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Rory McKenna's work experience includes various roles in different companies. Rory started in 1995 as an intern in the Cellular Subscriber Division at Motorola. After that, Rory interned at Caltech in 1997 as a web developer. In 1998, Rory was an intern at Idealab. From 1999 to 2001, Rory worked as a lead developer at PayMyBills.com. In 2001, Rory worked as a developer at GoTo.com and also worked as a contractor. From 2004 to 2006, Rory served as a senior/lead developer at Overture, a Yahoo! company. In 2007, Rory joined Yahoo! Inc as Director of Engineering and remained in that role until 2015. Lastly, Rory worked as the CTO at Smiletime from 2015 onwards.

Rory McKenna attended Caltech from 1995 to 1999, where they obtained a Bachelor of Science degree in a multidisciplinary field encompassing Electrical Engineering, Computer Science, and Applied Physics.