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Lester San Jose has a diverse work experience. Lester started their career in 2007 at Hyperkin, where they performed various tasks including data entry, customer service, and warehouse support. Lester then worked as a Glendale Martial Arts Examiner at Examiner.com in 2010, providing information and commentary on martial arts. In 2011, Lester briefly owned their own business, illGottenGames. From 2012 to 2018, they worked at Convergys, primarily providing inbound sales and technical support. Lester joined Out of the Box Technology in 2018, initially as a ProAdvisor Services Account Manager Tier I, and later as a Business Development Specialist, where they focused on SEO optimization, utilizing HubSpot for campaigns, and designing IT solutions. In 2020, they briefly worked at Adecco as a Contact Center Agent before returning to Out of the Box Technology as a Data Specialist.

Lester San Jose attended San Diego City College from 2001 to 2003, where they earned an Associate of Arts (A.A.) degree in English Language and Literature, General. Lester then went on to pursue further education at California State University, Los Angeles, from 2004 to 2006. During this time, they obtained a Bachelor of Arts (B.A.) degree in English.