Education is one of the eight Millennium Development Goals (MDG) of the United Nations. Considerable interest has been displayed in online education at scale, a new arising concept to realize this goal. Yet connecting online education to real jobs is still a challenge. This CHI workshop bridges this gap by bringing together groups and insights from related work at HCOMP, CSCW, and Learning at Scale. The workshop aims at providing opportunities for groups not yet in the focus of online education, exemplified by students who have not have equal access to higher education, compared to typical students in MOOCs. The focus is on theoretical and empirical connections between online education and job opportunities which can reduce the financial gap, by providing students with an income during their studies. The workshop explores the technological analogue of the concept of 'apprenticeship', long established in the European Union, and education research . This allows students to do useful work as an apprentice during their studies. This workshop tackles such questions by bringing together participants from industry (e.g., platforms similar to Upwork, Amazon Mechanical Turk); education, psychology, and MOOCs (e.g., attendees of AERA, EDM, AIED, Learning at Scale); crowdsourcing and collaborative work (e.g., attendees of CHI, CSCW, NIPS, AAAI's HCOMP).