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Dale Jackson has over 10 years of work experience in various roles. From 2020 to present, they have been a Senior Account Executive at AgriWebb. From 2019 to 2020, they were a Farm Manager (Contract) at Toorloo Angora Stud. From 2011 to 2014, they were a Senior Recruitment Consultant at Ellington Savage Executive Search. From 2012 to 2014, they were the Owner (Coach) at Manly Surf Ski School. From 2009 to 2011, they were a Senior Recruitment Consultant at Ethos Corporation. From 2006 to 2009, they were a Branch Manager at Catalyst Human Asset Management Pty Ltd. Finally, from 2006 to 2006, they were a Consultant at Capital Commitments.

Dale Jackson completed their Matric at Diocesan College in 1998. Dale then attended the University of Cape Town from 2000-2003, where they earned a B.SocSc in Industry, Labour and Management. In 2005, they obtained a Postgraduate Diploma in Enterprise Management from the University of Cape Town.