Conversation with Stefan Claypool '09, Senior Principal Product Manager at Toast

Stefan Claypool graduated from Middlebury College in 2009 with a joint major in Economics and Chinese. He is a Senior Principal Product Manager at Toast, where he works on AI-focused products serving restaurants and the broader hospitality industry. Earlier in his career, he held roles at PayPal and Autodesk. He earned his MBA from Cornell University’s Johnson Graduate School of Management in 2013.

With a liberal arts background, Stefan navigated a non-linear path into the technology sector by focusing on business impact and developing a strong bias toward execution. He is particularly interested in helping liberal arts students understand how to position themselves for meaningful roles in fast-moving industries. His mentorship emphasizes practical career leverage—translating a broad academic foundation into durable professional skills, making thoughtful early-career bets, and staying adaptable amid rapid technological change.

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