EssayJack is an interactive web platform with a patented solution that pre-structures student essays, reduces writing anxiety, and allows educator customisation and feedback. EssayJack has been ranked as one of the top teaching digital innovations in the world by the British Council and Cambridge English and was created by award-winning educators and can be customised for almost any writing task. EssayJack is now being adopted by various organisations, and was 2017 Finalist for Best Higher Education Solution at the 2017 Tech Edvocate Awards amongst other recognitions and awards it was and is considered for. We speak to the two co-founders about how this idea was born and the challenges in bridging technology and education.