Waterland first rose to popularity in 2013 with her satirical recaps of The Bachelor Australia, and is also known for her books The Anti Cool Girl and Every Lie I've Ever Told.

[citation needed] Waterland has been a contributing writer and actress on several Australian TV shows, most notably ABC's Tonightly with Tom Ballard and Channel Ten's Sisters.

She was also co-star and creator of ABC satirical political documentary series, What's Going On: With Jamila Rizvi and Rosie Waterland, which first aired in 2016.

[5] The Anti Cool Girl sold over 45,000 in its first few months in stores, making it one of the most popular young Australian memoirs in recent times.

[12] Waterland debuted her first live one-woman show at the Melbourne International Comedy Festival in March 2016, called "My Life On The Couch (with vodka)".

[13] Waterland's next one-woman show, Kid Chameleon, began touring nationally in February 2020, but was put on hiatus due to the pandemic.