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Oleg Ryaboy has extensive work experience in the technology industry. Oleg is currently the Chief Technology Officer at Protolabs. Prior to that, they worked at Digital River, where they held various roles including Chief Technology Officer, SVP and Vice President of Software Development and Architecture. Oleg was responsible for the engineering, product development, and technology strategy of Digital River's cloud SAAS e-commerce platform. Oleg also worked as a Senior Software Development Manager at CVS Caremark: MinuteClinic, where they directed all software development activities. Oleg was also the Lead Architect at CVS Caremark Corporation, where they led the IT Research and Development group. Before that, they worked as a Manager at Target Corporation, leading the development of software for their distribution centers. Oleg's earlier experience includes working as the Director of Engineering at Gearworks and as the Director and CTO at Ulysses netSolutions where they led the development of various large-scale web and client-server systems.

Oleg Ryaboy has a Bachelor of Science degree in Computer Science from the University of Minnesota, which they obtained from 1995 to 1997. Oleg also holds a Master of Science degree in Software Engineering and Business from Carnegie Mellon University, which they completed from 1999 to 2000.