Dan Rosensweig

Dan Rosensweig: President and CEO, Chegg

Dan Rosensweig, Dane Holmes

Dan Rosenzweig leveraged a serendipitous net gain from his first layoff at Pitney Bowes to navigate a career defining the shift toward direct-to-consumer technology sales and later as Yahoo's COO, where he missed a pivotal opportunity to acquire a then-unprofitable Facebook. Following that tenure, he founded Chegg to address the higher education crisis marked by $1.5 trillion in student debt and obsolete four-year degree models, advocating for an on-demand, skills-based system aligned with employer needs. His work highlights the urgent need to reform curriculum and enrollment barriers to serve non-traditional learners and resolve the financial stagnation facing millions of American graduates.