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Jef Cracklen has a range of work experience in various roles and industries. Jef is currently working at Uptempo as the Senior Director of Education, overseeing product enablement and training. Prior to this, Jef worked at Allocadia in several roles, including Director of Education, Manager of Instructional Design and Facilitation, Lead Education Consultant, and Customer Success Manager. Jef also worked at Garaventa Lift as a Sales & Marketing Coordinator, at Mr Electric of Vancouver as an Operations Manager, at Disability Management Institute as an Early Intervention Program Coordinator, and at Angiotech as a Receptionist. Jef's early career included roles at Second Storey Theatre, Spectrum Job Search Centre, Pete's Tent and Awning, and the Academy of Learning.

Jef Cracklen has a Provincial Instructors Diploma in Education from Vancouver Community College (VCC), which was obtained from 2016 to 2017. Additionally, they attended the Academy of Learning from 2001 to 2002, where they studied Business Administration & Medical Office Assistant. Jef has also obtained various certifications from institutions such as LinkedIn and GP Strategies Corporation, specializing in areas such as strategic planning, change leadership, creative thinking, and public speaking.