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Drew Guillen has held various roles in the sales and marketing industry since 1999. Drew began their career at Qwest Communications as a Senior Account Executive, where they managed over 30 accounts with 40 or more employees. In 2003, they moved to Integra Telecom as a Senior Account Executive and achieved top sales for the year with 150% of plan. Drew then took a role at Hibu (formerly Yellow Book) in 2005 as an Account Executive, where they were responsible for selling new marketing programs both print and online for small to medium businesses. In 2008, they joined EMC (formerly Isilon Systems) as a Territory Development Representative, where they were responsible for supporting and assisting the field team in uncovering, creating and managing new opportunities/projects for Isilons' High End Enterprise Storage Technology solutions. In 2009, they moved to Rain, Inc as the Assistant Director of Sales and Marketing, where they created the sales force within the organization and utilized social media network to sell software to the real estate professional community. In 2013, they took a little over a year off to undergo intense training with a Pro/Grand Master pool player and became an Advanced Pool Player. Drew then joined American Poolplayers Association and won the National 8 Ball Championship in 2014, as well as the West Coast Regional Invitational in 2014 and the National 8 Ball Team Championship in 2012, 2013 and 2014. In 2016, they joined Avvo as an Account Executive and then moved to Solutions II in 2019 as an Account Executive, where they assisted clients to leverage technologies and services that drive the cost out of IT.

Drew Guillen attended the University of Washington from 1993 to 1998, where they studied Electrical Engineering. Drew then attended Kent Meridian High from 2001 to 2003, where they earned a High School degree.