Jessie Jo Dillon was always going to have a career in music. With a dad in Country Music Hall of Fame and a mom entrenched in the world of A&R, Dillon’s GRAMMY-nominated career is no suprise.
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That doesn’t mean it came easily, though. Speaking to American Songwriter, Dillon shared how she “hustled really hard” to forge her own path, one that includes penning hit songs for artists including Maren Morris, Jelly Roll, and Keith Urban.
While co-writing George Strait’s “The Breath you Take” in 2010 first made Dillon feel like she was “doing something right,” it was he work on Cole Swindell’s 2018 track “Breakup in the End” that made her realize that people were connecting with her musical perspective.
“With the artists, I definitely think I’ve had a good career so far because I am such an artist-forward person and writer,” she said. “I think they have the hardest job in the world. It’s really important to me when I sit down with them, not to be a person that’s like, ‘Let me write you a hit!’ I want to know where they’re at, what their perspective is.”
Jessie Jo Dillon’s Recent Songwriting Successes
That has proven to be a winning strategy in the years since, as Dillon has continued to write with country music’s biggest stars. One such artist is Megan Moroney, with whom Dillon worked on Am I Okay?
“She’s not only a brilliant writer, but she’s so smart about her business and her branding. I feel like I’m always learning from her about those things,” Dillon said. “… It’s always just fun with her. I feel like she and I have a very similar process. It’s kind of just effortless with her in a way.”
Then there’s Russell Dickerson for whom Dillon co-wrote “Happen to Me,” an instant smash that he’s since re-recorded with the Jonas Brothers.
“As soon as the song started picking up the crazy amount of steam, I don’t think any of us could believe it. We were like, ‘Holy s**t,’” Dillon recalled. “And then, it just kept getting crazier. Now to have a song with the Jonas Brothers featured on it is just absolutely mind blowing.”
Also of note is Dillon’s work with Kelsea Ballerini. From the title track on Patterns to the Mount Pleasant standout “People Pleaser,” Dillon and Ballerini’s partnership is one that led to some incredible songs.
“She was born to do this—write songs, be a performer, even be a famous person. She is kind of a thoroughbred to me in that way,” Dillon said. “… She’s so honest in her songwriting, and she’s never scared to stay things that maybe somebody else would be. She’s always just gonna go for the heart of the matter.”
What’s Next for Jessie Jo Dillon
It’s no surprise that, with a resume like that, Dillon recently earned her third consecutive nomination for Songwriter of the Year, Non-Classical at the GRAMMYs.
“There’s really nothing like it,” Dillon said of being GRAMMY-nominated. “I love the Recording Academy and what it stands for so much. I have since I was a little kid. And so, to be in three times in a row, I can hardly even grasp that… It’s kind of beyond me.”
It’s not just songwriting that’s been taking up Dillon’s time as of late. In August, Dillon launched Gatsby Records as Founder & President. The MCA imprint released Carter Faith’s debut LP, Cherry Valley, back in October.
“I think she is such a special artist and singer,” Dillon said of Faith. “There’s nobody like her in the landscape to me right now. She’s like a little unicorn to me. I cannot wait to see what all 2026 brings for her.”
Now, Dillon is bringing all of her experience to American Songwriter. She’s set to serve as the 2026 Lyric Contest Dream Mentor.
“I just always wanna try and lift other people up that love music and are writing songs, because I definitely know that I always had great people around me, lifting me up,” she said. “It just felt like a really cool thing to get to be a part of.”
For those entering the contest, Dillon has just one piece of advice: “Be true to yourself.”
“I think that it’s easy to get caught up in… trends or what is going on currently in like the market,” she said, “but I think if you always say true to your inner voices, that’s when you get the best music.”
Photo by Libby Dansworth
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