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
Hillside Site Director, Teacher

Alisha Harms is the Hillside Site Director and 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
NW Teacher

Laura Gwin is the Head Teacher in our NW Owl 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.

Hannah Maculsay
NE Site Director, Teacher

Hannah Maculsay is the NE Site Director and 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.

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.

Amina Diakite
Hillside Teacher

Amina Diakite is the Head Teacher in our Hillside Fawn 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.

Jeske Paanakker
SW Teacher

Jeske Paanakker is the Head Teacher in our SW Bear Classroom. Jeske started at Pipster Prep in June 2019 as an assistant teacher while finishing up her degree in Human Development and Family Sciences and specializing in Child Development and Early Education at Oregon State University. Before beginning her career at Pipster Prep, Jeske has gained valuable experiences from working at an Early Intervention Preschool, a Head Start Preschool, and a variety of drop-off daycares. She understands the importance of developing social and emotional skills in young students in order to foster independence and set them up for success for life after preschool. Jeske has always been passionate about working with children, and aims to fill her classroom with as much positivity, creativity, and individuality as possible.

Taylor Simonds
SW Teacher

Taylor Simonds is the Head Teacher in our SW Owl Classroom. Taylor started as an Assistant Teacher at Pipster Prep in August 2019 while she finished up her degrees in Psychology and Liberal Studies at Portland State University. Taylor has always had a passion for working with kids. She has been a nanny for the past 4 years; taking summers off to spend time abroad teaching art-based therapy to children living in refugee camps. She believes the classroom should be a place that above all hosts kindness and nurtures each student’s individuality and creativity. When Taylor isn’t at Pipster Prep, she enjoys spending time with her puppy, camping, hiking, and reading a good book.

Maddie Cois
SW Teacher

Maddie Cois is the Head Teacher in our SW Fox Classroom. Maddie started at Pipster Prep in September 2019 as an assistant teacher. She earned a Bachelor’s degree in Education from University of Oregon and then studied abroad in Australia where she was able to gain more experience in classrooms around the world. Maddie came home and attended University of Portland earning a Master of Teaching. This opened many doors for Maddie and she ended up moving back to Australia, working in a university while completing a Master of Counseling and she also met her husband. Since then, Maddie has continued her passion for teaching by working with students ages two through adult. Maddie’s main goal is to celebrate each student’s unique gifts and always foster their innate curiosity and love of learning. Maddie loves playing board games, traveling and reading books with her two sons (who also attend Pipster Prep).

Macy Ferrer
NW Teacher

Macy Ferrer is the Head Teacher is our NW Bear Classroom. She received her Montessori Teaching credential in Early Childhood from the Montessori Training and Education Center. Before working at Pipster Prep, Macy was teaching at a Montessori School for three years in the Bay Area. She has always been very passionate about working with children, especially young ones. Macy enjoys watching students grow and learn from each other. She believes that each child has something unique to offer, and a good way for them to express that is in the classroom environment. In her spare time, she enjoys spending time with her boyfriend, Charlie and taking in all of Portland’s amazing little food spots and beauty!

Megan Maculsay
NE Teacher

Megan Maculsay is the Head Teacher in our NE Bear Classroom. Megan started at Pipster Prep in January 2020. She began her career in the field of psychology and child development in 2015 working as a Behavior Therapist to children with Autism Spectrum Disorder. She completed her Bachelor’s of Arts Degree in Psychology at California State University San Marcos in 2017, and continued her work in behavior therapy in Portland, Oregon. With over four years of experience working with children with ASD, she has gained an even more comprehensive understanding of the developing mind, as well as how to effectively support families. Megan believes in creating an accepting classroom environment, helping each student explore what it means to be a kind and compassionate individual. Creative problem solving, positive reinforcement, and fostering critical thinking skills are some of the core values that Megan promotes in her classroom. Outside of the classroom, Megan enjoys drawing, cooking for loved ones, and venturing out to the forest or coast whenever possible.

Madison Swindler
SW Teacher

Madison Swindler is the Head Teacher in our SW Raccoon Classroom. Madison has been a Co-Teacher at SW Pipster Prep since October 2020. Madison earned her Bachelor’s degree in Urban Planning and Sustainable Development at Western Washington University. Before her career at Pipster, Madison was affiliated with an organization called Common Threads; which connects children to nutritional, sustainable food through cooking and gardening classes. Madison is a compassionate and empathetic person which translates into her love for the kids she works with. Her goal is to create a classroom environment that best highlights each student's individuality. When Madison is not at Pipster Prep, she enjoys camping, cooking, painting, and being surrounded by her loved ones.

Mariah Cornett
SW Teacher

Mariah Cornett is the Head Teacher in our SW Rabbit Classroom. Mariah earned her Bachelor's degree in Psychology with minors in both Human Development and Human Resources from Washington State University. Before working at Pipster Prep, Mariah worked in the mental health field; focusing on children with developmental disabilities. Mariah is patient, caring, and loves to make learning fun! She believes it is important to create a learning environment based on mutual trust and open communication. Mariah aims to make sure that each student always feels heard and treated fairly. It is her goal to help her students develop the skills needed to become independent and resilient individuals.

Caroline Baker
SW Teacher

Caroline Baker is the Head Teacher in our SW Fawn Classroom. She earned her Bachelor’s degree in English from the University of Oregon. Caroline brings to the classroom a passion for early childhood learning and literacy. Prior to Pipster Prep, she worked for a tutoring firm assisting students with test preparation and subject support. Caroline strives to build a classroom of strong community through teaching communication and courtesy, and to foster imagination and independence in her students. She desires to provide her students with a loving environment that promotes kindness while building self esteem and social skills. When not at Pipster Prep, Caroline loves to go for long runs, spend time with her husband and family, explore the outdoors, and curl up with a good book and her cats.

Lindsey Jamerson
NW Teacher

Lindsey Jamerson is the Head Teacher in our NW Rabbit Classroom. Lindsey started as a Co-Teacher in the NE PreK Classroom in May 2020. She worked as a nanny for over six years while she obtained her Bachelor of Science degree in Urban & Public Affairs from Portland State University. She strives to incorporate what she learned throughout her schooling about inclusivity, community development and environmentalism into her classroom. She hopes to do this by building strong social-emotional skills as well as creating a deep sense of community and empathy for others. She believes that ensuring students learn these values at a young age is the key to a brighter future for us all. When Lindsey is not teaching she enjoys traveling, seeing live music, cooking, spending time with friends and family, and caring for her four chickens and her dog.