Mapping Chicago's early-stage Future of Work venture landscape

Over 100 early-stage ventures in Chicago are building the future of work — from AI-powered hiring tools and collaboration platforms to gig-economy marketplaces and vertical SaaS. TechNexus maps the companies reshaping how we hire, manage, and empower the modern workforce.

Through our Reinventing Industries series, TechNexus Venture Collaborative is highlighting key ventures innovating across various industries. This time, we turn our focus to the Future of Work - AI-powered hiring tools, collaboration platforms, gig-economy marketplaces, and vertical software all fall under this category. Over 100 early-stage ventures in Chicago have collectively raised more than $130 million in this space, leveraging technology to redefine how we work, collaborate, manage talent, and more. The evolution of work Covid-19 transformed the way organizations function and people work, driving a shift toward remote and hybrid models. This transformation created both challenges and opportunities, including finding new ways to engage employees, scalable solutions for screening an expanding pool of remote candidates, and sector-specific business operations software to modernize legacy industries. Worker engagement and overall employee wellbeing statistics are at ten-year lows, highlighting a need for better tools to hire and retain talent within organizations. Startups are meeting these demands by developing tailored solutions. Vertical software is modernizing historically non-digital industries, while platforms for hiring and upskilling help companies attract, retain, and upskill talent in a competitive labor market. Chicago’s role as a global business hub fuels this innovation. Home to major employers like Boeing, McDonald’s, and United Airlines, the city’s diverse economy and robust talent pool provide fertile ground for ventures innovating in this space. Anchored by institutions like 1871, mHUB, Workbox, and TechNexus, Chicago also benefits from a strong network of accelerators and coworking spaces. Chicago’s Future of Work startups are redefining the way we work. Areas of innovation Hiring & Offboarding : The average cost per new hire is $4,700 . External recruiters, job postings, background checks, and more all contribute to this expense. In a 2024

By Joey Alfieri at TechNexus Venture Collaborative