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Herb Holley started their work experience in 2005 at Dell as a Helpdesk Analyst, where they worked until 2007. Herb then joined Farmers Insurance in 2007 as a Helpdesk Analyst and remained in that role until 2018. In 2019, Herb joined Lone Star Circle of Care as a Network Engineer.

Herb Holley has a diverse education history. In 2010, they attended Austin Community College and obtained an Associate of Applied Science degree with a specialization in Local Area Network Systems - Security Administration. Herb graduated from Austin Community College in 2013. In 2019, Herb enrolled in Western Governors University and pursued a Bachelor of Science degree in Cloud and System Administration. Herb completed their studies at Western Governors University in 2020.

In addition to their academic accomplishments, Herb has obtained several certifications. In September 2018, they obtained the CompTIA A+ certification. In February 2020, Herb earned two more certifications from CompTIA: the CompTIA IT Operations Specialist – CIOS Stackable Certification and the CompTIA Network+ certification.