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Bailey Robertson has a diverse work experience spanning multiple companies and roles. They began their career in 2015 at Entrata, where they worked as a Leasing Professional, Senior Team Lead, Performance Coach, and Quality Manager. In 2018, Bailey moved on to Weave HQ, where they held positions as a Customer Onboarding Specialist, Department Trainer (Customer Onboarding), and Learning Experience Designer. In 2022, Bailey joined The Elements Financial Planning System™ as the Head of Customer Success before transitioning to their current role as a Product Enablement Manager at Webflow.

Bailey Robertson attended Brigham Young University from 2011 to 2017, where they obtained a Bachelor of Arts degree in American History/Legal Studies. Additionally, Bailey obtained certifications in "Become an L&D Professional" and "Elearning Tips" from LinkedIn in December 2020.