Influential Chicago Software Startups Redefining Tech Industry in 2023

Chicago, Illinois, known as the Windy City and the birthplace of the skyscraper, has more than just deep-dish pizza and dynamic architecture to boast. Over the past decade, the city has evolved into a thriving tech hub, home to a growing community of innovative software startups. From cybersecurity to e-commerce, edtech to fintech, these trend-setting firms are putting Chi-town on the map in the global tech scene. Let’s explore some software startups originating from this vibrant city.


Founded by Dan Pinto and Valentin Vasilyev, Fingerprint is leading the charge in online fraud detection through cybersecurity, IT, and software technology. This ambitious startup empowers developers to combat internet fraud directly, offering a robust solution to a pervasive issue.


Positioning itself at the intersection of cybersecurity and developers’ platforms, oak9 provides a SaaS platform that ensures cyber-secure software development. Aakash Shah, Om Vyas, and Raj Datta reside at the helm of the company, safeguarding software development in the digital age.


Transforming the way data centers and bare metal equipment are managed is MetalSoft. Their distinctive automation software platform streamlines the management process, enabling businesses to focus on their core functionalities.


Disrupting the property tech scene is taxProper. Co-founded by Geoff Segal and Thomas Dowling, taxProper provides homeowners with a platform to effectively manage and potentially reduce their property taxes.


Breaking new ground in advertising, Fyllo offers innovative marketing and regulatory solutions powered by the cloud. Founded by Aristotle Loumis, Chad Bronstein, and Erik Shani, Fyllo caters notably to the cannabis industry, handling compliance and enterprise software for burgeoning businesses.

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Revolutionizing e-commerce through 3D technology and augmented reality (AR) is levAR. Its founders, Daniel Esrig, Tre Lucas, and Tyler Blake, are implementing their novel platform to help e-commerce businesses thrive in an increasingly digital market.


TeleTeachers, founded by Emily Smith, spotlights online learning specializing in speech-language pathology. Their innovative software makes it possible for more advances in e-learning and speech recognition.


Key is a fan relationship platform redefining talent management through brand marketing and data visualization. Evan Wayne and Stephanie Biegel founded this unique startup, integrating digital marketing, payments, and SaaS into one platform.


Founded by Mike Matker, SiteVibes is a shopper experience platform optimizing e-commerce businesses’ growth through social media marketing and digital media strategies.

DevX School

Serving as a launchpad for new software engineers is the e-learning platform – DevX School. This edtech startup opens a gateway for those with zero coding background to break into the industry.

Broadleaf Software

Broadleaf Software, led by Alex Leonowicz, is working with cannabis companies on streamlining their operations. The startup provides software solutions that enhance efficiency and product quality.


TrustClarity, owned by Hakki Unuvar and Sujee Jeganathan, is a B2B SaaS storefront platform redefining the traditional online business models.

Sav, helmed by Anthos Chrysanthou, provides industry-leading solutions such as DNS, SSL, CDN, Email Forwarding & Domain Forwarding, among others, and sells more than just domains.


Transforming project management and social networking is Frank. Co-founders Charlie Aufmann and Mary Urbina- McCarthy have created a platform that encourages worker voice and collective action.

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Last on the list but certainly not least, is TimeTraveler. Founded by Daniel Y. Chung, this startup is breaking barriers in virtual reality, offering innovative hardware and software for the consumer electronics market.

From finance to education, real estate to retail, these trailblazers are harnessing the power of software to solve complex problems and create value in the new digital era. As Chicago’s ecosystem of innovative startups continues to thrive and expand, one can only imagine what the Windy City’s tech future holds.

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