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Simon Wheeldon has a diverse work experience, starting with their role as an Adjudicator at The Financial Ombudsman Service from July 2013 to March 2015. Simon then co-founded Pluhoo in March 2014 and held the position of Co-Founder until March 2016. Simon went on to work at BitPoster as an HR Manager from March 2015 to August 2015, where they handled various responsibilities including recruitment, office management, and representing the company at events. Simon also worked as an Operations Manager at BitPoster from August 2015 to June 2016, where they dealt with customer service, client liaison, social media management, and day-to-day operations.

In 2015, Simon co-founded Send a Box and served as a Co-Founder until April 2019. Simon then joined Brandable & Co. as the Head of Solutions & Development from November 2020 to July 2022. Simon was a Co-Founder at Communal Brew from January 2021 to November 2022, where they established a free slack community and upcoming micro podcast series for founders and freelancers. Simon also co-founded Hive52 in July 2021 and served as a Co-Founder until April 2023.

Additionally, Simon worked as an Advisor at Mallconomy from March 2022 to June 2023, and as a Director & Shareholder at JamPot since March 2016 and Investor at Private Investments since May 2023. At JamPot, they initially held the role of Co-Founder & Head of Ops, where they provided remote business support in various areas such as admin, operations, HR, and marketing.

Overall, Simon Wheeldon has gained extensive experience in various roles, particularly in co-founding and managing multiple businesses, as well as providing support and advisory services.

Simon Wheeldon began their education at King Edward VI Grammar School in Louth, Lincolnshire, where they attended from 2003 to 2010. Simon then went on to earn a Bachelor of Arts (B.A.) Honors degree in Landscape Architecture from The University of Sheffield, from 2007 to 2010. In 2016, Simon completed a Full Stack Developer Course at Thinkful, specializing in Web Development. Additionally, they have obtained several certifications including FA Youth Module Level 1 from The FA in April 2013, FA Level 2 Coaching Badge from The FA in March 2013, Fire Marshall certification from St Johns Ambulance in March 2012, FA Level 1 Coaching Badge from The Lancashire FA in October 2010, Duke of Edinburgh Gold Award from the Duke of Edinburgh Award Scheme in February 2008, Duke of Edinburgh Silver Award in January 2007, and Duke of Edinburgh Bronze Award in January 2006.