The Top 25 Tech CEOs of Chicago for 2024

Key Executives is pleased to announce The Top 25 Tech CEOs of Chicago for 2024. Chicago has emerged as one of America’s leading tech hubs, with an impressive 18% growth in its tech workforce over the past decade. Unlike the overall economy, which grew by just 1%, the tech sector has shown remarkable resilience, playing a crucial role in supporting Chicago’s recovery during the COVID-19 pandemic. The sector's growth is fueled not only by new startups but also by the integration of technology across various industries, including government, healthcare, and Fortune 500 companies.

This year’s awardees are influential leaders within Chicago's tech workforce of over 100,000, generating hundreds of millions of dollars in revenue. From executives leading the charge in technological innovation and cloud-based solutions to those steering advancements in supply chain management and education technology, these CEOs exemplify the diverse capabilities that propel Chicago's tech-driven economy. Their strategic vision and commitment to operational excellence not only advance their organizations but also strengthen Chicago's position as a vital hub for technological advancement and entrepreneurship.

Among this year’s awardees, Kelsey Behringer, Chief Executive Officer of Packback, is recognized for her innovative approach in leveraging AI to enhance educational experiences, providing real-time feedback to students and empowering educators across over 600 institutions. Carlo Passacantado, Chief Executive Officer of Fuel Me, stands out for his entrepreneurial vision in the energy sector, having developed a cloud-based platform that optimizes fuel procurement processes. Additionally, Jeff Furman, Chief Executive Officer of CareerBuilder, is acknowledged for his leadership in transforming talent acquisition solutions, helping businesses streamline hiring processes while enabling job seekers to advance their careers.

This year’s awardees were selected through a methodical nomination process and careful consideration of each candidate’s career track record and industry contributions. Please join us in celebrating The Top 25 Tech CEOs of Chicago for 2024.

 

1. Taylor Rhodes
Chief Executive Officer, Applied Systems

Taylor Rhodes is the Chief Executive Officer of Applied Systems, a global provider of cloud-based software that powers the business of insurance. Recognized as a pioneer in insurance automation and the innovation leader, Applied is the world’s largest provider of agency and brokerage management systems, serving customers throughout the United States, Canada, the Republic of Ireland, and the United Kingdom. Rhodes leads Team Applied and is responsible for the company's overall strategy and operational execution. 

Rhodes joined Applied in 2019 after serving as CEO of SMS Assist, a cloud-based software platform for multi-site property management. Previously, he was CEO of Rackspace, where he led the company’s growth from a cloud pioneer to an industry leader with more than $2 billion in revenue. Prior to Rackspace, he served as a leader in enterprise, financial, and corporate strategy roles at Electronic Data Systems Corporation. Rhodes is a former United States Marine Corps infantry officer and holds a MBA from the University of North Carolina at Chapel Hill.

 

2. Tom Kilroy
Chief Executive Officer, Keyloop

Tom Kilroy is the Chief Executive Officer of Keyloop, where he is responsible for the company’s strategic direction and growth. Keyloop is a leading provider of automotive retail solutions, with more than 40 years of industry expertise and over 14 billion digital interactions captured to date. The company provides solutions that support various stages of the automotive retail ecosystem, connecting retailers, OEMs, financiers, and fleet suppliers with consumers through Experience-First software.

Prior to joining Keyloop, Kilroy was an Operating Partner at Francisco Partners Consulting. Before that, he spent 10 years as the Chief Operating Officer of Finastra, a fintech software company. There, Kilroy held various roles in which he was responsible for driving growth and profitability. In 2012, as Interim CEO, Kilroy led the take-private of Misys plc. He later led the integration of Misys and D+H. Prior to that, Kilroy spent eight years at GE Healthcare, a division of General Electric. Kilroy graduated from the University of Oxford with a master’s degree and undergraduate degree in metallurgy and materials science.

 

3. Jeff Furman
Chief Executive Officer, Careerbuilder

Jeff Furman is the Chief Executive Officer of Careerbuilder. With over 25 years in the industry, CareerBuilder operates as a global talent marketplace, offering solutions to assist employers in finding, hiring, and onboarding talent, while helping job seekers develop skills and advance their careers in the evolving job market. Furman is a business executive with over three decades of corporate leadership experience.

Furman is responsible for all aspects of the CareerBuilder business and operations. He joined CareerBuilder in January 2018 as Vice President and was charged with reducing the company’s cost structure and speeding its return to growth. During his tenure, he has brought significant value through his leadership in managing costs, business divestitures, and as a member of the executive leadership team.

Prior to CareerBuilder, Furman led Fortune 100 and 500 corporate operating functions for American Express and Tyco International/Johnson Controls. He had a 20-year career at American Express, leading multiple large operating functions. He also spent three years with Tyco in similar roles, supporting customer and strategic objectives while also working on the company’s executive transition team for the merger with Johnson Controls. Furman holds a bachelor’s degree in architecture from the Illinois Institute of Technology.

 

4. Sheryl Hoskins
Chief Executive Officer, Litera

As Chief Executive Officer, Sheryl Hoskins is responsible for leading Litera as it scales its enterprise software businesses, delivers the best legal technology ecosystem, and revolutionizes how legal teams and law firms use technology to drive digital transformation. Litera has been at the forefront of legal technology innovation for over 25 years, crafting legal software to amplify impact and maximize efficiency.

Hoskins has more than twenty years of experience in the global technology industry and a proven track record managing global teams. She spent the first decade of her career at General Electric and McKesson Corp, where she held domestic and international leadership roles. Most recently, Hoskins served as CEO of Upserve. Hoskins received a BS Degree in Electrical Engineering, an MBA in Marketing, and is a US Army veteran.

 

5. Shaily Baranwal
CEO and Founder, Elevate K-12

Shaily Baranwal is the Founder and Chief Executive Officer of Elevate K-12, a Chicago-based live teaching company that brings high-quality live teaching to K-12 classrooms. Schools and districts partner with Elevate K-12 to help solve their teacher shortage challenges and provide effective and engaging instruction to their students. Before Elevate K-12, Baranwal founded two other companies, including a chain of preschools for low-income students in rural India, and is a former classroom teacher herself.

Previously, Baranwal was a Founder and CEO at Urban Foods and before that a Founder and CEO at Jr Einsteins Pre-Schools. Earlier in her career she worked with AT Kearney as a management consultant. Baranwal has degrees in industrial engineering, early childhood education, and an MBA from the University of Michigan. Baranwal serves on the boards of the University of Michigan Zell Lurie Institute and the University of Michigan Ross School of Business.

 

6. Jett McCandless
Founder and CEO, Project44

Jett McCandless is Founder and CEO of project44, a high-velocity supply chain platform. Under McCandless’ leadership, project44 has grown into a $2.7 billion company that tracks over one billion shipments annually in more than 185 countries for over 1,300 leading brands. The company generates more than $100 million in annual recurring revenue and is recognized as a significant player in the logistics technology sector.

An entrepreneur with over 20 years of transportation and logistics experience, McCandless has guided multiple early-stage companies from ideation, startup, and expansion through to maturity. He previously founded Metafora, an advisory firm formerly known as CarrierDirect, which was listed on the Inc. 500. He sold his stake in GlobalTranz, a third-party logistics company valued at over $2 billion, where he served as Executive Vice President and Principal.

 

7. Simon Angove
Chief Executive Officer, Syndigo

Simon Angove is the Chief Executive Officer of Syndigo, a cloud-native platform specializing in content management and data solutions to enhance experiences across organizations, domains, and customers. Angove has over 25 years of leadership experience in technology, having both launched start-ups and run large companies and divisions in industries such as retail, financial services, and the public sector.

Previously, Angove served as CEO of Superion, a software provider to the local government. There, Angove led a comprehensive transformation establishing product innovation, go-to-market execution, and operational excellence. His leadership contributed to a multi-company merger that established CentralSquare.

Before Superion, Angove led global business units at Verint, an omni-channel customer engagement software provider, and was a serial entrepreneur starting companies in cloud computing, retail in-store video analytics, and workforce optimization. Angove graduated from Boston College with an undergraduate degree in general management.

 

8. Oakleigh Thorne
CEO and Chairman, Gogo

Oakleigh Thorne currently serves as President and Chief Executive Officer of Gogo, a leading provider of broadband connectivity services for the business aviation market. Gogo offers a customizable suite of smart cabin systems for highly integrated connectivity, inflight entertainment, and voice solutions.

Thorne has approximately 30 years of leadership experience with significant operational and financial expertise. Prior to joining Gogo, he was the Chief Executive Officer of Thorndale Farm LLC. He has served in numerous senior management positions, including as Chief Executive Officer of eCollege.com and Commerce Clearing House. He holds an MBA in accounting and finance from Columbia Business School and a bachelor’s degree in journalism from Boston University.

 

9. Morgan Kurk
CEO and President, Cambium Networks

Morgan Kurk is the President and Chief Executive Officer of Cambium Networks and serves on the board of directors. Cambium Networks enables service providers, enterprises, industrial organizations, and governments to deliver exceptional digital experiences and device connectivity with compelling economics.

Previously, Kurk served as President of Personal Protection Equipment at Honeywell International. Before that, he held various positions including VP of Enterprise Segment, VP of Wireless Segment, VP of Broadband Segment, Chief Technology Officer, and Chief Operations Officer and Executive Vice President at CommScope. Kurk holds an MBA from Northwestern University, a master’s degree in electromagnetics and optics from the University of Michigan, and a bachelor’s degree in electromagnetics from Brown University.

 

10. Ted Elliott
Chief Executive Officer, Copado

Ted Elliott is the Chief Executive Officer of Copado, which specializes in AI-powered DevOps for business applications. The company supports over 1,750 global brands, including Coca-Cola, Medtronic, T-Mobile, and Volkswagen, by improving development workflows through advanced AI capabilities.

Before joining Copado, Elliott spent 18 years as the CEO of Jobscience, one of the first five ISV partners to Salesforce, until the company’s acquisition by Bullhorn. Elliott graduated from the University of San Francisco School of Law with a JD in corporate law and from Washington and Lee University with an undergraduate degree in history.

 

11. Brad Weisberg
Founder and CEO, Snapsheet

Brad Weisberg is the Founder, Chief Executive Officer, and Chairman of the Board of Snapsheet. Snapsheet provides a claims solution designed to adapt to business needs. The company partners with over 150 organizations, including 16 of the top 20 property and casualty insurance carriers, to streamline claims, appraisals, and payment processes. 

Since its founding in 2011, Weisberg has guided Snapsheet through various growth phases. He focuses on addressing complex challenges with efficient technical platforms while directing all aspects of development and operations. Weisberg holds a bachelor’s degree in marketing and advertising from Indiana University Bloomington and is a guest lecturer at Northwestern University.

 

12. Peter Granat
Chief Executive Officer, SAI360

Peter Granat is the Chief Executive Officer of SAI360, where he leads a global team that provides integrated solutions for ethics, governance, risk and compliance software, and online training. SAI360 supports businesses with risk management, trust-building, and business resilience. With more than 25 years of experience in executive management, B2B SaaS platforms, and M&A, Granat has a track record of driving profitable growth for PE-backed companies, building strong leadership teams, and creating value for clients and stakeholders. 

Previously, Granat was a group CEO at SAI Global and before that a group CEO at Cision. Earlier in his career he worked with MediaMap, Inc. as a Senior Vice President. Granat holds an MBA from the Northwestern Kellogg School of Management and a bachelor’s degree from the University of Vermont.

 

13. Kelsey Behringer
Chief Executive Officer, Packback

Kelsey Behringer is the Chief Executive Officer of Packback, an organization that has trained over 10,000 educators on the intersection of AI and pedagogy. Packback provides an AI writing tutor for students and an AI grading assistant for teachers, helping to implement best practices that enhance student voice, agency, and purpose. Behringer joined Packback in 2017 and has held various roles within the organization, including educator trainer, manager, director, Vice President, and Chief Operating Officer before becoming CEO.

The AI technology developed by Packback has been utilized by over two million students across 600 colleges and school districts, providing instant, real-time feedback to help students develop their unique voices in writing. Behringer's approach is informed by her experiences as a former STEM teacher in Chicago and Indianapolis. She is a Fast Company Executive Board contributor and hosts monthly webinars for teachers and professors, offering insights and recommendations on AI in education.

 

14. Margi Shaw
Chief Executive Officer, Nitel

Margi Shaw is the Chief Executive Officer of Nitel, where she leads the company in its next phase of growth. She focuses on implementing customer solutions while prioritizing reliable, customer-centric service models. Shaw is attuned to customer needs and aims to align Nitel’s growth strategies with those demands. Nitel is a next-generation technology services provider that addresses the complex technology challenges faced by enterprise organizations, creating integrated managed network solutions.

Throughout her career, Shaw has demonstrated the ability to lead high growth technology companies by balancing strategy and innovation with customer-centric operations. She brings over 30 years of technology and leadership experience to Nitel, most recently serving as the president and CEO of First Communications, LLC. Shaw also served as COO at CIMCO Communications, leading growth and transformation for nearly a decade. Following the strategic acquisition of CIMCO by Comcast, Shaw led the team through the complex process of integration. Shaw graduated from Bowling Green State University.

 

15. Yushiro Kato
CEO and Co-Founder, CADDi

16. Carlo Passacantado
Chief Executive Officer, Fuel Me

Carlso Passacantado is the Chief Executive Officer of Fuel Me, a cloud-based platform that enables customers nationwide to purchase energy commodities for trucks, machinery, generators, or tanks. Fuel Me completed a Series A funding round in 2024 and is currently collaborating with several Fortune 500 companies to optimize operations and administrative processes in the fuel procurement industry.

Passacantado began his entrepreneurial journey as a freshman at Columbia University, where he founded a laundry pick-up and delivery service for students. This venture rapidly expanded and, by his junior year, he acquired DormAid, the nation’s largest college service provider, servicing over 1,000 campuses nationwide.

After graduating, Passacantado became a Partner and President at Timo Weiland, a clothing company that grew to over 300 stores globally, leveraging licensing partnerships with major retailers and brands, including Banana Republic, Urban Outfitters, Intermix, Champion, and Swarovski.

Passacantado also founded several energy technology companies, including ThermAdynamics Rail, which develops waste heat recovery systems for combustion engines, Entropea Labs, focused on stationary waste heat recovery systems, and Holosgen, which is working on a micro-modular nuclear generator funded by the Department of Energy.

Carlo Passacantado's Insights

“The key to success is the ability to find the simplest solutions to solve complex problems, continuously innovating in order to make sure that you are evolving based on the needs of the market, and to do all this without ever becoming overwhelmed, maintaining calmness and composure while facing any unexpected challenge.”

 

17. Raleigh McClayton
CEO and Board, Brightspot

Raleigh McClayton is the Chief Executive Officer and a board member of Brightspot. Brightspot provides modern content teams with a platform designed to efficiently create and share content, offering speed, customizability, ease of use, and access to expertise. McClayton brings over a decade of experience leading both B2B and B2C software and technology firms. He is dedicated to collaborating with talented teams to develop high-quality digital products.

Previously, McClayton served as CEO of ArrowStream, a supply-chain software business that achieved significant growth before being acquired in 2022. Prior to ArrowStream, he served as President of LoopNet, an advertising platform for commercial real estate. Earlier in his career, he served as Head of Digital Marketing and Strategy for Restaurant Brands International, overseeing the digital growth of leading restaurant brands. McClayton holds an MBA from the University of Chicago and a bachelor’s degree in economics and East Asian studies from Davidson College.

 

18. Martin Franchi
Chief Executive Officer, NinjaTrader

Martin Franchi is the Chief Executive Officer of NinjaTraderwhich provides trading software and brokerage services to active futures traders. Founded in 2003, NinjaTrader has become an industry leader, supporting over 1 million traders globally with technology, competitive commissions, and comprehensive support. Franchi is an executive leader with a track record of success creating value through leadership of multiple business functions, entities, and strategy execution. 

Franchi's experience encompasses various roles across multi-billion-dollar conglomerates and emerging start-ups. Throughout his career, he has participated in transformative projects, including raising equity for a developing start-up, managing the divestiture of operating companies, and overseeing the successful merger of multiple entities.

Previously, Franchi held various finance and accounting positions at Kraft Foods. He later served as Finance Director at BigTick. He played a key role in the acquisition of Mirus Futures by NinjaTrader Group and was subsequently promoted to Chief Operating Officer, adding business operations responsibilities to his previous role as Chief Financial Officer. Franchi later advanced to Chief Executive Officer, overseeing all business entities, products and services, and business functions. He graduated from Illinois State University with a degree in finance.

 

19. Anita Samojednik
Chief Executive Officer, Paro

Anita Samojednik is the Chief Executive Officer of Paro, a company specializing in connecting businesses with finance professionals. Paro’s platform facilitates the integration of financial expertise into organizations, allowing companies to efficiently manage their finance and accounting functions. Samojednik brings 21 years of experience to her current role. Since joining Paro, Samojednik has leveraged artificial intelligence to redirect the company’s focus to investments that drive predictable growth while leading integrated operations as the company scales.

Before joining Paro, Samojednik was a President at Groupon International and before that a VP of Customer Operations at Ladders. Earlier in her career she worked with EasyLink as a customer care director. Samojednik graduated from Columbia Business School with an MBA in management operations, from London Business School with an MBA in operations and from The New School with an undergraduate degree in psychology.

 

20. Candice Xie
Co-Founder and CEO, Veo

Candice Xie is the Co-Founder and CEO of Veo, a micro-mobility company operating electric scooters and bikes in cities and universities. The company designs and engineers vehicles, hardware, and software systems to provide a greener, healthier mode of transportation, aiming to make communities more sustainable and livable.

Xie brings eight years of experience to her current role and first got her start in 2016 as a finance advanced development program associate at Schneider Electric, her most recent position prior to joining Veo. Xie graduated from the University of Chicago with an MBA and from Purdue University with an undergraduate degree in finance.

 

21. Rob Holland
Chief Executive Officer, RedShelf

Rob Holland is the Chief Executive Officer of RedShelf. Founded in Chicago in 2012, RedShelf aims to transform traditional learning materials for over 10,000 publishers and deliver digital content to millions of learners at over 1,800 institutions and businesses. Holland has a strong track record as an entrepreneur and C-level executive in high growth companies. He has successfully driven growth at venture-backed startup companies and private equity-backed businesses ranging from $10 to $750 million in sales. 

Most recently, Holland served as CEO of Feedback Loop, a unified market intelligence platform that was acquired by DISQO Inc. He has successfully built businesses and grown companies valued at over $1 billion, including Bluecore Inc. and Datalogix, which was acquired by Oracle. Holland has also held leadership positions in product management at The Nielsen Company. Holland graduated from San Diego State University with an undergraduate degree in business administration.

 

22. Ed Scanlan
Chief Executive Officer, Bridge Legal

Ed Scanlan is the Chief Executive Officer of Bridge Legal, a cloud platform designed to power the end-to-end client journey for those who have been injured and harmed. The platform equips law firm clients with tools powered by AI, automation, analytics, and workflow to advocate for the rights of everyday individuals. 

Bridge Legal aims to provide the resources that plaintiff attorneys need to effectively represent their clients and hold corporations accountable for the harm they cause. Previously, Scanlan founded Total Attorneys in 2002. He successfully bootstrapped Total Attorneys to achieve over $30 million in annual revenue, serving as its founding CEO for ten years.

 

23. Loukeek Bornare
Chief Executive Officer, Tulfa Inc.

Loukeek Bornare is the Chief Executive Officer of Tulfa Inc., an American multinational corporation that designs and develops e-commerce shopping solutions for brands, retailers, and manufacturers. Headquartered in Chicago, Illinois, the company has helped several Fortune 500 companies provide an advanced shopping experience using augmented and extended reality. Bornare is a senior executive leader with a track record of producing sustained revenue and accelerated EBITDA growth in dynamic markets. 

Previously, Bornare was a director of business solutions at Iksula and before that a director of business solutions at Infinite Computing Systems. Earlier in his career he worked with Intelliswift Software, Inc. as a senior manager of business development. Bornare earned a master’s degree in information technology from DG Ruparel College of Arts, Science and Commerce and an undergraduate degree in information technology from St. Andrew's College of Arts, Science and Commerce.

 

24. Baber Abbas
Chief Executive Officer, viaPhoton

Baber Abbas is the Chief Executive Officer of viaPhoton, a fiber solutions provider specializing in end-to-end connectivity. The company adopts a customer-first approach and leverages advanced technology to manufacture its products in the United States. Abbas has been instrumental in steering viaPhoton's growth and innovation in the fiber connectivity market.

Abbas brings 21 years of experience to his current role. Before joining viaPhoton, he was a director of the product line at CommScope. Earlier in his career he worked with Andrew Corporation a CommScope Company as a technical sales engineer. Abbas graduated from The University of Chicago Booth School of Business with an MBA in strategic, general management, finance, and entrepreneurship, from Virginia Tech with a master’s degree in finance, and from Ghulam Ishaq Khan Institute with an undergraduate degree in electronics engineering.

 

25. Vishal Shah
Chief Executive Officer, Screencastify

Vishal Shah is a seasoned entrepreneur and an influential supporter of startups, currently serving as the CEO of Screencastify, a leading platform in video communication and learning. With a proven track record in the ed-tech space, Shah founded LearnCore, a company specializing in training and coaching sales professionals, which he led to a successful exit. This experience underscores his ability to identify market needs, develop innovative solutions, and lead companies through periods of significant growth and strategic acquisition.

Shah has leveraged his insights and expertise to support numerous startup companies. He co-founded Catapult Chicago (Merged with 1871) to contribute to the broader tech ecosystem and fostering innovation across various industries. His strategic acumen and dedication to advancing technology for educational and professional development are evident in his leadership at Screencastify.

With over 500M videos created and 12M global users - Screencastify is making a global impact. Shah is driving the company's mission to be the premier platform for learning and communication globally. Under his guidance, Screencastify is enhancing the way educators, students, and professionals capture, create, and distribute video content, making learning and communication more accessible and impactful worldwide.