Equestrian Training Team | Five Star Equestrian

At the heart of Five Star Equestrian is a dedicated staff whose expertise and passion set us apart in the Pleasanton equestrian community. Our trainers, led by Leah Feliz and Cassandra Keith, bring together decades of specialized experience in both endurance riding and Hunter/Jumper competition. This rare partnership means every student benefits from a blend of technical horsemanship and competitive insight, allowing us to support beginners, advanced athletes, and families who seek more than just recreational riding.

We are not a trail ride stable. Instead, our team’s focus is on structured skill-building, safety, and preparing riders for success in the ring. Every lesson, camp, and training session is guided by our commitment to building confident leaders, both on and off the horse.

Five Star Equestrian’s core strength lies in the partnership between Leah Feliz and Cassandra Keith. Leah’s lifelong background in endurance riding brings a technical, analytical approach to horsemanship, emphasizing the importance of communication, biomechanics, and safety. Cassandra grew up immersed in the Hunter/Jumper world, with a sharp eye for competitive performance and a deep understanding of what it takes to succeed at the highest levels. Their collaboration began when Leah connected with Cassandra through Cassandra’s mother, leading to a dynamic synergy that benefits every student and horse under their care. This combination of expertise allows the team to rehabilitate challenging horses, guide beginners through their first lessons, and coach athletes striving for national finals. It is this foundation that ensures our training is both technically sound and results-driven, setting a new standard for professional equestrian programs in Pleasanton and the greater East Bay.

Each member of our team shares a commitment to technical instruction, goal-oriented progression, and a welcoming atmosphere. We believe in teaching the 'why' behind every rider aid, meeting the needs of analytical adult learners and ambitious youth alike. Our trainers prioritize clear communication and safety, using biomechanical horse matching to pair horses and riders for the best possible results. The team’s experience extends to fixing behavioral issues in performance horses and guiding students to overcome challenges, from building confidence in shy beginners to preparing seasoned riders for regional and national finals. Parents trust us for our structured approach, while competitive athletes choose us for our proven track record. Our trainers are more than instructors. They are mentors and partners in each rider’s journey.

Read More About Cassandra
About Cassandra

Cassandra Keith began her riding career at the age of 2 and was competing by the age of 4. Born and raised in the Mid-West, her family ran and operated a Welsh breeding program. The program also managed imports, trained and competed in Dressage and 3-day eventing, boasted a large lesson program, rescued large and small animals and ran a program for the disabled and troubled youth.

Cassandra is the daughter of a professional South African Grand Prix Dressage and Hunt Seat rider. The opportunities presented to her were abundant. She rode with Canadian Eventing 2* rider Derek O’Connor, Australian Grand Prix rider Wesley Singleton, European Grand Prix rider and owner of Equi-Globe Sales International Imports Hartmut Gutzmann and US Grand Prix rider and R Judge Julie Winkel. She attended clinics with George Morris and Denny Emerson, to name just a few. At the age of 8, Cassandra was the youngest to receive certification with CHA and then receiving her Assistant Trainer Certification at age 16. She studied the British Horse Society System and the American Forward Riding System. She participated in Pony Club to B level and joined IEA and in her last year of high school. Her development focused on riding and competing in Dressage and Jumpers, showing successfully at the 1.20m by the age of 15.

By the time she was 16, she had many years of experience in various training and teaching methods. Cassandra was homeschooled so she could focus on her riding, in order to build a career in the industry. Training and working with many young horses in preparation for their sale, she developed an understanding of how to develop quality horses. She trained multi- disciplined ponies, warmbloods, arabs, and mustangs.

Her passion and comprehensive understanding of the horse’s mechanics and conformation has given her the ability to develop horses to their full potential and help her students learn to do the same. Moving out to the West Coast at age 15, she spent a year as an intern with Julie Winkel, where she received in-depth training in the industry from a seasoned professional. When she moved to the Bay Area in 2007, she worked in many training and lesson programs before starting her own business in 2011.

Read More About Leah
About Leah

Leah Feliz grew up in Palo Alto, California and has had horses in her life since she was just a couple of years old. She and her sister spent most of their free time in the foothills, riding from dawn to dusk and even camping out with their horses in forts they built in the woods.

When Leah went off the college, she had to sell her childhood horse Blaze, but she never forgot the passion and love she felt for her horse. While getting her Bachelor of Science at UC San Diego, she found ways to ride and continued riding throughout her life. When she had her own children, her youngest son developed his own passion for horses working for the Square Peg Foundation, a therapeutic riding program in Half Moon Bay. There, Leah rediscovered her love for horses and working with children. She quickly bought her son a beautiful Thoroughbred mare named Pearl, who was from New Zealand and had come to the United States to run on the track. Square Peg had rescued Pearl and she joined Leah’s family. Leah and Pearl spent several years racing in the sport of endurance. During that time Leah also purchased an anglo-arab mare named Halle and it was with Halle that Leah grew in her knowledge of Horsemanship. With the help of Chris Ellsworth and his horsemanship clinics, Leah learned more about herself from Halle than from any other experience. Halle taught her how to communicate with horses and how to give them the best life possible. Sadly, Leah lost Pearl to an injury in 2013 and the loss was so great that she wasn’t sure if she would ever find a way to heal. During that time she met Cassandra Keith and their friendship would lead Leah not only to purchase many more horses, but to leave her full-time career to partner with Cassandra teaching and training in the hunter-jumper sport.

Leah has also participated in multiple clinics with Julie Winkel, received certification in Carla Bauchmueller’s Centered Riding Master Class Program and continues to train in the hunter-jumper sport. Her extensive knowledge and experience in horsemanship, equine nutrition and wound care have given Leah the opportunity to work with many horses and successfully maintain their health and wellbeing. She hopes to spend the rest of her life helping more children build confidence and motivation through a bond with a horse, as well as dedicating her time to caring for the horses in her life to ensure they live in the best conditions possible.

Leah feels strongly that Five Star Equestrian has a philosophy that lends itself to building confidence in its clients and horses and that, along with Cassandra’s extensive knowledge in the hunter-jumper sport, their program will provide a place for young riders to thrive. Leah rides and shows in hunter-jumpers and you will find her at the barn or in a pasture with her horses just about any day.