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Jason Stockwood

CEO, Simply Business

Jason is responsible for developing Simply Business and challenging the traditional world of insurance through technology and data science.

He joined Simply Business from the global dating website,, where he was International Managing Director. Prior to this, he spent time working in the travel industry as managing director at Travelocity Business, and in commercial roles at Trailfinders, and He has also held board positions with Skyscanner and The Drinkaware Trust. Simply Business was voted ‘The Best Company to Work For’ in The Sunday Times in both 2015 and 2016. Jason was also voted CEO of the Year in 2016 by the same publication, the first award he has received since his 20 metre swimming badge in 1981. In 2017 Simply Business was awarded its B-Corp accreditation.