[4][5] Jackson began her career as a child model, appearing in numerous national commercials, including for Band-Aid, Coca-Cola, Pepsi, and Old Navy.

[6] Jackson's first major acting role was in the 2007 independent film Liberty Kid, which was followed by a guest appearance in a 2008 episode of Rescue Me.

In 2009, Jackson made a cameo in the film The Rebound, and was cast as Little Fish in the Nickelodeon pre-school animated series Bubble Guppies.

She followed this with minor roles in the television series Team Umizoomi, Royal Pains and Boardwalk Empire, and the 2011 films Arthur and The Smurfs.

In 2019, she appeared in the music video for Lil Nas X's "Panini",[15] which went viral and spawned several memes due to her character being unable to escape the rapper.

[16] In 2019, Jackson made her writing debut with the book Reach for the Skai: How to Inspire, Empower, and Clapback,[17][18] and began voicing Summer on the Netflix animated series DreamWorks Dragons: Rescue Riders, which ended in 2020.

[20] Also in 2023, Jackson received scrutiny for hosting a $5 raffle with a MacBook as a prize through CashApp, and was accused her of scamming her followers in order to gain money.