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Caila Bolger has a diverse work experience in various customer success and management roles. Caila currently serves as the Principal Premium Customer Success Manager at LearnUpon since March 2021. Prior to that, they worked as a Product Manager at TransferMate Global Payments from May 2019 to March 2021. Caila also gained experience at Experian Data Quality, where they held positions including Senior Customer Success Manager and Customer Success Manager from July 2017 to April 2019. Additionally, they worked at Experian Data Quality UK in roles such as Customer Engagement Manager, Project Manager, and Senior Customer Operations Executive from May 2014 to July 2017. Caila's professional journey started as a Customer Support Coordinator at Experian Data Quality in July 2013. Caila also gained valuable experience as a Marketing and Event Planning Intern at The Women's Resource Center of Newport and Bristol Counties in 2012.

Caila Bolger has a Master of Business Administration (M.B.A.) degree from Salve Regina University, which they obtained between 2012 and 2013. Prior to that, they earned a Bachelor's degree in Marketing and Spanish from the same university, completing their studies between 2008 and 2012. Before attending Salve Regina University, Caila attended Notre Dame Academy School from 2004 to 2008. Additionally, Caila has obtained several certifications, including the PRINCE2® Foundation and PRINCE2® Practitioner certificates in Project Management from AXELOS Global Best Practice in September 2015. Caila has also achieved the Certified ScrumMaster® (CSM) certification, although the exact month and year are not provided.