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Derek Trickett has a diverse work experience spanning over two decades. Derek is currently working as a Software Architect at Buildium since 2018. Prior to that, they held various roles at HealthcareSource from 2010 to 2018, including Senior Director, Architecture & Platform Engineering, Director of Platform Engineering, Director of Architecture, Lead Architect, Software Engineering Manager, Principal Software Engineer, Senior Software Engineer, and Software Engineer. Before joining HealthcareSource, Derek worked as an Associate Business Systems Analyst at Oliver Wyman from 2006 to 2010, and as a Web Developer at CoreWeb from 2004 to 2006. Derek started their career as a Business Analyst/Developer at First Notice Systems in 1998 and also worked as a Data Entry Specialist there.

Derek Trickett attended Malden High School from 1997 to 2000, where they pursued a general high school education. In 2000, they briefly attended Wentworth Institute of Technology, focusing on Computer Science. Following that, in 2002 and 2003, Derek pursued a Certificate in Microsoft .NET/Oracle Solutions at Boston University, specializing in Computer Science.