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Pip Shirley has a diverse work experience, starting in 2000 as an Executive Support Officer at Clarence City Council. From 2002 to 2004, they served as the Executive Officer to the Director of Community Corrections at the Department of Justice, focusing on strategic planning, statistical analysis, and policy development. In 2004, they joined the Magistrates Court of Tasmania as a Senior Project Officer. From 2005 to 2008, they worked at the Department of Justice, managing various projects related to parole board administration and court-mandated diversion of drug offenders. Pip then joined the Department of Health and Human Services in 2008, where they served as an Executive Officer, responsible for projects such as the review of the Youth Justice Act and the development of a system for reviewing child deaths in Tasmania. In 2013, Pip joined the Tasmanian Law Reform Institute as a Senior Research Officer, focusing on the development of an issues paper and consultation with key stakeholders. Pip returned to the Department of Health and Human Services in 2013 as a Senior Analyst, and later joined the Department of Premier and Cabinet (Tas) in 2014. At the Department of Premier and Cabinet, they held various roles, including Senior Policy Analyst, Acting Assistant Director, Acting Manager of Government and Legal Services, and currently serves as the Assistant Director of Strategic Policy and Projects.

Pip Shirley's education history includes several degrees and diplomas from the University of Tasmania. In 1996 and 1997, Pip obtained a Graduate Certificate in Management, with a focus on Business Administration and Management. This was followed by a Graduate Diploma in Business Administration from 1998 to 1999. In the year 2000, Pip completed a Master of Business Administration (MBA), specializing in Business Administration and Management. Continuing their education, Pip obtained a Master of Public Policy from 2004 to 2005, with a field of study in Public Policy Analysis. Pip then pursued a Bachelor of Laws (LLB) degree, which lasted from 2007 to 2012 at the University of Tasmania. Finally, in 2013, Pip completed a Graduate Diploma in Legal Practice from the University of Tasmania.