Previous work (Chase et al., 2020) has shown that peer leaders in Peer-Led Team Learning (PLTL) programs not only experience immediate benefits to their learning and success as students, but also have lasting impacts throughout their career from transferable skills gained. This quantitative study builds on this work by examining the influence of past peer leader experience in one's current position as well as the impact of various program attributes such as training (frequency and format) and skill gains. These skill gains include coping with challenges (such as not having the correct answer), leadership, collaboration/teamwork, self-confidence, and problem-solving. A quantitative survey, developed based on semi-structured interviews from our previous work, was sent out to past peer leaders. Leaders who identified as underrepresented minority (URM) or Other were more likely to experience gains in all transferable skills in their current positions, except for coping with challenges. Being a peer leader in cyber Peer-Led Team Learning (cPLTL) predicted higher gains in all transferable skills, while more frequent training predicted increased gains in problem-solving skills. The number of years since being a peer leader negatively predicted gains in problem-solving. Gender and training format did not significantly predict gains in any of the skills.