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Chesney Jennings has worked in a variety of roles since 2005. Chesney began their career as an Electrical Engineer at Martin Rees Electrical in 2005. In 2009, they became a Sole Trader at Jennings Electrical. From 2010 to 2012, they worked as a Machine Technician at RECORD INDUSTRIAL BRUSHES LIMITED. In 2012, they became a Web Developer at Pach Web Solutions, where they interacted with clients and worked with WooCommerce and Wordpress. From 2017 to 2021, they worked as a Technical Support & Web Developer at Recruitment Entrepreneur, a UK-based investor in early to mid-size recruitment start-ups. Chesney also worked as a Senior Developer at Studio Sixty London from 2017 to 2021. From 2021 to 2022, they worked as a Wordpress Developer at Complex Creative, a Website Developer at Fresh Pies, and a Website Developer at TwentyOne12 Media. Chesney is currently the Head of Web Development at ExSeed Health.

Chesney Jennings attended Coleg Sir Gar from 2005 to 2008, where they earned a C&G 2330 in Electrical and Electronics Engineering. Prior to this, they attended Ysgol gyfun Pantycelyn from 2000 to 2005.