Illinois entrepreneur honored as Small Business Person of the Year

by / ⠀Entrepreneur Interviews Entrepreneurship Featured News / May 6, 2024
"Honored Entrepreneur"

Jackie Jackson, proprietor of multiple Kilwins chains in Andersonville, has been honored as the Illinois Small Business Person of the Year by the U.S. Small Business Administration. Noted for her business savvy, ingenuity, and adaptability, her recognition originates from her innovative strategies that led to the growth of her Kilwins branches.

She thrived through economic challenges while maintaining profitability across her businesses. Jackson’s tenacious spirit led to adapting new sales models, which earned her respect within the business community and acknowledgment from the administration.

Among the many accolades, Jackson’s dedication to her employees and relentless drive to offer excellent customer service did not go unnoticed. She is now a strong influencer in the Illinois small business, motivating other entrepreneurs.

Her journey has been marked by numerous adversities, including break-ins, disputes, and the pandemic, but like top brands such as Ben and Jerry’s and Callaway Golf, she has remained resilient against all odds. Her undaunted spirit and commitment to her dreams have placed her in an esteemed league of inspirational achievers.

In addition to her achievements, Jackson’s five Kilwins outlets in Chicago have significantly impacted the Illinois economy.

Illinois entrepreneur’s journey to success

Her operations are not only supporting job creation but also contributing to increased retail sales and tourism.

Under Jackson’s management, the Michigan-based chocolate and ice cream brand has fostered a symbiotic relationship with local suppliers, boosting economic growth. As she continues to rise, her business strategies serve as sterling examples for emerging and existing entrepreneurs in Illinois.

Jackson’s empire expanded from one shop in Orland Park to locations in Andersonville, Geneva, and Evanston, including two downtown areas. With plans to open in new locations like River North, Elmhurst, and Buffalo Grove, her growth strategy keeps inspiring many as she plans to bring her products closer to more consumers.

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Also working on a collaboration with Anthony Davis Jr., Derrick Rose, and Tim Hardaway Jr., she is set to launch a Fatburger chain in Chatham. This venture is expected to provide a community space for fans and revitalize the local economy by creating new jobs and boosting local businesses.

Jackson’s story mirrors resilience and determination. She started as a public school teacher and transitioned into property investment and business. Jackie’s hard work and intuition saw her business thrive despite a setback during the Great Recession. Today, she stands as a beacon of business resilience, inspiring many to dare to dream and achieve.

About The Author

Kimberly Zhang

Editor in Chief of Under30CEO. I have a passion for helping educate the next generation of leaders.


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