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 Career Planning 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.
Allison Robinson
CEO & Co-founder of The Mom Project
After having her son Asher in 2015, Allison identified how universally challenging it can be for American mothers to juggle the demands of motherhood with a full-time career and decided to tackle the issue on a national scale. Prior to founding The Mom Project, Allison spent 8 years at Procter and Gamble working on go to market strategies for leading household brands with a special focus on moms during her tenure on the Pampers brand. As CEO, Allison is responsible for delivering on the company’s mission of building a better workplace for women while supporting our customers through innovative talent solutions that help them attract and retain the diversity of backgrounds and perspectives they need to propel their businesses forward.
Follow Allison Robinson:
About The Mom Project: The Mom Project is a digital talent marketplace helping women remain active in the workforce.

Steve Fireng
Chief Executive Officer of Keypath Education
Steve Fireng is Global CEO at Keypath Education.
Follow Steve Fireng:
About Ad Venture Interactive Corp, Keypath Education, Nuro Retention: Keypath Education delivers programs that meet the needs of the future of work and help solve global, social, and economic challenges.
Amir Badr
Co-founder & CEO of Upkey
Follow Amir Badr:
About Upkey: Upkey is a provider of remote career readiness and talent engagement tools for students, universities, and companies.

Mitch Kirby
Co-Founder, CEO/CTO of TransparentCareer
Follow Mitch Kirby:
About TransparentCareer: TransparentCareer is building the next-generation career management platform for job seekers and employers.

Ryan Hoch
Co-founder and CEO of Overgrad
With a background in both technology and education, Ryan spends his time at Overgrad building relationships with universities and high schools around the country. Prior to his current role, Ryan was a high school math teacher in St. Louis with Teach For America and a technology consultant with Deloitte. Ryan is a graduate from the University of Illinois at Urbana-Champaign where he studied General Engineering. A die-hard Chicago Cubs fan, Ryan knows what it means to stay committed to a dream despite the circumstances.
Follow Ryan Hoch:
About Overgrad: Overgrad is an online platform that enables high school students to set long-term college and career goals.