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Billy Osterman has extensive work experience in recruiting and financial services. Billy started their career as an Intern at Sourcebooks in 2002. Billy later worked as a Recruiter at Staffing Now and CPS, Inc. In 2007, they joined LaSalle Network as a Recruiter and was responsible for recruiting various specialties. Billy then served as a Corporate Recruiter at Groupon and later became a Merchant Development Director. Billy joined Principal Financial Group in 2015 as a Financial Representative. From 2016 to 2019, Billy worked as a Senior Executive Search Consultant specializing in Tech Recruiting at Lucas Group. Billy currently works as the Lead Recruiter at Kin Insurance since 2019.

Billy Osterman completed their Bachelor of Arts degree in Rhetoric at the University of Illinois Urbana-Champaign from 1999 to 2003. Billy later attended Dominican University from 2009 to 2011, although the degree name and field of study are unknown.