In the Country with Dave Woods:
Jessie T

Growing up in Kingston, Ontario, Jessie found her love for performing by competing at local country fair singing competitions. Since moving to Kitchener in 2012, she has been headlining venues and festivals across Ontario, including Meadows Music Fest, Harrow Fair, Manitoulin Country Fest, JUNO Host City Music Exchange, Indie Week, Folk Music Ontario Conference, Canadian Music Week, and the Country Music Association of Ontario Awards. Jessie has played alongside some of the best in Canadian country music, including Dallas Smith, James Barker Band, Michelle Wright, Dan Davidson, Adam Gregory, Steve Wilkinson, and Beverley Mahood. Growing her resume as a background vocalist, Jessie is also a fixture in other recording artists’ bands, including Jason Blaine and Graham Scott Fleming.

In 2023, Jessie received a nomination for Kitchener-Waterloo Woman of the Year for her community work. She has served on judging panels for artist development competitions, including The Shot, has sat as a juror for the City of Kitchener Create and Connect Grant, guested as a songwriting mentor for Kitchener Library’s ImagineIt Songwriter series, and even hosted a songwriting mentorship clinic for Waterloo Long and McQuade.

Jessie’s busy 2025 touring schedule includes performances at Boots & Hearts Music Festival and Crooks Rapids Country Festival.

Congratulations on your nomination this year for Female Artist of the Year! Can you describe what this honour means to you?
Ontario is an insanely talented place. Being nominated by my peers to be an artist representing the scene feels like a big honour, especially as an indie artist. Most of these ladies I’m nominated beside are musicians I’ve crossed paths with at different points in my career. It’s inspiring to think about how much we’ve all grown since those moments. I’m looking forward to reminiscing and celebrating those journeys at this year’s awards.

This August, you’ll be performing at Boots & Hearts! How stoked are you for that performance?
Boots & Hearts was at the top of my “one day festival wish list”, so I don’t know if I have the words to describe how excited I am. I’m just stoked to bring the band and put on a killer show. Seeing some of my favourite bands share the poster with my name on it has been crazy, though and as someone who attended Boots ’ first year in Bowmanville, it’ll be a surreal “full-circle-moment” to be back there as an artist.

Which artists have inspired you over the years in your music career, and why?
Oh man – there are so many. Some musical influences that have inspired my sound are The Chicks, Sheryl Crow, Avril Lavigne, P!NK, Alanis Morissette and Carolyn Dawn Johnson, but honestly, my largest inspirations are my artist friends. Day to day, they’re out there grinding, working towards incremental success. They’ll drive thousands of kilometres playing back-to-back gigs to fund their own projects out of their own pockets, they write their own grant applications, they get creative with release strategies cause of working with limited resources. That is what’s truly inspirational to me – watching these people, despite all odds, still making it happen. It keeps me motivated, and I’m thankful to be a witness to the grind.

What songwriting advice would you give to a new artist who has just started writing?
I actually just hosted my first songwriting clinic. It was cool to sit and think about writing and what the process looks like when you dissect it. One Miles Davis quote stuck with me – “First you imitate, then you innovate”. Listen to songs that inspire you and learn to play/sing them. Then try to write songs LIKE that. Eventually, you will want to explore past those guidelines, and that’s where your real style starts to evolve. Also, determine your audience – who are you writing for? What is your idea of success for that song? All of these are important questions and will change which song you end up with.

You have said that your song “Just A Number” reminded you of why you started writing songs. Please share with us the inspiration behind that song.
One of the reasons I felt connected to country music as a genre was the songwriting. Country music told a story, and a lot of those songs helped me get through the trials of growing up. When I started writing, that was my goal: to write music that helped people. Just A Number is a diary entry. It’s my story about being a girl in the world and feeling my value was determined by the “numbers” society labelled me with, and in turn, how I was labelling myself. I brought this idea to Nicole Rayy and Elyse Saunders, and I’m thankful they trusted it enough to share their own experiences. It’s been humbling to hear other people’s stories about how Just A Number connected with them. That’s the music I want to continue to make.

What part of a music career do you find the most rewarding?
Writing a song people connect to or putting on a killer show.

Who is your dream duet partner and why?
Carolyn Dawn Johnson, Sheryl Crow or Stephen Wilson Jr.. All of these artists are badass and insanely talented musicians/artists. They inspire a lot of the music I make, so it’d be super cool to see what kind of song we’d create together.

And finally, what would you like to accomplish in your music career over the next few years?
I’m currently working on new music, and I’ve never been more proud of a body of work. These songs feel like a true extension of me, and I can’t wait to have them out in the world. I want to continue to write and release this kind of music and tour, for sure.

Check out Jessie’s fun music video for her song “I Can Be Your Margarita”