At CEO (Boardroom Media) we track over 1,000,000 startups and over 5,000,000 people who hold key positions in these companies. We use this directory of startups to highlight top employees, founders and board members we think deserve more appreciation than they are currently getting.
This list showcases the top Chicago based CEO’ operating in the Legal space. If you think a CEO’ is missing from this list, feel free to contact our editor on [email protected].
The individuals on this list have been included because of exceptional performance in one of the following categories:
- Innovation – Operating as a key part in an extremely innovative business or startup.
- Growth – Operating as a key figure in the growth and upscale of a market leading business or startup.
- Management – Showing exceptional management skills.
- Societal impact – Putting their business on the map for their positive societal or environmental impact.
Our Data – We source our data from OSINT (open source intelligence) and public directories such as Crunchbase, SemRush and many more. The data from these sources should be treated with a degree of caution and verified yourself.

Rakesh Madhava
Founder & CEO of Nextpoint
Rakesh Madhava is the Founder and Chief Executive Officer of NextPoint Inc., where he leads a unique team of computer scientists, litigation support professionals, and communication experts. He has 15 years of experience in legal technology and trial support with specific experience in white-collar criminal defense, breach of contract, intellectual property, shareholder suits, tortious interference suits, and product liability. Madhava is a frequent speaker on the topics of cloud computing and new technologies in electronic data management and is an avid participant in legal technology industry events. In 2005, he received a special proclamation for his work within the 7th Circuit Bar Association and is a member of the American Society of Trial Consultants, American Institute of Graphic Arts, and TiE, a network of professionals that fosters entrepreneurship.
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About Nextpoint: Nextpoint develops regulatory, compliance, and litigation software applications.

Jeffrey Eschbach
Founder & CEO of Page Vault
JEFFREY ESCHBACH is an entrepreneur and tech innovator, with over 20 years of experience creating new products and businesses. He is the founder and CEO of Page Vault Inc., a company that transforms Internet content into evidence for the legal world. Before that, Jeffrey built a career leading R&D initiatives at Intel Japan and Motorola Research Labs. After moving to Chicago a decade ago, he became immersed in its growing startup scene, and now advises and invests in early-stage companies there. He received an MBA with honors from The Kellogg School of Management, regularly teaches as a professor at the school, and serves as the Director of Program Outreach for the Kellogg Innovation and Entrepreneurship Initiative. He also holds undergraduate and Master’s degrees in Electrical Engineering from Purdue University. Jeffrey is a National Science Foundation Fellow, has earned 11 USPTO patents related to cloud-computing, and frequently speaks on startup and corporate innovation topics.
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About Chicago Early Growth Ventures (CEGV), Kellogg School of Management, Page Vault: Page Vault enables legal professionals to easily capture web content for use as evidence in the U.S. courts.
Wendell Jisa
Chief Executive Officer of Reveal
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About Reveal: Reveal is a global provider of eDiscovery, compliance and risk technology.
Martin Stasaitis
CEO of Devbridge
Martin is an original co-founder of Devbridge Group, and his focus today lies in leading the management team, executive hiring and strategic initiatives. He is responsible for accelerating growth and entrepreneurial vision within the organization.In addition to his work at Devbridge, Martin is a serial entrepreneur who is actively involved in the startup scene as a mentor and investor. He can be found advising startups as part of the StartupHighway accelerator, or defining strategy for young companies that incubated within Devbridge Group.Prior to co-founding Devbridge, Martin worked as a project and business manager at Monotype, Air Cycle Corporation and Sarpinos USA. Martin earned a Bachelor’s Degree in Finance from University of Illinois.
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About Devbridge: Devbridge is a Chicago-based software design and development company and strategic partner to B2B enterprises.

Dick Burke
Chief Executive Officer of Envoy Global
Dick Burke is the president and chief executive officer of VISANOW Inc. He is responsible for the development of the overall company strategy, marketing, sales, finance, business development and technology, while managing day-to-day operations. He has vast growth business and management experience as well as legal services insight. Prior to VISANOW, Burke served as president of Apartments.com, where he managed its business operations, including sales, marketing, product development, production, customer service and technology. During his tenure, the business attained record numbers in customers, traffic and revenues. Previously, Burke served as senior vice president of administration and corporate development for Classified Ventures LLC. In this capacity, he oversaw Homegain.com, the company’s online real estate business. In addition, he led the company’s corporate services division, comprised of corporate technology, legal, human resources, communications, facilities and corporate development. He played an integral role in successful acquisitions, including Apartment Home Living. Burke signed the papers that formed Classified Ventures LLC in 1997 and represented the company the same year in its acquisition of Visual Properties LLC, the predecessor of Apartments.com. Burke joined the organization in October 1998 as chief legal officer. Earlier in his career, he practiced law at Burke, Warren, MacKay & Serritella P.C. and Skadden, Arps, Slate, Meagher & Flom LLP. Burke received a bachelor’s degree from the College of the Holy Cross and a juris doctor degree from Georgetown University Law Center.
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About Envoy Global: Computer Software, SaaS
Gianna Scatchell
CEO and Co-Founder of Run the Call
Gianna Scatchell is the CEO and co-founder of Run the Call.
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About Run the Call: Run the Call is a real-time, location-based application that connects legal professionals to cover court appearances.
Jeremy Gottschalk
Founder and CEO of Marketplace Risk
Jeremy H Gottschalk is the founder and CEO of Marketplace Risk.
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About Marketplace Risk, Sittercity: The most comprehensive platform for risk management, trust & safety, compliance and legal strategy for marketplace startups

Jamal Jackson
CEO | Managing Attorney of Jackson Corporate Law Offices
Education: B.S. Business Administration – Creighton University Masters of Business Administration – Creighton University Juris Doctor – Creighton University. Practice Areas: Business Formation General Contracts Mergers & Acquisitions Franchising Intellectual Property Business Planning
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About Jackson Corporate Law Offices: Jackson Corporate Law Offices, a Chicago-based law firm, providing comprehensive legal services to entrepreneurial businesses of all sizes.

Wheeler Coleman
CEO and Executive Partner of EC-United
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About EC-United: EC-United is a boutique IT consulting firm specializing in providing innovative solutions to transform businesses.

Drew Stern
Founder & Co-CEO of Esquify
Drew Stern is an accomplished technology executive and entrepreneur with a portfolio of distinguished experience growing successful start-ups and creating, managing and growing strategic partnerships for Fortune 100 companies. Drew has held leadership, strategy and new product development roles at Salesforce, Buddy Media, American Express and Sprout Social. He has created and negotiated marquee partnership deals with the likes of Facebook, Twitter, Google and LinkedIn as well as led the international acquisition of Social.com (formerly BrighterOption). Drew’s business efforts have led directly to increased company valuation, new revenue and customer success. As a leader in the tech world, Drew’s broad-based background includes strategy, marketing, business development, general management, revenue growth and team building. Drew received his MBA in General Management, Strategy and Marketing from NYU Stern School of Business and his B.A., cum laude, from Tufts University.
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About Esquify: Esquify is a software company that provides AI automation workforce management solutions for legal review.
Robert M. Figliulo
CEO of SPR INc
Robert M. Figliulo is CEO at SPR INc.
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About SPR INc: SPR is a family of IT professional services firms in the Midwest that deliver high-value technology solutions.

Joe Stecher
CEO of TackleAI
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About TackleAI: TackleAI is an algorithms and neural network that automatically discover data on any type of document or image.