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Heather Cunningham has over 17 years of experience in finance and operations. Heather began their career in 2003 as a Billing Specialist and Customer Care Specialist at Cross Country Automotive Services. Heather then progressed through the ranks to become a Financial Analyst, Senior Financial Analyst, and then transitioned to BEAUTE PRESTIGE INTERNATIONAL in 2007 where they held the roles of Financial Analyst, Finance Manager, Senior Manager, Finance, and Director, Finance. In this role, they directed the US fragrance division, managing two finance professionals in the execution of rolling monthly forecasts as well as monthly and annual closing processes. Heather was also responsible for annual budgets and 3 year strategic plans. In 2015, they joined ModCloth as Senior Director, FP&A. Most recently, they have been with Rocksbox since 2019, where they have held the roles of VP of Finance and SVP of Finance & Operations.

Heather Cunningham received their Bachelor's degree in Economics and Finance from Bentley University between 1998 and 2002. Heather then went on to earn their Masters in Professional Studies in Marketing & Management, Cosmetics & Fragrance from the Fashion Institute of Technology between 2012 and 2014.