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Jacob Winkler has a diverse work experience, beginning in 2015. Jacob started as a ITS Helpdesk Employee at Centre College, and also worked as a 03' Boy's Head Soccer Coach at Central Kentucky Soccer Club. In 2016, they worked as a Summer Intern at Saint-Gobain, where they built a staffing plan database in Microsoft Access and worked on various other technical jobs. Jacob also worked as a ITS Helpdesk Employee at Centre College ITS and a 02' Boy's Head Coach at Central Kentucky Storm Soccer Club. In 2017, they began working as a Software Engineer at AVAIL (getavail.com). Most recently, in 2020, they began working as a Backend Software Engineer at Sonar.

Jacob Winkler attended Centre College from 2013 to 2017, where they earned a Bachelor's degree in Computer Science with a minor in Psychology.