Drennen and Rosensweig

HWS News

19 January 2026 • Alums Leadership Lessons from the C-Suite

President and CEO of Chegg Dan Rosensweig ’83 and Professor Tom Drennen will coteach a management course where students learn directly from people leading some of the world’s biggest and most influential companies, from ESPN and Nike to Meta and Verizon.

This spring, students in “MGMT 305: Leadership and Learning in Entrepreneurial Values” will step into a classroom that looks less like a lecture hall and more like a company’s top-tier of executives, C-suite. Cotaught by Professor of Business and Entrepreneurship Tom Drennen and global business leader Dan Rosensweig ’83, the course invites students to explore entrepreneurship as a way of thinking, deciding and leading in complex environments.

Each week an astounding lineup of special guests will meet with students to share the ideas and decisions behind the industries that have shaped the world.

Speakers include tech executive Sheryl Sandberg, producer Brad Falchuk '93, L.H.D. '14, former Twitter CEO Dick Costolo, climate entrepreneur and musician Adam Met, singer-songwriter and mental health advocate Jewel, rapper MC Hammer, WNBA players Breanna Stewart, Napheesa Collier, Lexi Hull and Cam Brink, investor Ashton Kutcher, and top executives from organizations including Adobe, CLEAR, Eli Lilly, ESPN, Moxxie Ventures, Nike, Rent the Runway, The Skimm, Yumi and Verizon.

Rather than focusing on theory alone, Drennen explains, the course is built around learning from people who have navigated pivotal moments in their industries and careers. Students are expected to research each speaker in advance, craft meaningful questions for their visit and reflect afterward on how the conversation challenged their assumptions or reshaped their thinking.

Rosensweig

President and CEO of Chegg Dan Rosensweig ’83

Rosensweig brings senior leadership experience from some of the most influential, fast-growing companies in technology and media. He is the president and CEO of Chegg, and previously held senior leadership roles at Yahoo, CNET, ZDNet and Guitar Hero. A longtime supporter of HWS, Rosensweig has returned to campus often since graduating in 1983, including as the featured guest at a President’s Forum discussion “From Sherrill Hall to Silicon Valley.”

“What has impressed me most about Dan’s preparation for this course is his discernment about what students can learn from each guest,” Drennen says. “Take Ashton Kutcher, who studied biochemical engineering, made a dramatic pivot into acting, and then continued to reinvent himself again and again. He was never static. The lesson for our students is you have to keep evolving if you want to survive in business.”

The course culminates in a team-based venture pitch, where students develop and present a business idea informed by lessons from the semester and ultimately pitch it to Rosensweig. Additionally, students will complete a personal strategy statement, where they will articulate the values and principles they want to carry forward into their careers, especially when the landscape keeps changing.

“It’s the advantage of a liberal arts education. Our course objectives prepare students to apply critical thinking, creativity, ethical reasoning and strategic problem-solving to challenges,” Drennen says. “In the modern workforce, especially in the era of AI, these skills will be a huge differentiator.”  

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