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Courtney Woosencraft began their work experience in 1998 at Holiday Inn as a Customer Service representative. Courtney continued in this role until 2003 when they joined New Contracting as a Recruiter. In 2006, Courtney joined SECURA Insurance as a Customer Service Representative for Personal Lines. In 2011, they transitioned to the role of Underwriting Service Specialist for Commercial Lines at SECURA Insurance.

Courtney Woosencraft obtained a Bachelor of Arts degree in Communications from St. Norbert College, where they studied from 1996 to 2000.