Barry Finder

Barry Finder is the senior-most operational leader of Chegg Skills, where he oversees instructional design, content development, product marketing, student support, business operations, partnerships, and quality assurance. He leads cross-functional execution and learning strategy for scalable, outcomes-driven programs designed for working adults. Barry’s commitment to educational access began early. As an undergraduate at Wesleyan University, his high honors thesis examined how structural inequality restricts access to elite higher education and how institutions unintentionally perpetuate class-based barriers. He later earned a master’s degree in cognitive science, studying the relationship between language, thought, and cognitive development. That foundation shapes his belief that learner variability is not a deficit to remediate, but a design constraint to build for from the start. Before Chegg, Barry spent nearly six years at Uber, where he led large-scale field operations across the U.S. and Canada. He saw firsthand how flexible work could function as an engine of economic independence for drivers balancing caregiving, second jobs, language barriers, or nontraditional schedules. He also managed large frontline teams supporting these drivers — teams that looked a lot like the learners Chegg Skills serves today: ambitious, time-constrained, and navigating structural friction. At Chegg Skills, Barry brings together cognitive science, operational discipline, and deep empathy for nontraditional talent. His team designs accredited and non-accredited pathways that meet learners where they are — whether they are busy working parents, career switchers without sociocultural capital, or neurodivergent learners navigating asynchronous environments that were not built with them in mind. He believes technology, when grounded in science and compassion, can be a powerful equalizer — extending access from classroom to career. Under his leadership, Chegg Skills has built a genuinely learner-first model that drives category-leading outcomes in async-heavy online programs, helping learners of diverse backgrounds break through the “paper ceiling” and translate potential into opportunity.