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Raewyn Cummings has extensive work experience in project management and exhibition delivery. Raewyn started their career in 1985 at Fay Richwhite, where they worked in settlements and later became a publisher. In 1990, they joined Mesa Design Limited as a Director, overseeing graphic production management. In 1996, they worked as a Graphic Production Manager at Te Papa on a contract basis, managing the production and installation of graphic content for the museum's opening. From 1999 to 2001, they worked as a Graphic Production Manager on contract at the National Museum of Australia.

In 2011, Raewyn joined the Museum of New Zealand Te Papa Tongarewa, where they held various roles. Raewyn served as the Manager of Project Delivery from October 2011 to March 2013. Raewyn then became the Programme Development and Delivery Manager from April 2013 to May 2016. From May 2016 to September 2019, they worked as the Programme Manager Exhibitions, overseeing the redevelopment of the Natural History exhibition zone and managing the temporary exhibition portfolio. In April 2018, they briefly took on the role of the Acting Manager of the Project Management Office, responsible for project governance and strategy. Finally, since September 2019, Raewyn has worked as the Head of Exhibition Delivery, leading the exhibition team at Te Papa.

Raewyn's work experience demonstrates their expertise in project management, exhibition delivery, and graphic production management.

Raewyn Cummings completed a Master of Business Administration (MBA) degree in Business Administration and Management, General from Victoria University of Wellington from 2016 to 2018. Prior to that, they attended Massey University, where the specific degree they pursued is unknown, but it was related to technology. Additionally, Raewyn studied photography at Victoria University of Wellington, though the duration of this study is unknown.

In terms of certifications, Raewyn obtained various qualifications. In 2019, they received Agile Team Facilitation certification from ICAgile. In 2016, they completed Training for Health and Safety Representatives from Business Central NZ. In 2015, Raewyn obtained PRINCE2 Practitioner and ICAgile Certified Professional certifications from APMG-International and ICAgile, respectively. Raewyn also completed PRINCE2® Foundation and Practitioner Certification Training from APMG-International in the same year. In 2013, they achieved MSP Foundation and Practitioner certification from APMG-International. The exact month and year of the Health & Safety - Stage One certification from ACC ThinkSafe is unknown.