Every mission, activity, and challenge you complete in GTA Online will net you Reputation Points (RP). This RP is essentially experience points that will increase your overall Rank. In order to reach Rank 100, you will need to gain just about 1,584,350 RP. It is recommended to complete as many Jobs and activities available whenever you are playing online in order to net a good amount of RP during your session.
In other words, as soon as Lester, Martin, or any other NPC calls you with a job, do not ignore it! Also, it's worth mentioning here that playing with fellow crew members and full lobbies will net a little more RP than usual at the end of an activity. Since most of the great RP-grinding methods from the Xbox 360 version of the game have been patched, this achievement will take a very long time in obtaining legitimately.
Unfortunately, many of the low-ranking jobs players will receive are short and do not offer that much RP. Despite this truth, it is absolutely necessary to complete as many jobs as possible until the more rewarding ones, such as Coveted (unlocked at Rank 36) and Rooftop Rumble (unlocked at Rank 75), are available. Once you reach these ranks, the aforementioned missions can be started by performing the following steps: Pause > Online > Jobs > Host Job > Missions > Coveted/Rooftop Rumble.
As mentioned, this achievement will require plenty of dedicated hours of playtime. Some of the jobs may get extremely tedious if you decide to perform the same one over and over again, so try varying your activities to help unload the stress involved with this achievement.