The challenge-based learning (CBL) approach applied to real problems can lead to change by substantially impacting companies and organizations that offer challenges to be solved. This pedagogical approach can be used in open social innovation (OSI) processes. This innovative learning method leads to capacity building, soft skills or twenty-first-century skills acquisition, and experiential and active learning that connects students with companies, cooperatives, and Third Sector organizations. This chapter aims to understand how a challenge-based learning initiative such as the 8 ECTS “Social Entrepreneurship and Sustainability” curricular course at the University of Trento (Italy) impacts entrepreneurial and innovation processes on the companies involved in the educational initiative. Measuring the impact on challenge providers involves evaluating short- and long-term benefits and tangible and intangible outputs of the OSI. The research collects data from online questionnaires and semi-structured interviews with five challenge providers involved in the course through a qualitative methodology. From the challenge provider perspective, this course represents an opportunity to acquire new ideas and solutions, recruit young talents, and gain knowledge and competencies. This chapter aims to foster the literature gap and include theoretical and managerial implications.