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Heather O'Shea has a diverse work experience spanning over several industries. Heather began their career as the General Manager of Mick O'Shea's Irish Pub in 1995. After that, they worked as an Administrative Assistant at Eastern Sales & Engineering, where they handled electrical engineering services for petroleum stations and fast food convenience stores. Heather then transitioned to the role of Assistant Manager in the Uniforms Division at Guardian Fire & Safety, where they were responsible for supplying uniforms and equipment to fire and police departments, as well as other security companies.

Following their time at Guardian Fire & Safety, Heather joined Iron Mountain as an Account Manager. Here, they conducted sales and account development activities, including training, client visits, prospecting, and responding to RFPs. Heather also negotiated contracts with new and existing customers and prepared formal business reviews and proposals. After 11 years at Iron Mountain, they joined FedEx as an Account Executive, where they managed customer accounts.

In 2009, Heather became the Chapter Admin for NAIFA & SFSP - Richmond, supporting the organizations in administrative duties for 5 years. Heather then worked at DICK'S Sporting Goods as a Store Associate from 2013 to 2015.

In the same year, Heather started working as a Student Travel Consultant at NationsClassroom, a role they held until 2015. Concurrently, they also served as an Assistant Coach for the New World Sports Thunder/Storm RVA.

Heather's most recent role was at Automated Healthcare Solutions, where they started as an Account Manager in December 2015. In July 2016, they were promoted to Senior Account Manager. Their responsibilities involved delivering exceptional service, ensuring compliance with regulatory requirements, and maximizing customer utilization.

Heather O'Shea completed their education in a chronological order. Heather obtained a Bachelor of Arts degree in Liberal Arts from the University of Richmond, where they studied from 1997 to 1999. Prior to that, they earned an Associate of Arts degree in General Studies from Kaplan College, attending from 1991 to 1994. Heather also received their High School Diploma in College Prep from Maryvale Preparatory School for Girls, which they graduated from in 1991.