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Laila McCaffrey has had a varied work experience since 2015. Laila began their career as a Shift Lead Barista at Pekoe Sip House. In 2015, they also began working with SheJumps as a SheJumpsCU. In 2017, they began working at the University of Colorado Boulder as a Peer Business Writing Consultant, Microsoft Excel Learning Assistant, and Wardenburg Student Health Board. In 2018, they worked as a Website Project Manager for ELEVENPINE, as well as a Sales, Sponsorship, and Programs Intern for BOLDERBoulder 10K. In 2019, they began working at Flowhub as a Junior Product Manager, Senior Implementation Project Manager, Implementation Project Manager, and Junior Implementation Project Manager.

Laila McCaffrey began their educational journey at Niwot High School, where they were an International Baccalaureate (IB) Diploma Recipient. Laila then went on to study abroad at Trinity College Dublin in 2016, where they earned a degree in English. In 2017, they completed an apprenticeship on Regenerative Global Business Projects in Bahía de Caráquez, Ecuador. Finally, Laila earned a Bachelor's degree in Business Administration: Operations Management and Leadership from the University of Colorado Boulder in 2019.