chicago-startup
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FoodBoss Built Kayak for Takeout - Then Google Walked Into the Kitchen
The Chicago startup made delivery apps compete on price and speed, then learned the harder lesson of comparison businesses: the better your idea works, the more likely a platform giant is to copy the view.
The Chicago Startup That Wants to Make Waiting for Money Feel as Weird as Waiting for a Fax
Daniel Lev and Benjamin Meeder built a payment layer on stablecoins instead of the batch files banks still run on. Two years in, Pantera wrote a $25M check and revenue is up 23x.
The Startup That Turned the Office Supply Closet Into Software
Kathryn Madden built OfficeLuv around a boring truth: someone always ends up ordering the paper towels. Her bet was that the someone should be software - plus a person who shows up.
The Startup That Turned Dinner Into a Barcode
A smart oven, a weekly box of meals, and one deceptively simple idea: let a barcode do the cooking. Here is how a University of Chicago class project shipped 40 million dinners.
The Chicago lab teaching hospitals to read your blood before sepsis reads you
Sepsis kills more Americans than all cancers combined and hides in plain sight. Prenosis spent a decade building a biobank and an algorithm to catch it in the first 24 hours - and got the FDA to say yes.
The Borrowed Cadillac That Became an Office-Pantry Empire
Crafty began with four friends, a borrowed Cadillac, and a plan to put a kegerator in every office. A decade later it stocks the snacks for DraftKings and Robinhood - and turns the break room into a spreadsheet.
The Yellowstone Microbe That Wants Your Breakfast Table
A geomicrobiologist scooped a strange fungus out of a Yellowstone hot spring. A decade and half a billion dollars later, it is being sold as cream cheese, yogurt and breakfast patties.
CoinFlip
It started with one machine in a Chicago restaurant and no outside money. A decade later CoinFlip runs the world's largest crypto ATM network - and it built the whole thing before anyone offered to fund it.
Paro
Paro is a Chicago-based, AI-powered marketplace that connects businesses and accounting firms with vetted fractional finance and accounting experts - from bookkeepers and controllers to fractional CFOs. Founded in 2015, it pairs its proprietary matching algorithms across 60+ industries and 250+ skill sets with data tools and advisory insight, aiming to become the go-to resource for finance and accounting solutions as the profession faces a deepening talent shortage.
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.
Amper Technologies
Amper Technologies is a Chicago-based industrial IoT company that helps manufacturers see and improve what happens on their shop floors in real time. Its FactoryOS platform pairs non-invasive sensors that clip onto any machine - regardless of age or brand and install in about ten minutes - with AI-driven analytics that track machine utilization, OEE, downtime, labor and job performance. Founded in 2016, Amper turns legacy factory equipment into a source of live production data without expensive retrofits or complex IT integrations, and was acquired by ECI Software Solutions in December 2025.
Benji
Benji is the universal API for loyalty partnerships - think 'Plaid for loyalty rewards.' It lets brands across travel, hospitality, retail, food and fintech connect their loyalty programs through a single integration, launching co-branded earn, redemption, transfer and co-acquisition campaigns in days instead of months. Founded by the serial team behind 2ndKitchen (acquired by REEF Technology in 2021), Benji raised a $6.25M seed round in 2026 and already powers a network of programs - including JetBlue, CookUnity, 1-800-Flowers and Chip City - representing more than 50 million combined active members.
Classkick
Classkick is a Chicago-based education technology company that makes a digital formative-assessment platform where teachers watch students work in real time and give instant feedback. Founded by former Teach for America math teacher and ex-Google/YouTube engineer Andrew Rowland, the tool lets teachers build or import interactive assignments, draw directly on each student's canvas, drop reusable feedback stickers, and auto-grade multiple-choice and fill-in-the-blank answers. Students can raise a virtual hand for help - even anonymously - and ask peers. Used by more than 10 million users across all 50 U.S. states and dozens of countries, Classkick's pitch is simple: more tries for kids every day, and less grading busywork for teachers.
Marketplace.city
Marketplace.city is a Chicago-based govtech company that helps state and local governments source, validate, and procure technology. Its Clearbox platform turns a repository of historical vendor, contract, and pricing data into managed procurement services (Clearbox Procure) and a research subscription (Clearbox Source), aiming to compress technology buying cycles that once ran months or years down to roughly 100 days. Founded out of a 2016 collaboration with New York City's Mayor's Office of Technology and Innovation, the company has supported over 200 governments.
Out of Office
Out of Office (OOO) is a Chicago-based travel technology company that helps people plan trips using recommendations from the people they actually trust - friends, family, and the influencers they follow - instead of anonymous review sites. Founded in 2020 by former Trunk Club executives Jan Seale and Coabi Kastan, the app lets travelers browse curated spots across thousands of cities, build and share itineraries, book hotels, and reserve restaurant tables in one place, and more recently generate full trip plans with an AI trip generator.
Parallel Works
Parallel Works is a Chicago-based software company, spun out of Argonne National Laboratory in 2015, that builds ACTIVATE - a hybrid multi-cloud control plane for high-performance computing and AI. The platform gives researchers, engineers and defense teams a single interface to provision, orchestrate and share compute across on-premises clusters and the major clouds (AWS, Azure, Google Cloud, Oracle), with built-in cost governance, role-based access and security controls. In 2025 ACTIVATE's High Security Platform became the first hybrid multi-cloud solution to earn a U.S. Department of Defense IL5 Authority to Operate.
Power Kiosk
Power Kiosk is a Chicago-based SaaS company that runs a cloud-based marketplace connecting retail energy suppliers with the brokers and consultants who buy electricity and natural gas on behalf of businesses. Founded by Northwestern Ph.D. Hamed Babai, the platform pulls fragmented supplier rates, contracts, and market data into one AI-assisted workflow so brokers can quote, compare, and close deals in minutes instead of days. The company says it has managed 16,000+ customers across 34 states and provinces and returned roughly $120 million in savings.
Quantum Rise
Quantum Rise is a Chicago-based AI transformation company founded in 2024 by serial entrepreneur Alex Kelleher. It sells what it calls 'Consulting 2.0' - a products-not-projects model that pairs an enterprise AI operating system (QR/OS), a repeatable methodology, and forward-deployed experts to help mid-market and enterprise clients turn AI into measurable revenue and cost savings. Backed by a $15M seed round from Erie Street Growth Partners, the company argues the traditional billable-hours consulting model is about to collapse under automation, and it aims to fill the gap between the Big Four giants and smaller boutique shops.
Qumis
Qumis is a Chicago-based insurtech building attorney-trained AI for commercial insurance. Its coverage intelligence platform reads dense property and casualty policies the way a seasoned coverage attorney would - comparing quotes and endorsements, flagging gaps across policy towers, and backing every answer with source-linked citations and transparent reasoning. Founded by a former coverage attorney and a former Goldman Sachs engineering leader, Qumis already serves five of the 15 largest U.S. brokers, along with specialty carriers and insurance law firms, and has raised $6.75M to put a coverage specialist at every desk.
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.