Bob O’Connor is a three-time software company CEO, founding two companies and later serving as CEO of Loftware, a global supply chain software provider. He began his career by teaching high school science and math before transitioning to his software career. O’Connor has continued his passion to support education by serving as a Trustee for Canterbury School in Connecticut for 14 years, as a member of the Winchester, Massachusetts, School Committee for six years, and currently as trustee for the Winchester Foundation for Educational Excellence. He has established two endowments to support teacher professional development. He holds a bachelor’s degree from Georgetown University and a master’s from the University of Connecticut.