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Chilombo Olawoye has a diverse work experience spanning various roles and industries. Chilombo is currently the Chief Operations Officer and Vice Chair at OBSIDI, a position they have held since September 2023 and January 2023 respectively. Prior to that, they were the Chief Operating Officer at OBSIDI from December 2020 to May 2023. Before joining OBSIDI, Chilombo served as the Executive Director at The Teresa Group from March 2020 to December 2020. Chilombo also worked as a Duty Officer at the City of Toronto from December 2018 to March 2020, and as a Program Manager at The Teresa Group from February 2016 to December 2018. Chilombo's previous experience includes working as a Manager at YWCA Toronto from March 2015 to March 2016, and as a Community Outreach Worker at Youthlink from October 2009 to April 2011.

Chilombo Olawoye has a Master's degree in Social Work from the University of Toronto, which was obtained from 2017 to 2019. They also have a Postgraduate Certificate in Non-Profit Management and Leadership from Seneca Polytechnic, completed between 2014 and 2015. Additionally, Chilombo Olawoye holds a Bachelor's degree in Sociology from the University of Toronto, although the specific years of completion are not provided.