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Caleb Woods has held a variety of roles in the software industry since 2006. In 2006, they began as a Marketing and Information Technology Intern at Cornerstone Home Loans. In 2009, they joined CollegePlus! as a Software Development Manager, Systems Architect, and Business Analyst. In 2012, they joined RoleModel Software as Chief Executive Officer, CTO, and Software Craftsman. As CEO, they developed the team and technology vision, while as CTO they led the expansion of the company's technical and design craftsmanship services delivery capabilities. As a Software Craftsman, they worked with clients to solve their business problems and led Agile teams with tight feedback loops.

Caleb Woods attended Thomas Edison State University from 2009 to 2010, and obtained a Bachelor of Science in Business Administration with a field of study in Computer Information Systems.