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Randall Oshita has a variety of work experience in the field of IT. Randall began their career as a Systems Administrator at Uniserve, Inc. in 2000 and worked there until 2003. From 2003 to 2006, they held the role of Systems Administrator at Hawaii Pacific University and then Pacific Wireless Communications Pty Ltd. In 2006, they joined Evolution Financial Group as a Systems Administrator, where they remained until 2019. In 2019, Oshita became a Systems Administrator at Pacific City Bank until 2021. After that, they served as VP of Information Technology at Griffin Capital Essential Asset REIT, Inc. from 2021 to 2022. Randall then worked as an Infrastructure Engineer at Velocity Mortgage Capital from 2022 to 2023. Currently, Oshita is the VP and IT Manager at Whittier Trust Company.

Randall Oshita holds a Bachelor's degree in Business Administration with a focus on Computer Information Systems from Hawaii Pacific University. In addition, they have obtained several certifications including Palo Alto Networks Certified Network Security Administrator, VCP-DCV 2020 from VMware, Microsoft Certified Solutions Expert for Productivity (Exchange Server 2016) from Microsoft, CCNA from Cisco, CompTIA Network+, CompTIA Security+, Microsoft Azure Fundamentals, Microsoft Certified Solutions Associate for Windows Server 2016, and Microsoft Certified Solutions Expert for Core Infrastructure.