Exposition
One day, team RWBY went into a hunting trip during one of its assignments for Beacon and returned successfully.
Well..all except one..
Ruby was separated from her team. It was an ambush planned by Cinder and her cohorts to capture Ruby and it worked flawlessly. They tortured Ruby for days but got nothing out of her. The only person who didn't take pleasure in the torture was Neo and in one night later released Ruby from her chains, gave her Crescent Rose and gave her directions to escape from the White Fang hideout she was in.
Ruby followed through and Neo aided her in the last moment by misdirecting the guards outside to another direction. Ruby thanked Neo and promised to repay the favor one day.
Ruby is free but she started thinking where would she go? She could go back to Beacon which is the easiest solution but she chose a different path...quite unlike her.
She decided to become a mercenary for a living.
At first, she would just take Huntress like jobs by taking a contract to clear out a place full of Grimm. They paid fair and Ruby was able to make a living through budgeting but she knew that she needed a place to stay, renting places isn't exactly cheap and she had her own expenses to think about.
For Ruby's friends, they found no trace of her everywhere and felt guilty for not noticing it sooner. They became more withdrawn and barely keeping up in classes. In the back of their minds, they hoped that Ruby is safe...wherever she was and that she would come back to them.
Ruby took some jobs involving humans next, some of which she wasn't proud of and shall not be spoken in this story but she did do a contract from a husband bartender who hired her to avenge his dead wife by killing some named -shall not be named- White Fang members who killed his pacifist wife while he was away. He thanked her, gave her some lien and told her that a certain handler is waiting to meet her and gave her the location. She nodded in reply and left to find that handler.
This begins the story of Ruby Rose who instead of becoming a Huntress, she becomes a Private Contractor.