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Kiely Cross has extensive experience in the service industry, primarily as a bartender and bartender manager. Kiely started their career at Woody's Bar in 2018 as a food server before moving on to The Thornwood Bar and Beerhead Bar & Eatery as a bartender. In 2019, Kiely joined Granite City Food & Brewery as a food server and later transitioned to More Brewing Co. as a bartender. Kiely also worked as a bartender manager at BIGBY RESTAURANT MANAGEMENT, INC and Spotted Fox Ale House. In 2020, Kiely took on the role of Assistant Manager at DeskLabs. Kiely most recently worked as a bartender at The Club at Wynstone before joining MoLo Solutions as a Customer Operations Specialist in 2022.

Kiely Cross completed high school at Lake Park High School from 2008 to 2012, where they obtained a General Studies diploma. Kiely then went on to attend Harper College from 2018 to 2021, earning an Associate of Arts (AA) degree with a major in Psychology.

In addition to their formal education, Kiely has obtained several certifications. Kiely completed the "Cicerone" certification program in July 2018 and obtained the "OC Spray Handler/Course Completion" certification from the US Navy in July 2014. Kiely also has certifications in "Basset" from the Basset National Hospitality Training in May 2018 and "ServSafe Food Handler" from Food Handler Classes in May 2018. Kiely obtained the "Enlisted Aviation Warfare Specialist" certification from the US Navy in July 2014, as well as the "Expert Shooter M16 Rifle" and "Expert Shooter M9 Pistol" certifications, both from the US Navy in July 2013.

More recently, Kiely has obtained several certifications from LinkedIn. In June 2022, they obtained certifications in "All You Have to Do Is Ask: How to Ask for Help When You Need It," "Confidence-Building Strategies for Work and Life," "Improving Your Listening Skills," and "The Six Morning Habits of High Performers." In July 2022, they obtained certifications in "Communicating with Confidence," "Embracing Unexpected Change," "Learn Emotional Intelligence, the Key Determiner of Success," "Managing Your Emotions at Work," and "Preparing Yourself for Change." Additionally, they obtained the certification "Working with Upset Customers" from LinkedIn in July 2022.