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Oscar Webb has a wealth of experience in customer success and sales. Oscar began their career in 2011 as a Contract Sales Executive for Gradwell. In the same year, they also worked pro bono for Deutsch Palliativ Stiftung as a Photographer, Digital Designer, and Copywriter. In 2012, they worked as an English Survey Interviewer for Trendtest GmbH and as an Account Manager and Senior Account Manager for Vocus. From 2014-2019, they worked as a Full-Time Parent and Tripeasel Guest Blogger and Travel Expert and from 2016-2019 as a Global Customer Success Lead and Customer Success Manager for BridgeU. In 2019, they founded Oscar Webb Consulting, working as a Customer Success Consultant. In 2020, they worked as an Interim Head of Customer Success for Passion.io. Oscar currently works as a Senior Customer Success Strategy Consultant for Planhat.

Oscar Webb attended Monmouth Comprehensive School before continuing their education at Bath Spa University, where they earned a BA Hons in Creative Arts in 2008.