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Sherwin H. has over 20 years of work experience. Sherwin began their career in 2000 as a National Hostess Manager at SA Roadlink. In 2007, they became a Network/Sales Team Lead at Universal Healthcare (Pty) Ltd. In 2011, they were appointed Sales Team Manager at CONNECTAQUOTE. From 2012 to 2014, they served as a Customer Service Team Manager at Webhelp. In 2014, they became a Senior Tour Operator at Imagine Cruising SA. In 2019, Sherwin H. was hired as a Business Development Manager at ChatMarshal Live Chat. In 2021, they were appointed International Business Development at HelpSquad. Currently, they are an International Certified Channel Manager at LiveHelpNow.

Sherwin H. received a Certificate in Computer Systems Networking and Telecommunications from Chanimal University and a Certificate in Human Resources Management and Services from Damelin in 2012-2013.