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Randy Pensinger worked as a Software Engineer at MediaAlpha, Inc. starting in 2016. Prior to that, they worked at Porch.com from 2013 to 2015, where they focused on core backend development, continuous integration, data aggregation, denormalization, and migration integrity. From 2011 to 2013, Randy was a Senior Software Engineer at Opera Solutions. Before that, they worked briefly as a Software Engineer at Gaikai in 2011. Randy's earliest work experience was at SpeedTax, where they worked as a Software Engineer from 2009 to 2011.

Randy Pensinger's education history includes a four-year period from 2005 to 2009 at Stanford University. During this time, they pursued a Bachelor of Science (BS) degree in Computer Science.