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Jackie Szramowski has had diverse work experience in various companies and roles. Jackie started their career as a Media Relations Specialist at Children's Hospital of Pittsburgh in 2006, where they handled media requests and wrote press releases. In 2007, they became a Technical Recruiter at Oxford Global Resources, identifying local IT talent in Pittsburgh. In 2010, they joined American Partners Inc. as a BI Delivery Manager, specializing in connecting top talent with opportunities. From 2011 to 2022, they worked at Penske Automotive Group, starting as a Human Resources Specialist and progressing to roles such as East Region Recruiter, Manager of Talent Acquisition, and eventually Director of Talent Acquisition. Penske Automotive Group is a Fortune 500 company and is ranked among the World's Most Admired Companies.

Jackie Szramowski attended C.B. West from 1998 to 2001. Jackie then pursued a degree in English Writing at the University of Pittsburgh from 2001 to 2006.