Anna Croft

Senior Benefits Specialist at Chicago Cubs

Anna Croft is a seasoned professional specializing in benefits administration, currently serving as a Senior Benefits Specialist for the Chicago Cubs since July 2025. Previously, Anna held various roles at Wintrust Financial Corporation from May 2019 to July 2025, including Senior Benefits Analyst and HR Data Center Team Lead, showcasing a strong background in HR and benefits management. Prior to that, Anna gained experience as a Relationship Banker at MB Financial Bank and served as a Nanny and Swim Instructor, developing essential skills in communication, management, and teamwork. Anna holds a Bachelor's degree in General Studies with an Emphasis in Health Sciences from Illinois State University, completed in 2017.

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