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Bobby Dolan has a diverse work experience spanning over several companies and roles. Bobby is currently working as a Content Creator at Almost Friday Media since December 2021. Prior to this, Bobby worked at Dollar Shave Club from 2015 to 2021, where they served as a Social Media Manager, Social Media Coordinator, and Member Services Associate. Bobby also has experience as a Business Associate at LivingSocial in 2014, where they created new partnerships and handled sales activities. At TaylorMade-adidas Golf, Bobby worked from 2011 to 2014, initially as a Sales/Service Specialist and later as a Marketing Intern in 2010. In 2010, they also had a role as a Program Coordinator Intern at Casey Cares Foundation. Earlier in their career, Bobby worked as a Caddie at The Members Club at Four Streams from 2004 to 2010.

Bobby Dolan attended Towson University from 2006 to 2010, where they earned a Bachelor's degree in Business.