Mission
Pollyanna Builds Stronger and Kinder Communities.
We do this by equipping people and institutions with the tools, knowledge, and courage to live their values with greater clarity, consistency, and care. We believe kindness, connection, and inclusion are not extras. They are essential to the health, strength, and future of every thriving school, organization, and community.
Our Strategy
Pollyanna partners with academic institutions, nonprofits, and corporations to help turn values into action.
Through our signature conference models, interactive workshops, community assessments, leadership development, and original curricula, we help communities strengthen trust, deepen understanding, and navigate complexity with greater confidence and purpose.
Our work is designed to move beyond aspiration. We create opportunities for reflection, honest dialogue, skill-building, and action so that every member of a community has a role in shaping a culture where people feel seen, valued, and responsible for one another.
We believe lasting change happens when communities are given both the space to reflect and the tools to move forward together.
What We Believe: At Pollyanna, our work is grounded in a few core beliefs:
Strong communities are built, not assumed: Healthy communities do not happen automatically. They require intention, care, reflection, and a willingness to grow.
Every member of a community has a role to play: Students, educators, leaders, staff, trustees, parents/caregivers, and community partners all shape culture. Lasting change happens when communities learn and lead together.
Kindness and courage belong together: Kindness is not passive. It asks us to listen, reflect, speak honestly, and act with integrity, even when the work is difficult.
Reflection must lead to action: Awareness matters, but awareness alone is not enough. Communities grow stronger when insight is paired with practical steps forward.
Building community is ongoing work: There is no finish line. Stronger and kinder communities are built over time, through repeated choices, shared responsibility, and sustained commitment.
Why This Work Matters Now
Schools, organizations, and communities are navigating a time of extraordinary complexity.
Across the country, many people are feeling more disconnected, more cautious, and less certain about how to engage across difference. Institutions are being asked to lead through polarization, pressure, and change while still remaining grounded in their values.
This moment calls for more than statements or surface-level solutions. It calls for spaces where people can reflect honestly, build trust, strengthen communication, and practice the skills needed to live and lead in community.
That is where Pollyanna comes in.
We help communities move from intention to action and from uncertainty to greater clarity, connection, and purpose.
All in service of Building Stronger and Kinder Communities.
Pollyanna Team
At Pollyanna, our work is carried forward by a deeply committed team of educators, facilitators, and leaders who believe in the power of community and the responsibility we all share in shaping it.
Our team brings together a breadth of experience across schools, nonprofits, and organizations, along with a shared dedication to thoughtful engagement, meaningful dialogue, and lasting impact. We approach this work with both care and rigor, supporting communities as they navigate complexity, strengthen relationships, and align their actions with their values.
What unites us is a belief that this work matters, and that it is possible. We are honored to partner with communities across the country and to contribute, in ways both big and small, to Building Stronger and Kinder Communities.
Casper Caldarola
Pollyanna Founder
Casper Caldarola founded the New York based, non-profit, Pollyanna in 2015. Casper has worn many hats in independent schools: alum, parent, administrator, and trustee, and saw different levels of commitment to DEI work. She felt and still feels the most important aspect of this work is to keep the academic, social, and emotional needs of the student at the center. Casper founded Pollyanna to support the schools that have made a commitment to building a more inclusive school community through multi-constituent conference models, workshops, community assessments and racial literacy curriculum.
Casper’s experience includes serving as president of the Dalton School Parents Association. During her tenure, she created a more inclusive community, developed a new budgeting structure making it possible for parents of different socioeconomics to volunteer, hosted more events at school to take the pressure off of in-home hosting, and introduced monthly topic-driven parent discussions to find additional ways to bring the community together. In addition, Casper was the Communications Director at the Allen-Stevenson School and was tasked with helping to develop and implement equity initiatives, such as, developing a more inclusive hiring process and creating Parent Chats with topics that focused on DEI. Before joining the independent school world, she was a marketing and advertising executive.
Casper now serves on the Board of Seeds of Peace. She was a trustee at the Dalton School for 10 years and served as a member of the Executive Committee, chaired the Committee on New Trustees and Community Life & Diversity Committee, and was on the strategic plan steering committee, and has also served on the boards of Parents-in-Action and Generation Citizen.
Dayna Campbell
Pollyanna Chief of Staff
Dayna Campbell is a systems-minded operations leader who partners closely with Pollyanna’s Founder to align strategy, internal operations, and cross-functional initiatives. She brings over a decade of experience in higher education, nonprofit management, and dialogue facilitation, with expertise in strategic planning, program design, and equity-centered team development.
A former volunteer and (current) Advisor to the Pollyanna Teen Council, Dayna’s work is grounded in intergenerational leadership and the belief that operational excellence and inclusive practices are essential to sustainable change. She is pursuing a master’s in Organizational Development and Leadership and holds a B.A. with honors in Educational Studies from Colgate University.
Jay Golon
Pollyanna Program Designer & Facilitator
Jay Golon is an educator with 20 years of experience as a teacher and administrator in independent schools. He currently works with Pollyanna’s clients to design and facilitate workshops that advance the work of equity and justice.
Jay believes that all students flourish in just, equitable, and identity-safe learning environments. Ensuring that every child and family can be the fullest, most authentic version of themselves in all of their communities is at the heart of his work as an educator.
He spent the first part of his career in the classroom as a Middle School Social Studies teacher at the Trevor Day School in New York City, the Epiphany School in Dorchester, Massachusetts, and The Dalton School in New York City. He also served as Dalton’s Middle School Assistant Director for Curriculum and Dean of Students for five years followed by three years as Middle School Principal at the Friends School of Baltimore.
Jay earned a B.A. from Wesleyan University in American Studies and Theater and a Masters in School Leadership from Harvard University.
Claire Hannan-Radomisli
Pollyanna Director of Operations
Claire Hannan-Radomisli joined Pollyanna in 2018 as a Project Manager and eventually took on the role of Director of Operations. Much of her work involves partnering with schools to plan and develop Pollyanna conferences for their communities.
She served as President of the Parents Association at The Dalton School from 2013-2015. During her tenure, Claire promoted community building and inclusion, and supported the many diversity/affinity groups at the school. She was instrumental in establishing the New Parent Welcome Committee, the Gay and Lesbian Parent Group, and the Hispanic/Latino Parent Group. In addition, Claire served as a Trustee and was a member of the following Board committees: Community Life & Diversity and New Trustees. She has volunteered at the Dalton Diversity Conference for many years and attended the Glenn Singleton training, “Beyond Diversity.”
Claire graduated Summa Cum Laude from N.Y.U. with a BS in Cultural Anthropology. Much of her coursework focused on the study of gender, identity, race, religion, sexual orientation from a global perspective.
Claire lives in New York with her husband and their three boys.
Jason Craige Harris
Pollyanna Senior Advisor
Jason Craige Harris is an educator, speaker, facilitator, and leadership advisor who partners with K–12 schools to cultivate cultures of dignity, belonging, and transformation. A former classroom teacher and senior administrator, as well as a trusted coach to school leaders, Jason supports educators, administrators, students, and families in building trust, navigating conflict, and leading with purpose and care.
Drawing on insights from ethics, psychology, and systems thinking, Jason helps school communities foster inclusive environments where all students and adults can thrive. He is a recognized expert in restorative practices and pedagogy, ethical leadership, and dialogue across lines of difference—and a sought-after speaker known for his powerful storytelling, deep empathy, and practical wisdom.
Whether he is leading professional development for faculty, facilitating hard conversations among students, or advising senior leadership teams, Jason equips communities with the tools to prevent harm, repair breakdowns, and sustain a culture rooted in respect and shared purpose.
Shernice Lazare
Pollyanna Strategist and Facilitator
Derek Lipscomb
Project Coordinator
Derek Lipscomb is an educator, athlete, consultant, and community organizer in Harlem. He has worked as an educator for over 15 years as a teacher, administrator, and diversity practitioner in New York independent schools as well as playing rugby for the Brooklyn Kings and the US national team. In 2019, he cofounded Roots Rugby, an Afrocentric rugby team focused on community outreach and identity development. With his background in education and sports, Derek seeks to bridge communities across New York to center curiosity, empathy, and advocacy across ideological differences.
Anthony Witte
Pollyanna Facilitator
Anthony is the founder of Witte’s End Consulting, where he brings twenty years of experience as an educator and practitioner in diversity, equity, inclusion, and belonging (DEIB). He focuses on helping organizations create more inclusive and equitable cultures. His work spans schools, nonprofits, and corporate settings, guiding communities from awareness to meaningful action. As a multiracial person of Chinese, European, and Jewish heritage, Anthony brings a personal and intersectional lens to conversations around identity, belonging, and building sustainable practices together.
He is a founding member of the San Francisco Equity Leaders, a board member of 18Doors and Sequoia Living, and an ex-officio member of Northern California People of Color in Independent Schools. Anthony has presented at national conferences and is the co-author of Diversity Work in Independent Schools and Belonging: Assessing the ‘B’ in DEIB Work.
Sarah Woods
Marketing Strategist
Sarah is a strategic communications advisor who helps mission-driven organizations use communications effectively to support their priorities.
At Pollyanna, she led marketing for the inaugural Pollyanna National Conference and contributed to the organization’s 10-year anniversary. She continues to shape and strengthen communications and marketing across the organization.
With more than 25 years of experience across nonprofit, education, and corporate sectors in New York, Hong Kong, and London, she brings a thoughtful, practical approach. She works closely with senior teams on messaging, positioning, and marketing, helping to make sure their communications are clear, consistent, and aligned with their goals.
Board of Trustees
Pollyanna’s Board of Trustees provides thoughtful governance, strategic guidance, and steadfast stewardship in support of our mission.
Comprised of leaders from a range of professional backgrounds and experiences, the Board plays an essential role in helping Pollyanna grow with integrity, purpose, and long-term vision. Their leadership helps ensure that our work remains both mission-driven and responsive to the evolving needs of the communities we serve.
We are deeply grateful for their service, partnership, and shared commitment to Building Stronger and Kinder Communities.
Rena Andoh
Rena Andoh is a litigation partner with Sheppard, Mullin, Richter & Hampton LLP in New York. Her broad practice ranges from complex commercial and trade secret/restrictive covenant enforcement cases to False Claims Act cases to intellectual property cases arising out of government contracts. Rena acts as first chair trial counsel in jury trials and arbitrations, and argues in appellate courts, including the District of Columbia Circuit Court of Appeals and the First Department of the New York State Supreme Court, Appellate Division.
Rena is an active supporter of Sheppard Mullin’s diversity and inclusion initiatives. She serves as vice-chair of the Attorneys of Color Success Initiative Committee (“ACSIC”), convened by the chair of Sheppard Mullin to advance the firm’s practices and programs to recruit, retain and promote attorneys of color and LGBTQ attorneys. She also vice-chairs Sheppard Mullin’s Diversity & Inclusion Committee. Rena is a 2015 Leadership Counsel for Legal Diversity (“LCLD”) Fellow, and is an active alumni and mentor in the LCLD organization.
Mia Burton
Mia Burton is an experienced facilitator, consultant and counselor with expertise in developing and leading equity and justice initiatives. In her role as Director of Institutional Equity and Inclusion at Flint Hill School, she leads the development and implementation of policies and programs that sustain an inclusive, equitable, and just school community. Her desire to be a change agent led her to establish MSB Advising to advise organizations and support individuals committed to visionary and transformational equity goals. Ms. Burton earned a bachelor’s degree from the University of Virginia with a double major in English and African & African-American Studies. She received her master’s degree in School Counseling from Marymount University.
Casper Caldarola
Pollyanna Founder
Casper Caldarola founded the New York based, non-profit, Pollyanna in 2015. Casper has worn many hats in independent schools: alum, parent, administrator, and trustee, and saw different levels of commitment to DEI work. She felt and still feels the most important aspect of this work is to keep the academic, social, and emotional needs of the student at the center. Casper founded Pollyanna to support the schools that have made a commitment to building a more inclusive school community through multi-constituent conference models, workshops, community assessments and racial literacy curriculum.
Casper’s experience includes serving as president of the Dalton School Parents Association. During her tenure, she created a more inclusive community, developed a new budgeting structure making it possible for parents of different socioeconomics to volunteer, hosted more events at school to take the pressure off of in-home hosting, and introduced monthly topic-driven parent discussions to find additional ways to bring the community together. In addition, Casper was the Communications Director at the Allen-Stevenson School and was tasked with helping to develop and implement equity initiatives, such as, developing a more inclusive hiring process and creating Parent Chats with topics that focused on DEI. Before joining the independent school world, she was a marketing and advertising executive.
Casper now serves on the Board of Seeds of Peace. She was a trustee at the Dalton School for 10 years and served as a member of the Executive Committee, chaired the Committee on New Trustees and Community Life & Diversity Committee, and was on the strategic plan steering committee, and has also served on the boards of Parents-in-Action and Generation Citizen.
Emerson Casper, Jr trustee
Currently a college student and a former Pollyanna Teen Council leader.
Veneka Chag
A s Director of Investor Relations at Blue Meridian Partners, Veneka helps cultivate strong relationships with Blue Meridian’s General and Impact Partners, builds an engaging learning environment for the Partner group, and supports efforts to engage prospective investors in advancing the organization’s mission. She provides strategic and operational leadership in close collaboration with the Chief Strategic Development and Governance Officer, CEO, and other senior leaders to design and implement high-impact fundraising strategies that deepen Blue Meridian’s reach and amplify its impact.
Before joining Blue Meridian, Veneka served as Managing Director of Development at KIPP NYC, where she led the organization’s capital campaign, drove fundraising strategy, built and stewarded major donor relationships, and worked closely with board members to secure critical resources for organizational growth. Prior to that, she played a key role at Princeton University, managing high-value donor portfolios and leading both international and domestic fundraising initiatives. She collaborated with trustees and senior institutional leaders to secure philanthropic investments that advanced the university’s strategic priorities. Veneka has also worked with philanthropic organizations including The Rockefeller Foundation and served as a consultant to The Ford Foundation, advising on initiatives aimed at driving systemic, long-term change.
Veneka brings deep expertise in philanthropy, fundraising, and relationship management, leveraging her cross-sector experience to advance Blue Meridian’s mission. She holds a BA in Public Affairs and International Relations, with a minor in East Asian Studies, from Princeton University, and an MBA from the University of Virginia’s Darden School of Business.
Paquita Davis-Friday
Paquita Y. Davis-Friday is the Dean of the Massry School of Business at the University at Albany. She earned her Ph.D. and Master in accounting, M.A. in Applied Economics and B.B.A from the University of Michigan-Ann Arbor.
Rebecca Gamzon
Rebecca Danziger Gamzon is an experienced educator who has worked and volunteered in public, private and charter schools. She recently served on the Board of Trustees at her alma mater, the Spence School, where she helped lead the Diversity, Equity and Inclusion committee and served as Vice President of its Parents’ Association. Rebecca was a founding member of the Framers Board of Civics Unplugged, a national leadership and civic engagement program for high school students. She earned her Master of Science in Early Adolescence from Bank Street College of Education and a Bachelor of Arts from Yale University in American Studies.
Alessandra Gouldner
Alessandra Gouldner is on the Boards of School of America Ballet, Catskill Arts Society and Dance Gallery Festival Board.
Celeste Herrera
Celeste Herrera is Head of School at The Calhoun School on Manhattan’s Upper West Side, a progressive institution known for social justice and experiential learning. Previously at The Dalton School, she led equity-focused initiatives and held leadership roles including Assistant Head of School. A UNC Chapel Hill and University of Pennsylvania graduate, Celeste also worked in admissions at Penn. She and her husband, Ken, live in NYC with their three children and are committed to educational equity.
Destynée Johnson
Currently at Cornell University, and was a Pollyanna intern leading Pollyanna Teen Council.
Oliver Kramer
Oliver Kramer is a writer and producer of film, television, and theater. Oliver’s screenplays have been commissioned by major producers in Los Angeles, New York and London.
Addeson Lehv
Addeson Lehv was our inaugural Jr. Trustee while he was a junior and senior at Trinity School. He currently attends Columbia University.
Deepti Mittal
Deepti Mittal brings substantial interest, commitment and experience with non-profit organizations. She has worked in the areas of gender justice, education and the environment. Deepti is the founder of The Mittal Talwar Team at Douglas Elliman. She is also a partner of a consulting firm, Teamqore, which helps clients optimize their core management areas to make their vision a reality.
Erica Pettis
Erica Pettis is a fundraising professional based in New York, NY. With over a decade in the industry, she now works as a consultant helping non-profits reach their fundraising goals and deliver on their mission.
Tal Recanati
Tal Recanati is an entrepreneur and non-profit advocate who has spent the past 15 years championing causes that promote dialogue, cultivate leaders and provide grass-roots solutions to societal issues.
Pankti Sevak
Pankti Sevak, currently the Head of School at San Francisco Friends School, has devoted her professional life to fostering what she calls “the magic of school.” A graduate of Cornell University with a Bachelor of Science in Biological Sciences and a Master of Arts in Teaching, she has a broad range of teaching and administrative experiences.
Jim Wilson
Jim Wilson has spent 20+ years in executive management with a track record of success in building talented teams and launching, scaling and transforming businesses. His experience includes entertainment and education software, video, music and advertising. He also has extensive not for profit and other board experience.