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Jeff Siegel has a diverse work experience spanning over several decades. Jeff started their career as the Sales and Marketing Manager at WKMG News 6 in 1994. Jeff then joined ESPN in 1996 and held various roles, including SVP of Media Sales & Marketing and SVP of Affiliate Ad Sales, Marketing, New Business. During their time at ESPN, they were responsible for generating revenue exceeding $500 million. In 2009, they joined Ensequence as the SVP of Sales and Marketing. In 2010, they moved to TiVo as the SVP of Global Media Sales & Marketing, where they built and managed a global team and developed the world's largest smart TV ad network. In 2014, they became the CEO of Media Lodge, where they developed digital advertising solutions and managed over 35 websites. In 2018, they founded Avid Outdoorsman Media Group, where they served as the CEO until its successful exit in 2022. Presently, they hold the position of Chief Executive Officer at BitRail.

From 1989 to 1993, Jeff Siegel received a Bachelor of Science in Business Administration (BSBA) degree with a focus on marketing from John Carroll University.