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Shaylee Kennedy has a diverse work experience spanning different industries and positions. Shaylee began their career as a Senior Banking Consultant at Westpac New Zealand Limited in 2010 before moving on to become a Home Finance Manager and later a Westpac Premium Relationship Manager at Westpac. In 2015, they joined SAI Global Property as a Business Development Manager, where they stayed until 2018. Shaylee then worked at triSearch as a Business Development Manager until 2020. Shaylee then transitioned to Ms Mindset Boss, where they served as a Sales Coach until the end of 2022. Currently, they are working as the Head of Customer Operations at Scorebuddy.

Shaylee Kennedy attended Kaplan Professional from 2013 to 2015 to pursue an Advanced Diploma in Financial Planning, specializing in Financial Planning and Services. In addition, they obtained a Diploma in Financial Planning from Kaplan in July 2014.