Cover image of show Pencils Down with Jamie Williamson

Pencils Down with Jamie Williamson

Podcast by The Windward School

English

Technology & science

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About Pencils Down with Jamie Williamson

Welcome to Pencils Down with Jamie Williamson. In each episode, Jamie will engage in informal, unscripted conversations with key community members—to learn more about their professional journey, the work they do for Windward, and the impact they have within our community. Guests will dive into a variety of topics including school life, curriculum, dyslexia, and other important issues that impact our students, faculty, staff, and community. Join us each month to hear our guests' inspiring stories and learn from the incredible individuals who help make a difference in the lives of our students.

All episodes

15 episodes

episode Pencils Down With Jamie Williamson Episode 15: Daniele Kass, EdD, Campus Head of Westchester Lower School artwork

Pencils Down With Jamie Williamson Episode 15: Daniele Kass, EdD, Campus Head of Westchester Lower School

In this episode, Jamie Williamson is joined by Westchester Lower School’s Campus Head Dr. Daniele Kass. Dr. Kass shares her experience as the mother of a dyslexic child and reflects on the importance of support among family. They exchange stories of mentorship and their core values, and discuss the strength of Windward’s RULER program for both students and faculty. The Windward School Official Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/] Windward is a coeducational, independent day school dedicated to providing a proven instructional program for children with language-based learning disabilities. The multisensory curriculum is designed for students of average to superior intelligence who can benefit from the unique educational experience provided. Through direct instruction in small class settings, a trained staff assists students to improve their language skills. Academic success, combined with opportunities for social and emotional growth within an intentionally diverse and inclusive setting, enables students to understand their learning differences, build confidence, and develop self-advocacy skills. Windward is committed to helping students achieve their full potential in preparation for a successful return to a mainstream educational environment. To meet these goals, the School provides ongoing training to its faculty based on the most current research and shares its expertise with the parent body, other educators, and the broader community. Our Vision: A world where every child with a language-based learning disability is empowered to achieve unlimited success. Our Core Values Commitment – Windward maintains a disciplined and rigorous approach to all we do, and our every action is guided by an unparalleled commitment to a world where every child with a language-based learning disability is empowered to achieve unlimited success. Growth – We believe that everyone is capable of growing and learning. At Windward, a growth mindset is shared by all and takes many forms, from academic growth for students to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠professional growth⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/about/teacher-training-program] for faculty and staff. Impact - Each day Windward strives to serve as many students as we can and to make a life-changing and transformational impact on every individual child in the classroom as well as within the ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠greater learning disability population⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/fs/pages/247]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/the-windward-institute] Community - Windward believes in fostering a strong, cohesive, and collaborative culture and building a ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠diverse and inclusive community⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/about/deib] that puts our students at the center of all we do, and where everyone feels valued and a sense of belonging. At The Windward School, we are committed to a world where every child with a language-based learning disability is empowered to achieve unlimited success – a vision fulfilled by disrupting the educational status quo. The Windward School deliberately builds both its curriculum and culture to foster a powerful sense of belonging through a research-based program that is authentically inclusive and a community in which everyone is seen in their full humanity.  The Windward School aspires to bring forth students who are culturally engaged critical thinkers, confident self-advocates who understand and celebrate their differences, and upstanders who identify and challenge all forms of injustice. Windward is committed to these values and expectations of its community members by embracing the importance of ongoing anti-oppression dialogue and critical conversations; by advancing educational equity in underrepresented communities, especially those historically marginalized by society; and by working to ensure that our program is accessible to all who need it.

1 May 2026 - 33 min
episode Pencils Down With Jamie Williamson Ep 14: Kara Schremser, Teacher Training Program Director artwork

Pencils Down With Jamie Williamson Ep 14: Kara Schremser, Teacher Training Program Director

In this episode, Jamie Williamson is joined by Windward's Teacher Training Program Director Kara Schremser. Kara offers an inside look at the depth and intentionality behind Windward’s Teacher Training Program and how it shapes our teachers. They discuss the importance of the program and Kara's journey - from first arriving at Windward as a teacher to where she is now! ⁠⁠⁠The Windward School Official Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/] Windward is a coeducational, independent day school dedicated to providing a proven instructional program for children with language-based learning disabilities. The multisensory curriculum is designed for students of average to superior intelligence who can benefit from the unique educational experience provided. Through direct instruction in small class settings, a trained staff assists students to improve their language skills. Academic success, combined with opportunities for social and emotional growth within an intentionally diverse and inclusive setting, enables students to understand their learning differences, build confidence, and develop self-advocacy skills. Windward is committed to helping students achieve their full potential in preparation for a successful return to a mainstream educational environment. To meet these goals, the School provides ongoing training to its faculty based on the most current research and shares its expertise with the parent body, other educators, and the broader community. Our Vision: A world where every child with a language-based learning disability is empowered to achieve unlimited success. Our Core Values Commitment – Windward maintains a disciplined and rigorous approach to all we do, and our every action is guided by an unparalleled commitment to a world where every child with a language-based learning disability is empowered to achieve unlimited success. Growth – We believe that everyone is capable of growing and learning. At Windward, a growth mindset is shared by all and takes many forms, from academic growth for students to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠professional growth⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/about/teacher-training-program] for faculty and staff. Impact - Each day Windward strives to serve as many students as we can and to make a life-changing and transformational impact on every individual child in the classroom as well as within the ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠greater learning disability population⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/fs/pages/247]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/the-windward-institute] Community - Windward believes in fostering a strong, cohesive, and collaborative culture and building a ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠diverse and inclusive community⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/about/deib] that puts our students at the center of all we do, and where everyone feels valued and a sense of belonging. At The Windward School, we are committed to a world where every child with a language-based learning disability is empowered to achieve unlimited success – a vision fulfilled by disrupting the educational status quo. The Windward School deliberately builds both its curriculum and culture to foster a powerful sense of belonging through a research-based program that is authentically inclusive and a community in which everyone is seen in their full humanity.  The Windward School aspires to bring forth students who are culturally engaged critical thinkers, confident self-advocates who understand and celebrate their differences, and upstanders who identify and challenge all forms of injustice. Windward is committed to these values and expectations of its community members by embracing the importance of ongoing anti-oppression dialogue and critical conversations; by advancing educational equity in underrepresented communities, especially those historically marginalized by society; and by working to ensure that our program is accessible to all who need it.

18 Feb 2026 - 33 min
episode Pencils Down With Jamie Williamson Ep 13: Melissa Stewart, Associate Director of Development artwork

Pencils Down With Jamie Williamson Ep 13: Melissa Stewart, Associate Director of Development

In this episode, Head of School Jamie Williamson is joined by Melissa Stewart, associate director of development who talks about how her lifelong travels have impacted her approach to her work, the value of empathy and optimism, and the importance of connecting with families to advance the mission of The Windward School. ⁠⁠⁠The Windward School Official Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/] Windward is a coeducational, independent day school dedicated to providing a proven instructional program for children with language-based learning disabilities. The multisensory curriculum is designed for students of average to superior intelligence who can benefit from the unique educational experience provided. Through direct instruction in small class settings, a trained staff assists students to improve their language skills. Academic success, combined with opportunities for social and emotional growth within an intentionally diverse and inclusive setting, enables students to understand their learning differences, build confidence, and develop self-advocacy skills. Windward is committed to helping students achieve their full potential in preparation for a successful return to a mainstream educational environment. To meet these goals, the School provides ongoing training to its faculty based on the most current research and shares its expertise with the parent body, other educators, and the broader community. Our Vision: A world where every child with a language-based learning disability is empowered to achieve unlimited success. Our Core Values Commitment – Windward maintains a disciplined and rigorous approach to all we do, and our every action is guided by an unparalleled commitment to a world where every child with a language-based learning disability is empowered to achieve unlimited success. Growth – We believe that everyone is capable of growing and learning. At Windward, a growth mindset is shared by all and takes many forms, from academic growth for students to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠professional growth⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/about/teacher-training-program] for faculty and staff. Impact - Each day Windward strives to serve as many students as we can and to make a life-changing and transformational impact on every individual child in the classroom as well as within the ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠greater learning disability population⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/fs/pages/247]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/the-windward-institute] Community - Windward believes in fostering a strong, cohesive, and collaborative culture and building a ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠diverse and inclusive community⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/about/deib] that puts our students at the center of all we do, and where everyone feels valued and a sense of belonging. At The Windward School, we are committed to a world where every child with a language-based learning disability is empowered to achieve unlimited success – a vision fulfilled by disrupting the educational status quo. The Windward School deliberately builds both its curriculum and culture to foster a powerful sense of belonging through a research-based program that is authentically inclusive and a community in which everyone is seen in their full humanity.  The Windward School aspires to bring forth students who are culturally engaged critical thinkers, confident self-advocates who understand and celebrate their differences, and upstanders who identify and challenge all forms of injustice. Windward is committed to these values and expectations of its community members by embracing the importance of ongoing anti-oppression dialogue and critical conversations; by advancing educational equity in underrepresented communities, especially those historically marginalized by society; and by working to ensure that our program is accessible to all who need it.

2 Dec 2025 - 28 min
episode Pencils Down With Jamie Williamson Ep 12: Diane Kissner, Outplacement Director artwork

Pencils Down With Jamie Williamson Ep 12: Diane Kissner, Outplacement Director

Jamie is joined by Outplacement Director Diane Kissner. Diane reflects on her 30 years at Windward, the work of the outplacement department, and the relationships she has built with families over the years. They also dive into Windward's grade 8 study skills program and how it helps students prepare for the transition to high school. ⁠⁠The Windward School Official Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/] Windward is a coeducational, independent day school dedicated to providing a proven instructional program for children with language-based learning disabilities. The multisensory curriculum is designed for students of average to superior intelligence who can benefit from the unique educational experience provided. Through direct instruction in small class settings, a trained staff assists students to improve their language skills. Academic success, combined with opportunities for social and emotional growth within an intentionally diverse and inclusive setting, enables students to understand their learning differences, build confidence, and develop self-advocacy skills. Windward is committed to helping students achieve their full potential in preparation for a successful return to a mainstream educational environment. To meet these goals, the School provides ongoing training to its faculty based on the most current research and shares its expertise with the parent body, other educators, and the broader community. Our Vision: A world where every child with a language-based learning disability is empowered to achieve unlimited success. Our Core Values Commitment – Windward maintains a disciplined and rigorous approach to all we do, and our every action is guided by an unparalleled commitment to a world where every child with a language-based learning disability is empowered to achieve unlimited success. Growth – We believe that everyone is capable of growing and learning. At Windward, a growth mindset is shared by all and takes many forms, from academic growth for students to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠professional growth⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/about/teacher-training-program] for faculty and staff. Impact - Each day Windward strives to serve as many students as we can and to make a life-changing and transformational impact on every individual child in the classroom as well as within the ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠greater learning disability population⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/fs/pages/247]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/the-windward-institute] Community - Windward believes in fostering a strong, cohesive, and collaborative culture and building a ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠diverse and inclusive community⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/about/deib] that puts our students at the center of all we do, and where everyone feels valued and a sense of belonging. At The Windward School, we are committed to a world where every child with a language-based learning disability is empowered to achieve unlimited success – a vision fulfilled by disrupting the educational status quo. The Windward School deliberately builds both its curriculum and culture to foster a powerful sense of belonging through a research-based program that is authentically inclusive and a community in which everyone is seen in their full humanity.  The Windward School aspires to bring forth students who are culturally engaged critical thinkers, confident self-advocates who understand and celebrate their differences, and upstanders who identify and challenge all forms of injustice. Windward is committed to these values and expectations of its community members by embracing the importance of ongoing anti-oppression dialogue and critical conversations; by advancing educational equity in underrepresented communities, especially those historically marginalized by society; and by working to ensure that our program is accessible to all who need it.

10 Nov 2025 - 26 min
episode Pencils Down With Jamie Williamson Ep 11: JP Bifone, Director of Marketing and Communications artwork

Pencils Down With Jamie Williamson Ep 11: JP Bifone, Director of Marketing and Communications

In this episode of Pencils Down, Jamie is joined by Windward's Director of Marketing and Communications JP Bifone to discuss the work of the marketing and communications department and how the team helps to get Windward's message out there. They dive into some of the work of the department including the recent launch of a new website for the School and JP's journey to Windward. ⁠⁠The Windward School Official Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/] Windward is a coeducational, independent day school dedicated to providing a proven instructional program for children with language-based learning disabilities. The multisensory curriculum is designed for students of average to superior intelligence who can benefit from the unique educational experience provided. Through direct instruction in small class settings, a trained staff assists students to improve their language skills. Academic success, combined with opportunities for social and emotional growth within an intentionally diverse and inclusive setting, enables students to understand their learning differences, build confidence, and develop self-advocacy skills. Windward is committed to helping students achieve their full potential in preparation for a successful return to a mainstream educational environment. To meet these goals, the School provides ongoing training to its faculty based on the most current research and shares its expertise with the parent body, other educators, and the broader community. Our Vision: A world where every child with a language-based learning disability is empowered to achieve unlimited success. Our Core Values Commitment – Windward maintains a disciplined and rigorous approach to all we do, and our every action is guided by an unparalleled commitment to a world where every child with a language-based learning disability is empowered to achieve unlimited success. Growth – We believe that everyone is capable of growing and learning. At Windward, a growth mindset is shared by all and takes many forms, from academic growth for students to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠professional growth⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/about/teacher-training-program] for faculty and staff. Impact - Each day Windward strives to serve as many students as we can and to make a life-changing and transformational impact on every individual child in the classroom as well as within the ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠greater learning disability population⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/fs/pages/247]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/the-windward-institute] Community - Windward believes in fostering a strong, cohesive, and collaborative culture and building a ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠diverse and inclusive community⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.thewindwardschool.org/about/deib] that puts our students at the center of all we do, and where everyone feels valued and a sense of belonging. At The Windward School, we are committed to a world where every child with a language-based learning disability is empowered to achieve unlimited success – a vision fulfilled by disrupting the educational status quo. The Windward School deliberately builds both its curriculum and culture to foster a powerful sense of belonging through a research-based program that is authentically inclusive and a community in which everyone is seen in their full humanity.  The Windward School aspires to bring forth students who are culturally engaged critical thinkers, confident self-advocates who understand and celebrate their differences, and upstanders who identify and challenge all forms of injustice. Windward is committed to these values and expectations of its community members by embracing the importance of ongoing anti-oppression dialogue and critical conversations; by advancing educational equity in underrepresented communities, especially those historically marginalized by society; and by working to ensure that our program is accessible to all who need it.

26 Oct 2025 - 34 min
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