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Deepak Bassi has a diverse work experience spanning over several years. Deepak co-founded and served as the Vice-President of Client Experience at Karma Casting, where they specialized in creating unique brand experiences and managing talent recruitment and execution. Deepak also worked as a Member of the Board of Directors at St Joseph's Health System, supporting the care of the elderly in the community. As a Partner at Oakrock Group, Deepak focused on modern field and event marketing, combining creativity and technology. Deepak held various roles at iMD Health Canada, including Director of User Engagement/Acquisition and Director of Operations, where they played a key role in driving user adoption and managing relationships with healthcare associations. Prior to that, Deepak worked at BlackBerry as a National Account Director and National Client Manager, and at Microsoft as a National Field Manager and Field Manager.

Deepak Bassi obtained a BA degree in Sociology and Political Science from McMaster University, where they studied from 1998 to 2001. In addition, they pursued a Marketing Management postgraduate degree at Sheridan College from 1998 to 1999. Deepak also holds an Inbound Certification, which they obtained in July 2016 from HubSpot.