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Christiana Gupta
CEO
Christiana brings years of leadership experience at Success Academy Charter Schools, where she served as a school leader at both the middle and high school levels, as well as a leader in the central offices. She has managed large cross-functional teams for technology, data, and strategic projects spanning the standardization of software selection, financial modeling, and developing an enterprise risk framework and KPIs. Working in Strategic Projects for the Office of the CEO, Christiana led the redesign of the network-wide parent communication strategy and the implementation of Zoom for 20,000 students and 3,000 staff for Success Academy’s remote instruction in the Fall of 2020.Prior to her work at Success Academy, Christiana completed the analyst program at Vista Equity Partners. During this time, Christiana worked with portfolio companies to develop and implement financial best practices and growth strategies.
Christiana holds a BS in Economics from The Wharton School of the University of Pennsylvania.
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Devon Caveney
DIRECTOR, DATA SERVICES
Prior to joining Simplicity Education, Devon worked at Success Academy Charter Schools in New York City, where she served as a College Access and Persistence Counselor, as well as an Associate to the High School Management Office. In these roles, Devon helped develop scalable processes for the high school, such as creating college advising support structures, optimizing student record management, and automating the transcript process. Devon was also an AmeriCorps fellow at Match Middle School in Jamaica Plain, MA, where she taught math and assisted the operations team.
Devon holds a master’s degree in Higher Education from Harvard Graduate School of Education, and a bachelor’s degree in Political Science from Williams College.
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Rebecca Gosla
ENGAGEMENT MANAGER
Rebecca joined Simplicity Education in 2022 as an Associate. Prior to starting at Simplicity, she worked for four years at Codman Academy Charter Public School in Boston. At Codman Academy, she served as the Data Manager and Student Recruitment Lead. Through her work, she doubled the number of recruitment events the school held, analyzed student achievement data, created dashboards to drive instructional and operational change, and spearheaded the school’s transition to a new gradebook. She has also served as Co-Chair of the Young Professionals Board for Friends of the Children-Boston.
Rebecca holds a master’s degree in Human Development and Psychology from Harvard Graduate School of Education and a bachelor’s degree in Cognitive Neuroscience from UC San Diego.