In the second episode of the third season, it's clear that Roman positioned himself as an apprentice to Gerri. This is an alliance that could pan out well for him if he has hopes of becoming CEO. Even though Roman can't completely trust her (she's got a stake in the game as well), he seeks out her advice about switching to Kendall's side in the Roy family civil war. Her answer: "Stick with me, Roman." She didn't say stick with your father or stick with the company. Instead, she said, "Stick with me."
Roman's Odds: Medium
This can go two ways. Either dynamic duo Roman and Gerri take over Waystar Royco together, or Logan hands the CEO position to his son. At the end of the most recent episode, Roy calls Gerri "the heart of everything through this sh*it storm, but wearing a full chemical and biological suit." Gerri is clearly a formidable opponent that can bring Logan down and put her partner in crime, Roman, at the top if she puts her mind to it. Or there's a chance Logan chooses his son as the next CEO somewhere down the line. After all, Roman did score extra points from daddy for spying on Kendall and Gerri.
Image Source: HBO / Macall B. Polay