Pipster Prep Staff

Tessa Steinberg

Tessa Steinberg is the Director and Owner of Pipster Prep. Tessa earned her Bachelor’s Degree in Business Accounting from Oregon State University. After working in the accounting field for a few years, she decided to make a career change. With a love of children and education, Tessa moved to South Korea where she taught English to children ages three to ten years old. Upon returning to Portland, she enrolled at University of Portland and earned her Master’s in Teaching. She went on to teach Kindergarten and First Grade in the Evergreen School District. As a kindergarten and first grade teacher, she saw how important kindergarten readiness was. Her dream of opening a preschool began while in Korea, and with her experience in public education, she is excited to be able to prepare students for entering elementary school.

Jessica Castrapel
SW Site Director

Jessica Castrapel is the Pipster Prep Southwest Site Director. Jessica started at Pipster Prep in September 2014. She has 14 years of experience as a nanny. She earned a Bachelor of Science in Psychology from Portland State University and a Master of Education from Loyola University. Jessica is Montessori trained and earned an Assistance to Infancy Teaching Diploma from Montessori Institute Northwest. Jessica has a passion for early education and knows that providing an environment full of rich, happy experiences aids a child in developing a love for learning. Her goal is to inspire children to seek peace, reveal their uniqueness, and fulfill their potentials. She enjoys gardening, paddle boarding, and spending time with her dogs, chickens, and husband, Elias.

Briar Hayworth
NW Site Director

Briar Hayworth is the Site Director of Pipster Prep Northwest. Briar started working at Pipster Prep as an Assistant Teacher when it opened in April 2014. She earned her Bachelors in Child and Family Studies with a focus on Early Childhood Education at Portland State University and is currently working towards her Masters in Education. Briar is passionate about early education and inspiring children to love learning. She believes that building community in the classroom is the foundation for a creative and exciting learning experience. In her free time, she enjoys reading, watching old films, and baking.

Alisha Harms
NW Teacher

Alisha Harms is the Head Teacher in our Rabbit Classroom. Alisha started at Pipster Prep in September of 2017. She received her bachelor’s degree from Earlham College in Richmond, Indiana with a major in Biology. After college, Alisha moved to Portland and worked as a nanny for five years. She also spent a year interning at OMSI in their Early Childhood Education Department before starting at Pipster Prep. Alisha has always loved working with children, and believes that providing a space that caters to everyone's individuality will instill a love for learning throughout their entire life. In her spare time, Alisha loves hiking, birding, and crafting.

Laura Gwin
NE Site Director, Teacher

Laura Gwin is the Pipster Prep Northeast Site Director and Head Teacher in our NE Fawn Classroom. Laura earned a bachelor’s degree in Communications from the University of San Diego. After working in Interior Design, Laura made a career change. She spent the past two years as a Lead Teacher at a preschool in San Francisco. She has a true love of learning and a passion for working with young children. She has since completed additional coursework in Early Childhood Education. Laura has a natural ability to care for, understand and connect with children. She believes that confidence and self-awareness can be achieved amongst students by regular positive reinforcement, which Laura instills in her teaching method daily. She is an abstract artist and also enjoys singing, baking, hiking, crafting, and trying new restaurants.

Breanna Briggs
NE Teacher

Breanna Briggs is the Head Teacher in our Bear Classroom. Breanna started at Pipster Prep in February of 2016 before finishing her bachelor’s degree in Environmental Science at Portland State University. She spent her time before Pipster Prep living in Belgium, traveling to study French and nannying in Southern California. Breanna is passionate about providing students with a communal space to be creative, inquisitive and kind and believes fostering those skills will help instill an early love of learning that will continue throughout their lifetimes. When Breanna is not teaching, she enjoys hiking, spending time in her garden, cooking and playing with her dog, Frannie.

Hannah Maculsay
NE Teacher

Hannah Maculsay is the Head Teacher in our Raccoon Classroom. Hannah started at Pipster Prep in October of 2017. She earned her bachelor’s degree in communications from Portland State University. Her desire for teaching is to provide an enthusiastic and positive experience for children just beginning their education path. Hannah aims to instill kindness in the classroom and create a harmonious environment for children to grow. Hannah is passionate about exploring the world and she spends her time going to concerts, making DIY aromatherapy and has a special place in her heart for the beach.

Rachel Podrabsky
NW Teacher

Rachel Podrabsky is the Head Teacher in our NW Raccoon Classroom. Rachel started at Pipster Prep in October 2018. She earned a bachelor's degree in Psychology from the University of Oregon in 2015. Before beginning her career at Pipster Prep, Rachel worked for the David Douglas School District as an Instructional Assistant for 3 years. Rachel is most interested in helping students become successful by working with each individual student's personal needs. She hopes to build a child's independence by teaching the social and emotional skills that are so needed when heading into their early childhood and beyond. Rachel enjoys spending time with friends, traveling, camping, and reading.

Anna Breswick
SW Teacher

Anna Breswick is the Head Teacher in our SW Fox Classroom. Anna grew up in a family of teachers, so it was no surprise when she moved to Oregon to pursue a Master of Arts in Teaching from Oregon State University in 2005. She spent the next ten years teaching Spanish and working in preschools in the summer months back in her home state of Colorado. After staying home with her daughter for a few years, she took a job as a teacher assistant in the Kindergarten Classrooms at Bridlemile Elementary. That experience reignited her spark for early childhood education. She is very excited to be teaching Pre-K at Pipster Prep, where she hopes to incorporate her love for language development, literacy, music, and nature into her class. In her free time she enjoys exploring the outdoors with her family.

Kelly Schilling
NW Teacher

Kelly Schilling is a Head Teacher in our NW Fawn Classroom. Kelly started at Pipster Prep as an Assistant Teacher in February of 2018. She was born and raised in the greater Portland area. Kelly earned her Bachelor’s Degree in Sociology with a focus on children and families from Oregon State University. Kelly has always wanted to work with children and has prior experience as a nanny for a family of three girls. She is excited to have the opportunity to be a daily part of childrens’ preliminary education experiences. It is her purpose to make each day a great day for every child, and to help them develop and get ready not only for kindergarten but for life.

Morgan Lethin
NW Teacher

Morgan Lethin is the Head Teacher in our NW Owl Classroom. Morgan started at Pipster Prep in December of 2018 as an assistant while finishing up her degree at Portland State University in Social Sciences with a minor in Child and Family studies. Morgan is passionate about early childhood education and believes in fostering an environment that is rich in communication, love and kindness. Morgan has always loved working with children and finds it valuable to balance structure with carefree spontaneity. When Morgan is not at Pipster Prep, she enjoys spending time outdoors with her family, baking and reading a good book.

Amina Diakite
SW Teacher

Amina Diakite is the Head Teacher in our SW Rabbit Classroom. Amina started as an Assistant Teacher at Pipster Prep in April 2018. She earned her bachelor's degree in Liberal Studies with a minor in Sociology from Portland State University. Growing up she spent time helping at her father’s tutoring center in Mali, West Africa. Amina grew up attending schools in Portland that promoted the arts, and developed a passion for dance. She began teaching dance classes and gymnastics to children and found she loved being a part of their growth and development. After college Amina worked as a Behavioral Therapist for children with Autism. At Pipster Prep she aims to guide and nurture children, preparing them for school and helping them build self confidence. Amina values the idea that teaching is a give and take process, and that it is important to listen to children as we can learn from them as well.

Christa Baker
SW Teacher

Christa Baker is the Head Teacher in our SW Fawn Classroom. Christa has a Bachelor’s degree in Early Childhood Education and has worked with kids for more than 28 years. She moved to Portland from Springfield, Illinois five years ago, and loves it. She is a mother of six children from 24 to seven years old. Teaching and spending time with children is a true passion of hers. As a preschool teacher her goal is to foster independence. This allows them to become more confident in themselves and creates a sense of self worth and achievement. She works with each student so they learn self control, strong coping skills, and skills for good social interactions. Above all, she wants her students to feel safe, loved, and valued.

Nina Kessler
NW Teacher

Nina Kessler is the Head Teacher in our NW Fox Classroom. Nina earned a Bachelors of Science in Social Science from Portland State University and plans on pursuing her masters degree in teaching. She has been a nanny for nearly ten years and has traveled the world, spending time in schools from Cambodia to Belize. She believes strongly in fostering a love for learning early on by nurturing children’s curiosity through play. When Nina isn’t teaching she enjoys exploring the Portland food scene, listening to podcasts, traveling with friends, and watching true crime.