chicago-startup
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Alex Kerr
Alex Kerr is the CEO and founder of Trajektory, a Chicago-based sponsorship analytics platform he started in 2020 to fix the broken, incomplete data that sports rights holders and brands relied on to value their partnerships. A former baseball player at Kenyon College and business intelligence leader at Monumental Sports & Entertainment, Kerr built Trajektory's first product in Tableau before turning it into an AI-driven platform that now tracks more than $180 billion in annual sponsorship value and works with roughly half of the major professional teams in North America. In May 2026 the company raised $8 million to expand its engineering, sales, and AI capabilities.
Kazuhiko Nishioka
Kazuhiko Nishioka is the co-founder and CEO of Sun Metalon, a Japan-origin, Chicago-area climate-tech company decarbonizing the metal industry. A former Nippon Steel engineer with a materials science background from Northwestern University, he built a patented, near zero-emission heating technology that turns metal scrap, sludge and swarf into clean, reusable metal pucks on-site. Founded in 2021, Sun Metalon has raised roughly $42M in total funding, partnered with Toyota on aluminum recycling, and drawn Nippon Steel's first venture investment in its 100-plus-year history.
Nihal Advani
Nihal Advani is the founder and CEO of QualSights, a Chicago-based insights technology platform that helps global brands decode real-world human behavior through live video, mobile ethnography, sensors and AI. A former internationally ranked junior tennis player from India who came to the US on a full scholarship, he cut his teeth at Google and Microsoft before founding the travel startup Georama in 2012, then pivoting it into QualSights in 2018. On roughly $3.5M raised over a decade, he built one of America's fastest growing market research companies, ranked by Inc. as the fastest growing company in Illinois.
Jan Seale
Jan Seale is the CEO and co-founder of Out of Office, a Chicago-based travel app that turns recommendations from your own friends and trusted circle into bookable trips across thousands of cities. A Cornell grad who spent years at Gap, Trunk Club, and Havenly before building her own company, she launched a travel startup in the middle of a global pandemic - and became one of the first 100 Black women in the United States to raise more than a million dollars in venture capital. She runs on gratitude, literally: she starts every morning by naming ten things she is grateful for.
Alex Kelleher
Alex Kelleher is the founder and CEO of Quantum Rise, a Chicago AI consulting startup that raised a $15M seed in 2024 to pursue what he calls 'Consulting 2.0' - replacing billable-hours advice with heavy engineering and automation for mid-market companies. An Oxford-trained experimental psychologist, he has founded four data and decisioning software companies, with exits including Touch Clarity (to Omniture/Adobe), Cognitive Match (to Magnetic), and Vivid Edge. He went on to serve as Global CMO at Deloitte Digital and Chief Data Officer / President of Intelligence at Advantage Solutions. He is also a TED Global speaker and an exhibited artist.
Andrew Rowland
Andrew Rowland is the founder and CEO of Classkick, a Chicago-based education technology company whose real-time digital notebook lets teachers see every student's work as it happens and respond instantly with notes, audio, or chat. A former Chicago high-school math teacher known to his students as 'Mr. Roro,' Rowland taught through Teach for America and started a school robotics program before retraining in computer science and working at Google and YouTube. He built Classkick to scale the thing he loved most about teaching: the 'aha' moment and the fast feedback loop. The platform now reaches more than half of U.S. schools and students in 180-plus countries, running on Firebase infrastructure.
Anj Fayemi
Anj Fayemi is a Lagos-raised, MIT-trained mechanical engineer and recording rapper (Solstice Fayemz) who turned his own frustration releasing a second album into Rivet, an AI-driven CRM that helps artists and creators find and grow their most loyal fans. As co-founder and CEO, he interviewed 200+ artists, went through Techstars Boston, raised a $500k pre-seed led by Drive Capital, and built a platform used by roughly 1,400 creators that stitches together data from Instagram, Shopify and Eventbrite to surface the fans most likely to show up and buy.
Chris Foreman
Chris Foreman is the co-founder and CEO of Marketplace.city, a Chicago-based govtech platform that helps local governments find, validate, and buy new technology with the help of real pricing, contract, and outcome data. Before building Marketplace.city, he scaled AvePoint's Americas business from a small team to more than 1,200 employees across 15 countries and launched its public-sector subsidiary, where the company won three straight Microsoft Partner of the Year awards. A Northwestern political science graduate, he has spent 15-plus years in enterprise software and now spends his days trying to drag government buying out of the PDF era.
Dan Schuleman
Dan Schuleman is the co-founder and CEO of Qumis, a Chicago-based AI platform that reads and interprets complex insurance policies the way a seasoned coverage attorney would. A former insurance coverage litigator and in-house counsel at Kin Insurance, he started Qumis in 2023 after years of marking up dense policy PDFs by hand. The company has raised roughly $6.75M and counts five of the 15 largest U.S. insurance brokers among its users.
Hami Babai
Hami Babai is the founder and CEO of Power Kiosk, a Chicago-based cloud platform that turned the messy, paper-heavy world of energy procurement into an online marketplace connecting brokers, suppliers, and customers. An Iranian immigrant who landed in Chicago at 21 with $4,000 and no credit, he earned a Ph.D. in engineering from Northwestern, bootstrapped Power Kiosk for roughly four years, and grew it into one of North America's largest energy brokerage platforms - licensed across dozens of states and provinces and credited with returning well over $100 million in savings to customers.
Marc Gyoengyoesi
Marc Gyoengyoesi is the founder and CEO of OneTrack.AI, a Chicago company that puts AI cameras on forklifts to give warehouses the kind of real-time visibility that factory floors take for granted. He started out building autonomous inventory drones at Northwestern's startup incubator as Intelligent Flying Machines, crashed one on stage at TechCrunch Disrupt in front of 2,500 people, picked up 12 stitches from another crash in development, and concluded that the cameras mattered more than the things flying them. Today OneTrack runs on deep learning, computer vision and distributed computing across trillions of images, turning forklift footage into safety alerts, shipment validation and operational intelligence.
Matthew Shaxted
Matthew Shaxted is the founder and CEO of Parallel Works, a Chicago company that turns the headache of running heavy AI, machine learning, and simulation workloads across clouds and on-premises systems into a single control plane. A civil engineer who once wired 30 Linux desktops into a render farm to push building simulations, he met co-founder Michael Wilde at Argonne National Laboratory and spun the lab's parallel-workflow technology into a company in 2015. Bootstrapped and cash-flow positive, Parallel Works now powers hurricane risk models, cancer research, space-weather digital twins, and IL5-authorized defense workloads.
Sheri Rudberg
Sheri Rudberg is the co-founder and CEO of WovenX Health, a Chicago-based digital health company that pairs specialty-trained virtual care teams with an AI-native platform to fix the brutal wait times patients face for gastroenterology and other specialty care. A lawyer and operator by training - Georgetown Law, a Northwestern MBA, and years running a $100M business at Hillrom - she started the company (originally Telebelly Health) after watching her own family struggle to get specialist appointments. WovenX partners with brick-and-mortar practices and health systems rather than competing with them, aiming to turn months-long backlogs into care delivered in minutes.
Alex Niemczewski
Alex Niemczewski is the co-founder and CEO of BallotReady, the nonpartisan online voter guide that covers every race and referendum on the ballot across all 50 states. She built the first version for herself before the 2014 midterms because she didn't know how to vote for the down-ballot offices nobody talks about - water reclamation commissioner, judges, mosquito abatement boards. A University of Chicago philosophy graduate who taught coding and ran a research-design consultancy, she turned a personal frustration into a civic engagement platform that informs millions of voters and powers tools for campaigns and advocacy groups.
Ali Akhtar
Ali Akhtar is the co-founder and CEO of Letter AI, a Chicago-based, AI-native revenue enablement platform that helps B2B sales teams build training, content, coaching, and live deal guidance with generative AI. A University of Chicago and Michigan Ross graduate, he spent roughly a decade leading machine learning and product teams at Samsara, project44, and McKinsey before launching Letter AI through Y Combinator's Summer 2023 batch. By early 2026 the company had raised more than $52 million, including a $40 million Series B led by Battery Ventures, and counted Lenovo, Adobe, Novo Nordisk, Plaid, and SolarWinds among its customers.
Andy Feis
Andy Feis is the co-founder and CEO of Renterra, a Chicago-based company building a cloud-based operating system for the equipment rental industry. A Stanford-trained engineer and former Bain & Company consultant, Feis launched Renterra in 2022 with co-founder Nick Hibberd to modernize a sector that runs construction, infrastructure, and local economies but had long been underserved by software. By early 2026 the platform served hundreds of rental companies across the U.S. and Canada, processing hundreds of millions in annual rental transactions, and raised a $9M Series A led by Avenue Growth Partners, bringing total funding to roughly $16M.
Lewis Burik
Lewis Burik is the co-founder and CEO of DubClub, a Chicago-based platform that connects amateur sports bettors with vetted professional handicappers, or 'cappers,' through subscriptions delivered by text, email, and Discord. A former Stanford inside linebacker who walked on to the Cardinal, Burik started DubClub in 2021 with two college teammates after watching a friend struggle to find trustworthy betting picks online. The company has since grown to roughly 1.5 million fans, crossed $95M+ in lifetime GMV, and raised a $7.5M Series A led by Renegade Partners in 2024, turning a fragmented corner of the creator economy into a profitable marketplace.