Kai Enslin joined the Charlton academy at U13 level having impressed while on trial with a stunning goal against Crystal Palace.

Primarily a right-sided attacking player who likes to cut in on his left foot, Enslin contributed to the U18s' Professional Development League Two - South title victory in the 2022/23 season.

Having signed his first professional deal in June 2023, Enslin went on to play a vital role in another PDL2 - South title win in the 2023/24 campaign, this time also operating at left-back from time to time.

In November 2024, he made his first-team debut in the Addicks' Bristol Street Motors Trophy tie with Bromley at The Valley.