For this achievement you'll have to jump across the Orange cones on the map Roadside. However you won't be crossing the street, you'll be jumping parallel to the street. It should be around 20 cones long.
To get this, load up a game on Roadside by clicking the "create room" button on the "play" section. Select only the map Roadside, make it a Private match, and disable bots. This should allow you enough time to cross the cones.
It took me around 10-15 falls to get the feel of jumping from one cone to the next, so if you are struggling keep at it.
Also here is an old video of the beta, that helped me understand what to do. All credit to
1ofWiisdom for the video.