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Cullen Costello has a diverse work experience starting in 2015. Cullen owned and operated Easy Math Tutoring from January 2015 to December 2017. In 2015, they also worked as an Area Manager at Vantage Marketing until December 2016 when they were promoted to Sales Manager, a position they held until December 2017. In 2018, they joined Tuple as an Account Executive until July 2019. From July 2019 to May 2020, Cullen worked as an Account Executive at Samsara. Cullen was then promoted to Account Executive Team Lead at Samsara from May 2020 to January 2022. From January 2022 to January 2023, they served as a Senior Account Executive in the Mid Market team at Samsara. Currently, they hold the role of Team Lead, Senior Account Executive for the Mid Market team at Samsara where they designed a training and development program for new representatives and conducted in-person training for over 60 representatives. This training cohort saw significant improvements in average pipeline generation and free trials shipped.

Cullen Costello has a Bachelor of Science degree in Finance from Arizona State University. They also obtained an International Business Certificate from Universitat Autònoma de Barcelona. Additionally, Cullen has certifications in Coaching Skills and Feedback Skills from LifeLabs Learning, obtained through Samsara.