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Hannah Checkley has a diverse work experience in the legal field. Hannah is currently working as a Legal Counsel at Garrison since May 2023. Before that, they served as a Legal Counsel at Cogo from June 2022 to May 2023. Prior to that, Hannah worked at Duncan Cotterill as an Associate from September 2020 to June 2022. Hannah also had multiple roles at Quigg Partners, starting as a Solicitor from June 2015 to March 2018, then as a Senior Solicitor from April 2018 to June 2020, and finally as a Senior Associate from June 2020 to September 2020. Hannah began their legal career at Terrace Chambers as a Law Clerk from November 2013 to June 2015.

Hannah Checkley completed their high school education at St. Margaret's College in Christchurch from 2005 to 2009. Hannah then pursued their bachelor's degree in Law and Arts at Victoria University of Wellington, graduating in 2014. Their field of study during this time was Law.