Eighteen-year-old Cailey has dreams of becoming one of the few Black female commercial pilots in the country. Her mother Sherie has worked hard and taken out loans to afford her daughter's pilot lessons. Kelly brings them on the show along with two pilots from Sisters of The Skies, an organization that has mentored Cailey and is working to increase the number of Black female pilots in the country. Sisters of the Skies rewards Cailey with an amazing mentorship opportunity, but that not all! Boeing steps in and gives a $10,000 donation to Sisters of Skies and a $50,000 scholarship to Cailey.