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Leah Kowalewski has had a diverse work experience, beginning with volunteering at the Greater Boston Food Bank in 2005. Leah then worked as a Senior Bartender at Rock Bottom Brewery from 2003 to 2011. During this same period, they were an Intern at SmashFly Technologies in 2011. Leah then worked as a Senior Bartender at 5 Napkin Burger from 2011 to 2013. In 2013, they began working at Wayfair LLC as a Business Account Manager and at Brafton Inc. as an Associate Lead Generation Executive. In 2014, they were an onDemand Representative at Lionbridge. From 2015 to present, they have held various roles at Invaluable, including Senior Director of Sales - North America, Director of Sales - North America, Senior Manager North American Advertising Sales, Senior Account Manager, Team Lead, and Account Manager.

Leah Kowalewski attended UMass Boston from 2008 to 2011, and obtained a bachelor's of arts in Psychology in 2011.