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Anna Kalandyk has a diverse work experience history. Anna started their career as an Intern at the Center for Access and Attainment (CAA) Research Lab in 2014, where they built research skills and aided in creating a tutoring program. Anna then worked as a Seasonal Driver Helper at UPS in 2016, where they assisted the driver with moving packages and organizing the truck. In 2016, Anna also served as an Honors Mentor in the DePaul Honors Program, welcoming and supporting incoming students.

In 2017, Anna joined DePaul University, initially working as a Circulation Assistant in the library, providing assistance to patrons and managing library resources. Anna also worked as a Student Research Assistant, collaborating with a professor on a research project that focused on representations of urban space and architecture in video games. Anna's role included providing animated visualizations and researching graphics used in everyday life.

In 2018, Anna joined NetherRealm Studios (WB Games) as a Quality Assurance contract tester. Their responsibilities included testing new builds of mobile and console games, reporting bugs, and staying updated on game updates.

In 2019, Anna joined Jackbox Games briefly as a Quality Assurance professional before transitioning to High Voltage Software. At High Voltage Software, they had progressively advanced roles, starting as a Quality Assurance Analyst and later promoted to Lead Quality Assurance Analyst. Currently, Anna serves as the Quality Assurance Manager at High Voltage Software.

Anna Kalandyk attended DePaul University from 2014 to 2018, where they earned a Bachelor's Degree in Game and Interactive Media Design.