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Caileigh Bryant has worked in a variety of roles within the equine and education industries since 2012. Caileigh began their career as an Equestrian Trainer at Gravity Hill Farm in 2012, followed by a Riding Instructor position at Meadowbrook Stables in 2016. In 2013, they also took on a Sales Associate role at Folly. From 2017-2021, Caileigh worked as an English Language Arts Teacher at UniversityTutor, providing private duty tutoring services for middle and high school students. During this time, they also worked as an Equine Sports Massage Therapist at Resilience Equine and an Equestrian Program Director at Girl Scouts of the Green and White Mountains. In 2021, they began their current role as a Pre Kindergarten Teacher at The Croft School and a Stable Manager at The Stable on the Woods. Most recently, in 2022, Caileigh began working as a Lead Pre-K Teacher at SolBe Learning.

Caileigh Bryant attended Thetford Academy from 2004 to 2010, earning their High School degree. Caileigh then attended Sweet Briar College from 2011 to 2014, earning a Bachelor's Degree in English and Creative Writing. Finally, they attended the University of Massachusetts Amherst from 2017 to 2019, studying Elementary Education and Teaching.