Freeride Snowboard Coaching

based in Golden BC

Sideways Strategies offers competitive coaching for athletes aged 9–18 who want to push their freeride performance, as well as private coaching for riders of any age looking to sharpen their skills. Whether you’re training for your next competition, riding with Jessie on event day, or booking a one-on-one session to master new tricks and big-mountain techniques, you’ll get personalized, experience-driven coaching from a seasoned freeride veteran with years of competition success and decades of backcountry filming. From terrain-reading and safe line choice to creative tricks and flow, Jessie brings the insight, passion, and energy to help you ride with more confidence, style, and fun.

Independent Athlete Freeride Coaching

Rider: Devun Perry - Photo: Oatway Productions

Join seasoned freeride veteran Jessie Oatway to build confidence, strength, and playful style on the mountain. Whether you’re working on popping higher, tweaking grabs, exploring rotations, mastering butters, or other fun snowboarding antics, every session is tailored to your riding level and experience.

You’ll develop terrain-reading skills for all conditions, learn the hazards of big-mountain riding, and practice safe riding techniques. Jessie will guide you through line-scoping strategies so you can move around venues with ease, choose smart lines, and know when and where it’s safe to push your limits. You’ll also learn how to make the mountain work for you—riding with less effort and more flow.

Athletes can choose from event-only coaching, pre-event training days, or a full package combining both. Whether you want Jessie by your side at competitions offering on-the-ground guidance, or in training sessions to fine-tune your skills ahead of time, you can build the coaching plan that fits your goals.

With years of freeride competition experience and decades of backcountry filming, Jessie brings a rare combination of first-hand knowledge and creative vision. He takes pride in sharing his passion and expertise to help riders progress safely while keeping the joy of snowboarding front and center.

Private Coaching Session

Rider: Jessie Oatway - Photo: Maur Mere

Spend a day on the mountain with local snowboard pro Jessie Oatway in a one-on-one coaching session tailored to your riding goals. Jessie will share his passion, local knowledge, and years of big-mountain experience to help you refine your skills and ride with more confidence.

Riders should already be comfortable riding, carving, stopping, and navigating big-mountain terrain. If you are new to riding or want to learn how to snowboard, please book a lesson with our local mountain. This is not a learn-to-ride program.

Coaching sessions take place at Kicking Horse Mountain Resort and are available December through April.

Coaching at other locations is available—additional travel expenses will apply.

* Lift tickets are required