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Shashi Singh has a diverse work experience spanning over several companies and roles. In 2011, Shashi began working as a Jr. Software Developer at AnyLinuxWork Pvt. Ltd. until 2013. From 2011 to 2019, Shashi also worked as a Freelancer Software & Web Developer, specializing in Ruby on Rails development. In 2014, Shashi worked as a Software Developer at TipHive until 2015. In the same year, Shashi also worked as a Ruby on Rails Developer at Shirtly. In 2017, Shashi joined Virtualspirit as a Ruby on Rails Developer, and stayed until 2019. More recently, Shashi joined CareerBuilder in 2019 as a Senior Software Engineer and was later promoted to Engineering Lead in 2022.

Shashi Singh completed a Master of Computer Applications (MCA) degree in Computer Software Engineering from Rajiv Gandhi Prodyogiki Vishwavidyalaya from 2008 to 2011. In 2020 to 2021, they pursued a course in Design Thinking & UX/UI from The Interaction Design Foundation. Additionally, in June 2021, Shashi Singh obtained a certification in Data-Driven Design: Quantitative Research for UX from The Interaction Design Foundation.