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Sina Shekou has held a variety of roles since 1996. Sina began their career at Oracle Corporation, where they served as an Operations Manager for Western Support Service and a Salesperson for Support Services. Sina then moved to Salesforce.com, where they held the positions of Director of Interactive Marketing and Business Development. In 2002, they co-founded Propertyware, Inc. and served as its CEO. In 2009, Shekou became the President of LeaseStar, Propertyware, and LeaseStar Marketing Solutions and SMB Division at RealPage, Inc. In 2015, they founded PlanChat, Inc. and served as its CEO, as well as becoming a Board Advisor at FRONTSTEPS. Finally, in 2017, they became the CEO of Aptly.

Sina Shekou obtained a BA in Marketing and a BS in Biology from the University of Colorado Boulder between 1992 and 1996. In 2001 and 2002, Shekou completed a Dive Master certification from PADI in the field of Scuba Diving.