Jessie Prescott arrives in New York City, where she is dumped out of her cab at the Ross' luxury condo building (Fairfield) and meets a little girl named Zuri and the doorman of the Fairfield, Tony. Witnessing her nanny Kate running out hysterically, Zuri asks Jessie to be her new nanny. Refusing, Jessie passionately states that she came to New York to follow her dream. Taking it as a joke, Zuri kindly pulls Jessie upstairs, saying how she likes her food. Jessie meets Bertram, a sarcastic, lazy butler, and adoptive parents, Morgan and Christina Ross. They hire her to be the nanny to Zuri, Ravi, Luke, and Emma. After initially failing to win over each child, they attempt to run away. She soon makes up her mistakes to each child except Emma, who is upset that her parents cannot attend her science fair. Jessie flies the Ross' helicopter to the movie set in Chicago where Morgan and Christina are telling them that they need to spend more time with their children, as their presence is important in their lives; this move gets her fired. Nevertheless, she attends Emma's science fair to support her. However, Emma's parents show up to the science fair as well, having taken Jessie's advice. In the end, Emma wins the science fair and Jessie is rehired. Each child attempts to give Jessie another chance.
- Debby Ryan as Jessie Prescott
- Peyton List as Emma Ross
- Cameron Boyce as Luke Ross
- Karan Brar as Ravi Ross
- Skai Jackson as Zuri Ross
- Kevin Chamberlin as Bertram Winkle
- Christina Moore as Christina Ross
- Chris Galya as Tony Chiccolini
- Brian Carpenter as Head Judge
- Bryan Okes as A.D.
- Charles Esten as Morgan Ross