong demand-driven strategies and programs. Moving forward, they should continue to be key implementers for engaging industries. With the implementation of WIOA, employers have multiple specific ways to participate in workforce investments. These include sharing information with the region’s American Job Centers regarding job postings and leads, working with education and training providers to identify needed skill competencies and qualifications, and retaining job seekers in employment by helping to articulate and implement career pathways. In particular, employers and the workforce development system should collaborate to use candidates’ cross-sector skills and reduce procedural barriers to overlooked talent.