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Zachary Obasiolu has worked in the tech industry since 2014. In that year, they began working as a Genius at Apple, where they were in charge of handling any issues customers had with their devices or software. In 2015, they became the Director of Digital Design/Marketing at PaidEasy, a mobile payments application. In 2016, they were the Project Lead at Obasiolu Dev, where they and their team built custom websites, web apps, e-commerce stores, and iOS apps. In 2017, they became a Co-Founder/Board Member at Chow, a cannabis marketplace that focuses on automated compliance for cannabis brands. Most recently, in 2021, they became the Co-Founder/CEO of maskedMED, a platform designed to empower Medical Professionals with tools to help them grow and earn additional income.

Zachary Obasiolu attended the University of Massachusetts Dartmouth from 2012 to 2013. Zachary also attended Boston Trinity Academy.