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Kesa Iskra has a diverse work experience spanning various roles and industries. Kesa started their career in 2007 as a Private Dining & Events Manager at De La Costa Restaurant. In 2008, they worked as an Event Coordinator at On The Scene, and also took on independent contractor roles for various Destination Management Companies and National Meetings Companies. Kesa then became the Owner/Partner of Connect Chicago in 2008, where they focused on establishing brand identity and credibility in the retail marketplace and Outdoor Apparel industry. In 2011, they transitioned to Kuoni Destination Management USA, initially working as an Account Manager before being promoted to National Account Executive. From 2019 to 2021, Kesa worked at MC&A, first as the Director of Creative Services and then as the Vice President of Creative Services.

Kesa Iskra attended St. George's School from 2000 to 2003, during which, the degree or field of study they pursued is unknown. Kesa then continued their education at The School of The Art Institute of Chicago from 2003 to 2007, specializing in Fashion Design and Art Administration.