His father, Paul Woodland, was an economist, and his mother, Fay, worked as a teacher.
[3] Woodland attended Bond University but did not complete his bachelor of Law.
[3] During a training exercise Woodland injured himself and later transferred to the Australian Psychology Corps where he helped soldiers returning from war.
[5] In 2010, Woodland retired from the Australian Army to help his mother in her childcare business.
[4] In January 2016, Woodland and his mother sold their three childcare businesses and Woodland then went on to found Xplor Technologies,[3] a software platform that removes administration from parents, educators and centres so they can focus on teaching and learning from Venture Capital Firm[7] and grew to become the second largest childcare platform in Australia.