TRAINERS
Oakside boasts a team of elite trainers renowned for their knowledge, experience and success in the sport.
Leah Curtiss - Head
Trainer
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Leah is a professional hunter/jumper rider and trainer based out of her Oakside, LLC in Bryan, TX. She maintains a small group of dedicated clients ranging from the Short Stirrup division to Grand Prix, while also continuing to compete herself in both national and FEI events.
Leah enjoyed a decorated junior career training under Holly Shepherd and David Pellegrini, with numerous top 10 finishes at the fall indoor shows, Devon, as well as national level Grand Prix competitions. Following graduation from Texas A&M University, Leah turned professional and relocated to Germany to work under Hamburg Derby winner Pato Muente.
Now armed with invaluable knowledge of flatwork, mechanics, and developing young horses, Leah started her own business, Oakside, LLC in 2017. In addition to continuing her successes
in the Grand Prix arena, one of Leah’s main goals is to continue developing riders for the highest level of the sport in the hunter, jumper, and equitation rings. Her students have enjoyed
success and numerous top 10 finishes at the prestigious fall indoor shows, Devon, USHJA International Hunter Derby Finals, as well as national Grand Prix competitions themselves. In
2023, Leah was part of the gold medal winning team at the USHJA Platinum Performance National Championships, as well as earning a silver medal individually. She also notched
fourteen other top 10 Grand Prix finishes across the country throughout the year. In the last two years, Leah has focused on developing young horses for the Hunter Derby rings, with numerous wins and top placings across several mounts. In 2026, she was named leading developing professional rider at the prestigious Pin Oak Charity Horse Show.
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Sidney Pleiss-
Trainer, Barn Manager
Sidney Pleiss has built her career in the hunter/jumper industry working alongside respected professionals including multiple-time FEI World Cup Finalist Jenni McAllister, Chenoa McElvain, and USHJA President Britt McCormick. Her experience has given her a well-rounded foundation in developing horses and riders, managing competitive show programs, and competing throughout the country.
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Sidney is passionate about developing confident, educated riders and creating individualized programs for each horse-and-rider combination. She places a strong emphasis on horsemanship, clear communication, and building a solid foundation for long-term success. Throughout her career, she has also helped numerous young riders achieve their goals of being accepted into collegiate equestrian programs.
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As a rider, Sidney has experience developing horses across the hunter and jumper disciplines and continues to pursue her own competitive goals, with aspirations of competing at the Grand Prix level and beyond.
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Above all, Sidney believes in creating a positive, competitive environment where excellent horsemanship and the well-being of the horse always come first.
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