Osborne's directorial debut was the short film Feast (2014), about a Boston Terrier who loves getting fed junk food. The short was produced by Walt Disney Animation Studios and premiered in front of Big Hero 6 (2014) in theaters. It won the Academy Award for Best Animated Short Film in 2015.

Osborne had previously worked as an animator on films such as Wreck-It Ralph (2012) and Bolt (2008). Osborne's next project will be a 360-degree animated short film for Google's Spotlight Stories currently titled Pearl, about the relationship between a father and his daughter. The short film will be a musical set entirely inside a car.