There are two new faces heading to Highway 65 Records in the concluding half of Season 5 of Nashville and we have your first look at both!

CMT announced in March that it was adding The O.C.'s Rachel Bilson and Empire alum Kaitlin Doubleday to the cast. Now we know exactly how they'll fit into the fold when the show returns in June, picking up about 10 weeks after the death of Rayna Jaymes (Connie Britton).

Doubleday will be playing country singer Jessie Caine, who left Nashville years prior "under a cloud of scandal" and has returned to reclaim her career and get custody of her son back. Rayna was a mentor to Jessie in the past, so Jessie has formerly crossed paths with Deacon (Charles Esten) and Scarlett (Clare Bowen).

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"We were interested from the beginning in talking about the different struggles singer-songwriters have," showrunner Marshall Herskovitz tells TVGuide.com. "Kaitlyn's character is someone whose life was essentially blown up. ... Some terrible things happened to her and really in some ways changed her forever, and she left town for a while. ... She's essentially trying to win back both her son and her career. So, we're watching someone trying to overcome what she perceives to be her own failings, and find a way back to the life that is meaningful for her."

Kaitlin's struggle is something that Herskovitz hopes viewers at home can relate to, especially during troubled times.

"When she's first introduced, it's in a writers in the round sort of thing, where different songwriters play at the Bluebird [Cafe]. She says, 'I used to be a singer but I left town to ruin my life.' And somebody else says 'Join the club,'" he explains. "There is this thing in country music where there's this understanding that people are so flawed. ... So much of American society is about hiding your flaws, corporate America. People don't talk about their weaknesses in general. They hide their weaknesses. But in country music, it's just right out there for everybody to see. And you really feel that in Nashville. We just found it interesting to explore a character like that, who is fundamentally driven and strong, who allowed bad things to happen and is trying to recover from it."

On the opposite end of the spectrum, Bilson's character Alyssa Greene is a fish out of water when it comes to country music. She is "a Silicon Valley marketing expert who is brought in to take Highway 65 to the next level." You won't find any Garth Brooks albums in her collection because she's not a country music fan -- something she's not afraid to admit. That doesn't matter very much to her though, because Alyssa is only there to "break through the old models and win through disruption." Her kryptonite? Having to show vulnerability in business and relationships.

"There's some real interesting stories that are going to happen about Highway 65 and what changes they need to make in order to stay alive. That's where Rachel's character comes in as the chief strategy officer," Herskovitz explains.

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"It's really fun to have a character who knows nothing about country music, nothing about Nashville," he continues. "It's such an inside baseball show, and to have somebody who just doesn't get any of it and who knows she doesn't get it, allows for some really interesting writing, because we're watching her discover so many things about - not so much the business, but the culture of Nashville, what country music is about, also how artists live their lives."

Surely not having any country music experience -- or love -- is going to cause problems with Alyssa and the artists she's coming in to represent, right? Not necessarily.

"She plays a character who is really good at getting along with people," Herskovitz says. "She's a bit of a cheerleader, and someone who is a peacemaker. ... There's an interesting dynamic within this character where her first aim is to have everybody get along. But that's not always possible in this world."

Check out a teaser for the rest of the season above.

Nashville returns June 1 at 9/8c on CMT.