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Josh Lamberg's work experience begins in 1996 when they were a student at the University of Richmond. From 2000 to 2003, they worked as a Professional Baseball Player in Minor League Baseball. In 2003, they transitioned to the role of Senior Marketing Representative at Philadelphia Insurance Companies, where they worked until December 2005. From December 2005 to May 2006, they served as an Account Executive - National Sales at Liberty Mutual Insurance. In May 2008, they founded and became the CEO of Lamb Financial Group, a niche-focused retail firm in the non-profit and healthcare sectors. Josh held this position until February 2018. Josh then joined Lamb Insurance Services as the Chief Executive Officer in May 2008, a position they currently hold. Lastly, in November 2021, they became the CEO of Signers National.

From 1996 to 2000, Josh Lamberg attended the University of Richmond and earned a Bachelor of Arts (B.A.) degree in Rhetoric and Communication.