middlebury-college
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Nick Wilkoff
Nick Wilkoff is the Chief Marketing Officer of L.L.Bean, the 111-year-old Maine outdoor brand known for its lifetime guarantee, Bean Boots, and Outdoor Discovery programs. A Middlebury environmental policy graduate who started his career as a Forrester Research analyst, Wilkoff leads brand, marketing, and customer engagement for a company doing roughly $1.7 billion in annual revenue. He champions an outdoors-for-everyone philosophy, pairing L.L.Bean's heritage of quality and durability with a modern, inclusive, community-first approach to keeping a legacy brand relevant.
Kate Condliffe
Kate Condliffe is the co-founder and CEO of Diana Health, a network of women's health practices that partners with hospitals to rebuild their maternity and OB/GYN programs around holistic, team-based care. She launched the company in 2020 out of AlleyCorp's healthcare incubator after two decades scaling high-value care models, including roles as COO of the Clinton Health Access Initiative and COO of the birth-center network Baby+Co. Under her leadership, Diana Health has grown to nine locations across Tennessee, Florida, and Texas, cares for more than 80,000 women annually, and has raised roughly $101 million to date, including a $55 million Series C in 2025.
Garrett Dodge
Garrett Dodge is the Co-Founder and CEO of Rockbot, the business media platform that powers music, TV, digital signage, and advertising for nearly 50,000 brick-and-mortar locations across North America. Founded in 2010, Rockbot has grown into a $9.2M revenue company serving major brands including Planet Fitness, Walmart, Shake Shack, and JetBlue, backed by Google Ventures, Universal Music Group, and others. Dodge holds a B.A. from Middlebury College and an MBA from MIT Sloan, and previously helped build Caesars Entertainment's Innovation Team before channeling that experience into reimagining how physical spaces use media to engage customers.
Emily Bennett
Emily Bennett is an Investment Partner at Andreessen Horowitz, where she leads investing for a16z speedrun - the firm's high-velocity startup accelerator that has deployed over $180M to 150+ startups since 2023. A neuroscience graduate of Middlebury College (magna cum laude) turned Harvard MBA, she carved a winding path through product roles at Spotify, The New York Times, and Facebook before pivoting fully into venture at Owl Ventures, where she rose to Partner with a focus on edtech. At a16z, her investment thesis centers on AI-native tools that allow single founders to operate what once required entire teams, and she is a vocal advocate for the first AI-native university - an institution where learning paths, schedules, and research adapt in real time through continuous data feedback loops.