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Skyler Stearns has worked in a variety of roles since 2008. Skyler began their career as Floor Staff at Regal Entertainment Group. In 2013, they became a Mortgage Loan Originator at Stearns Lending, LLC. From 2013 to 2015, they worked as a Rental Property Portfolio Account Manager (Remote) at both Desert Sky Properties, LLC and El Dorado Residential Partners, LLC. In 2015, they also took on the role of Asset Manager (Remote) for M/Y Minderella. In 2016, they began working as an Investment Coordinator (Remote) for Veranda Senior Living, and as Human Resources for Trimavin / Triverify. In 2017, they began working as a Software Developer for Anivive, and as a Sales Intern for Gravitas Ventures.

Skyler Stearns has a Bachelor of Fine Arts (B.F.A.) from Chapman University, where they studied Creative Producing from 2012 to 2015. Prior to that, they attended Towson University from 2010 to 2012, studying Electronic Film and Media. Skyler obtained their High School Diploma from Sage Hill School from 2006 to 2010. Additionally, they obtained a Marketing Foundations certification from LinkedIn in November 2018.