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Erin A. Olsen's work experience begins in 1992 when they worked as a contract trainer for Silver Creek Computers. In 1994, they founded PCKeys Technology Solutions and served as the President/CEO. At PCKeys, Erin took on various roles such as instructor, instructional designer, sales manager, custodian, and hostess. PCKeys gained a reputation for providing customized training to enhance clients' technology knowledge and skills. In 2002, they became a contract subject-matter expert and on-screen talent for LearnKey Inc., where they authored and presented 20 computer-based training (CBT) courses. Starting in 2004, Erin joined The Training Associates, offering face-to-face and virtual training, instructional design, and video authoring/on-camera talent for clients in the U.S., Canada, and internationally. In 2008, they worked as a subject matter expert and on-camera talent at Career Academy until 2009. Erin also served as a subject matter expert and on-camera talent for Total Training from 2009 to 2012, creating learning pathways for Office 2010 and Windows 7 titles. From 2010 to 2014, they held the role of subject matter expert and on-camera talent at Skillsoft. Lastly, Erin worked at O'Reilly Media from 2012 as a subject matter expert, author, and on-camera talent, creating various video series on topics such as Windows, Excel, PowerPoint, Outlook, and SharePoint, among others.

Erin A. Olsen has a diverse educational background. Erin A. pursued a Bachelor's degree in Information Technology (B.I.T.) from American InterContinental University from 2006 to 2007. Following this, Erin earned a Master's degree in Instructional Design and Technology from the same university in 2007-2008.

Earlier in their education, Erin attended the University of Puget Sound from 1985 to 1988, where they focused on Politics with a minor in Asian Studies. Although they pursued a Bachelor of Arts (B.A.) degree, it is not specified whether they completed it.

In addition to their formal education, Erin holds certifications that complement their expertise. Erin A. became a Microsoft Certified Trainer (MCT) in June 2009 and also obtained the MCT: MCT Enrollment certification in April 2007 from Microsoft.