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Lillie Chilen has had a varied career in software engineering and administrative roles. Lillie began their career in 2008 as a Communications Fellow at Oberlin College, followed by an Administrative Assistant role at Aquilo Partners, L.P. in 2009. In 2010, they worked as an Administrative Assistant at Loomis Group and in 2011, they were the Director of the Conservatory Challenge Initiative at Oberlin College. From 2013-2020, they worked at Omada Health, first as a Software Engineer, then as Engineering Team Lead, Engineering Manager of the Billing Team, and Engineering Manager of the Data Team. In 2020, they joined BackerKit as a Senior Software Engineer and is currently working at Dropbox DocSend as a Software Engineer since 2022.

Lillie Chilen attended Oberlin College from 2003 to 2008, earning a B.A. in Art History and a B.M. in Vocal Performance.