ABOUT US
Meet the people behind the data.
FOUNDER + CEO
Christiana founded Simplicity in 2020 to help school leaders make better decisions with data they can actually use. After seeing how fragmented systems and manual reporting slowed down schools during her time as a leader at Success Academies, she built Simplicity to give leaders and boards a clearer view of school health, earlier insight into risks, and the confidence to act.
Christiana Gupta
CTO
Jason leads Simplicity’s technology strategy, bringing deep experience building platforms that turn fragmented school data into clear, actionable insight. He previously served as CTO at Panorama Education and CPO at Everyday Speech, where he led data, engineering, and product teams developing tools used by millions of students and educators.
Jason Larsen
DIRECTOR, DATA SERVICES
Devon leads our Data Services team to help schools transform complex data into reliable systems, clear reporting, and practical insight. Before joining Simplicity, she worked at Success Academy Charter Schools in New York City as a College Access and Persistence Counselor and Associate to the High School Management Office. She also served as an AmeriCorps fellow at Match Middle School in Jamaica Plain, MA, where she taught math and supported school operations.
Devon Caveney
ENGAGEMENT MANAGER
Rebecca partners with school teams to make data systems easier to use, easier to trust, and easier to act on. She joined Simplicity in 2022 after four years at Codman Academy Charter Public School in Boston, where she served as Data Manager and Student Recruitment Lead. Her work bridges school operations, data management, and client support.
Rebecca Gosla
ASSOCIATE
Kate brings experience across education, public health, and nonprofit technology. Before joining Simplicity, she managed projects for NTEN’s national nonprofit technology conference, where she improved internal workflows and built dashboards that increased data visibility across teams. At Simplicity, she supports client work with a focus on clear systems, strong execution, and actionable reporting.