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 Employee Benefits 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.
Jasmine Shells
CEO & Co-Founder of Five to Nine
Jasmine Shells is the CEO and Co-Founder of Five to Nine. Jasmine moved to Chicago after college and noticed meeting new people and finding the go-to spots in the city was hard. She found this was the same situation for most transplants and led her to create a social community for millennial professionals embarking on a new journey. Five to Nine believes in building a strong community over shared experiences. The company currently has over 2000 members and is continuing to grow with their action-packed member socials and events. Jasmine and her company have been featured in TED, Chicago Inno, the Chicago Tribune, Technori and Bootstrapping in America. Jasmine is a proud graduate of the University of Notre Dame and loves to dance salsa and previously lived in Spain. In addition to her passion for connecting people, she loves to inspire others to create their own opportunities and take the leap.
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About Five to Nine: Five to Nine manages & evaluates virtual event programming so you can focus on building the employee experience.
Joseph Holberg
Founder & CEO of Spring
Joe is the Founder & CEO of Spring, the #1 rated financial wellness benefit in the US. He coined the term “financial justice” and gave a TEDxTalk to that end: https://www.youtube.com/watch?v=azk_ObDWkqk Additionally, he is the author of both “Rogue Finances: The “Un-system” Designed to Help You Become Financially Healthy, Successful, and Awesome” and most recently, “A Brief Discourse on the Definition and Tenets of Financial Justice” He understands the financial challenges and opportunities Americans face each day and he is building a new kind of financial company that strives to be the polar opposite of the entrenched status quo. His perspective is drawn from a variety of experiences including working at Google, teaching middle school math on the West Side of Chicago, and having created a loan underwriting system for the he Capital Good Fund, one of the country’s largest microfinance organizations. He is an avid coffee drinker, a reader, a bibliophile and an angel investor.
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About Inverted Ventures, Spring, The Economic Club of Chicago: Spring provides a holistic, unbiased financial wellness benefit to companies to increase employee recruitment, productivity, and retention.
Rochelle Gorey
Co-Founder & CEO of SpringFour
Under Rochelle’s leadership, SpringFour became a Certified B Corporation, of which only 2,200 such organizations exist worldwide, won the 2015 Promontory Financial Group’s Empowerment Award for Financial Innovation, was a finalist for Google for Entrepreneur’s program for Women Founders and was selected for the WiSTEM program at 1871, Chicago’s Center for Technology and Entrepreneurship and was chosen as the Top Venture for the Points of Light Civic Accelerator Spring 2017 program. SpringFour was one of six fintech companies chosen for the BMO Harris/1871 Fintech Partnership Program and in 2017 was a finalist for the BAI Global Innovation Award for its work with U.S. Bank, Chicago’s Fifty on Fire Award and the Midwest Women in Tech’s Fintech Award. In 2018, SpringFour was named by FinXTEch/Bank Director as a finalist for the Most Innovative Solution of the Year for its work with U.S. Bank. Ms. Gorey has more than 20 years of experience in public policy, government relations, homeownership and asset building fields through her consulting and employment. She has a bachelor’s degree from James Madison College of Michigan State University and a Masters in Urban Planning and Policy from the University of Illinois at Chicago.
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About SpringFour: SpringFour’s technology platform connects consumers to local financial health resources, tools and products. SpringFour is a B2B solution.

Claire Lew
CEO of Know Your Team
Claire Lew is the CEO of Know Your Company, a software tool that helps business owners overcome company growing pains. Her company, Know Your Company, has helped over 15,000 people in 25 countries at companies like Airbnb and Kickstarter. Claire’s mission in life is to help people become happier at work. She speaks internationally on how to create more open, honest workplace environments, and has been published in Harvard Business Review, Fortune, Inc, Forbes, among others.
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About Know Your Team: Know Your Team is software that helps managers become a better leader.

Eric Rentsch
CEO & Founder of Code SixFour
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About Code SixFour, Zywave: The Code SixFour Benefits Consulting Cloud empowers insurance agents and benefits brokers to deliver better benefits outcomes to employers.

David Aronson
CEO of Peanut Butter
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About Peanut Butter: Student loan assistance as an employee benefit