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Dennis Espen has a diverse work experience, starting in 2013 when they worked as a Staff Accountant at Coin Master. In this role, they assisted clients in automating their financial compliance environment and implementing new strategies to improve productivity. Dennis then moved on to work as an Accountant at Chief Executive Group, where they managed accounts and maintained relationships with clients. In 2013, they also took on the position of Director Client Management at Management Solutions International (MSI), where they were responsible for managing and supporting client requests and ensuring quality assurance. Most recently, in 2019, they became an Assistant Director at Trusts and Private Family Foundations, where they focused on providing support and lifesaving resources to members of the armed forces and their families.

Dennis Espen completed their Bachelor's degree in Accounting and Business/Management from the University of Johannesburg, studying from 1996 to 2000. Additionally, they pursued a Bachelor of Business Administration - BBA degree in Accounting and Finance from the University of Cambridge. The specific years of their studies at the University of Cambridge are unspecified.