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 is the Founder of Pollyanna, a national nonprofit dedicated to Building Stronger and Kinder Communities in schools. Since 2015, she has partnered with schools across the country to align mission, values, and daily practice through conferences, leadership development, curricula, and community assessments. Drawing on her experience as an alum, parent, administrator, and trustee, Casper believes meaningful change happens when entire communities engage in shared learning and collective responsibility. She previously served on the Board of Trustees at The Dalton School, SEEDs of Peace, Parents in Action NY, Generation Citizen, and held a leadership role at Allen-Stevenson. Before founding Pollyanna, she built a successful career in marketing and advertising.
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.
Jason Craige Harris
Pollyanna Senior Advisor
Jason Craige Harris is a thought leader, strategist, and storyteller who helps leaders and some of the sharpest minds in the country solve hard problems. When organizations and communities are stuck, polarized, or quietly unraveling, Jason is often the person called in to help steady the room, fix what’s broken, and help people talk to each other again. Trained in ethics, psychology, and systems thinking, he blends science with real life—using humor, deep listening, and storytelling to help people navigate conflict, repair relationships, and make decisions under pressure. A researcher, mediator, and restorative practitioner, Jason studies how stress, power, and fear hijack our conversations—and how curiosity, dignity, courage, and spiritual practice can bring us back. A Pollyanna speaker, he brings big ideas down to earth, helping people see that leadership isn’t about being the loudest or the smartest—it’s about being human, especially when it’s hardest. Jason also serves as CEO of Perception Strategies, a boutique strategy consulting firm. He holds degrees from Wesleyan University and Yale Divinity School.
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.
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.
Katie Rocker
Facilitator & Project Manager
Katie Rocker is the founder of Katie Rocker Leadership Solutions. She helps leaders and teams thrive by amplifying their strengths for greater success and fulfillment. Katie coaches individuals and teams across educational, corporate, and nonprofit sectors — including Fortune 500 companies and independent schools — and leads workshops focused on strengths-based leadership, team dynamics, and resilience. With nearly two decades of independent school experience, including 11 years as a division head, she understands what it takes to nurture thriving school communities. Katie holds degrees from Williams College and Harvard (Ed.M.) and is credentialed through Gallup CliftonStrengths and UC Berkeley’s Executive Coaching Institute.
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 Benesch Law 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 also has deep experience in the Diversity, Equity & Inclusion field, having spent years as Chair of Diversity & Inclusion at her prior firm. She routinely consults with clients on policies, initiatives and best practices. New York University School of Law, 2003, J.D., University of Michigan, 1995, B.M.
Ava Azoulay
Ava joined Pollyanna’s Teen Council as a seventh grader at Village Community School and has remained an engaged and committed leader through her senior year at Fieldston. Over the years, she has grown into a thoughtful facilitator and a skilled, confident interviewer, helping elevate student voice within the organization. Ava will attend the University of Southern California in the fall of 2026. Ava is a Jr. Trustee.
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 Assistant Head of School for Community, Equity, and Student Success 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. Mia 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 is the Founder of Pollyanna, a national nonprofit dedicated to Building Stronger and Kinder Communities in schools. Since 2015, she has partnered with schools across the country to align mission, values, and daily practice through conferences, leadership development, curricula, and community assessments. Drawing on her experience as an alum, parent, administrator, and trustee, Casper believes meaningful change happens when entire communities engage in shared learning and collective responsibility. She previously served on the Board of Trustees at The Dalton School, SEEDs of Peace, Parents in Action NY, Generation Citizen, and held a leadership role at Allen-Stevenson. Before founding Pollyanna, she built a successful career in marketing and advertising.
James Calleroz White
Dr. James Calleroz White is the Head of School at Dwight-Englewood School in Englewood, New Jersey. A nationally respected educational leader, he brings more than three decades of experience across independent schools, higher education, and nonprofit organizations. Prior to joining Dwight-Englewood, he served as Head of School at The Galloway School in Atlanta and Louisville Collegiate School in Kentucky, and held senior leadership roles at Phoenix Country Day School, Belmont Hill School, Harvard College Admissions, Prep for Prep, and Sponsors for Educational Opportunity. Dr. Calleroz White currently serves on the board of the National Association of Independent Schools (NAIS) and has been a faculty member and facilitator for NAIS leadership institutes. He holds degrees from Harvard University and Arizona State University and is deeply committed to educational excellence, leadership development, and inclusive school communities.
Emerson Casper
Emerson Casper is a student at Lafayette College majoring in Government & Law and Psychology while pursuing a pre-law track. A former leader of the Pollyanna Teen Council, Emerson remains committed to fostering dialogue, leadership, and belonging among young people. On campus, Emerson serves in student government, coordinates DEI Peer Educators, and is Vice President of Diversity, Equity, and Inclusion for the Panhellenic Council. Through these roles, Emerson works to strengthen community, support student engagement, and advance inclusive practices across campus. Emerson is a Jr. Trustee.
Veneka Chag
As Director of Investor Relations at Blue Meridian Partners, Veneka Chag helps cultivate relationships with Blue Meridian’s General and Impact Partners, supports engagement with prospective investors, and collaborates with senior leadership to advance the organization’s mission and fundraising strategy. Prior to joining Blue Meridian, Veneka held leadership roles in development and fundraising at KIPP NYC and Princeton University, where she worked closely with donors, trustees, and institutional leaders to secure philanthropic investments and support organizational growth. She also brings experience working with major philanthropic organizations, including The Rockefeller Foundation and The Ford Foundation. Veneka holds a BA in Public Affairs and International Relations from Princeton University and an MBA from the University of Virginia’s Darden School of Business.
Christina Clemente
Christina Clemente joined The Brearley School in July 2023 as the Director of Middle and Upper School Admission and Financial Assistance. Prior to joining Brearley, Ms. Clemente was the director of enrollment management at the Evergreen School in Shoreline, WA. In addition, she has worked at Hackley School and Brooklyn Friends School, where she first began her career in independent school admission. A native New Yorker, Ms. Clemente is an alumna of the Dalton School and a graduate of Amherst College. She has a master’s degree in educational psychology from Hunter College.
Paquita Davis-Friday
Dr. Paquita Y. Davis-Friday is the Dean of the Massry School of Business at the University at Albany and Chair of the Board of Pollyanna, Inc. Before joining UAlbany, she served as a visiting senior research scholar at Columbia Business School and held several leadership roles at Baruch College’s Zicklin School of Business, including interim dean, senior associate dean, and executive director of Graduate Programs. Her research focuses on executive compensation and postretirement benefits and has been published in leading accounting journals. She earned her PhD in Accounting, M.A. in Applied Economics, and joint MAcc/BBA degree from the University of Michigan-Ann Arbor. She also serves as Chair of the Advisory Board of the New York City Independent Budget Office.
Marsha Elliott
Marsha Elliott is a seasoned educator with over two decades of experience across esteemed independent schools. She currently serves as a member of the senior administrative team in her role of Director of Equity and Inclusion at St. Stephen’s Episcopal School. Throughout her career, she has held various positions, including English teacher, diversity coordinator, dorm parent, and advisor, while leading faculty/staff professional development, school-wide student-centered activities and programming, restorative conversations, and identity, alliance, and culture groups, alongside planning curriculum and facilitating sessions for regional and national education conferences. A graduate of Rice University (B.A.) and Boston College (M.A.), Marsha remains deeply committed to building equitable, inclusive school communities that amplify student voices and honor the dignity of every individual.
Emily Gottlieb
Emily Gottlieb is an attorney who serves as Deputy Director for Law and Policy at the Center for Justice & Democracy, a nonprofit dedicated to safeguarding the U.S. civil justice system. Her work focuses on consumer advocacy and policy research, translating complex legal issues into actionable analysis. Emily also brings nearly 20 years of volunteer leadership and governance experience at educational institutions. She is a graduate of the Dalton School, Swarthmore College, and Brooklyn Law School.
Alessandra Gouldner
Alessandra Gouldner is a passionate advocate for the arts with deep roots in entrepreneurship and nonprofit leadership. For 25 years, she ran AG Interiors, her interior design company, specializing in creative space design, client relationships, and business management. She also currently serves on the boards of the School of American Ballet, the Catskill Arts Society, and the Dance Gallery Festival. Alessandra is also the founder of the Ardsley Dance Residency, a contemporary choreographic residency dedicated to nurturing emerging talent and advancing the field of dance. Through her board service, community engagement, and longstanding commitment to diversity and inclusion, she works to expand access to the arts and strengthen cultural institutions. Alessandra is honored to serve as a trustee of Pollyanna.
Jason Craige Harris
Jason Craige Harris is a thought leader, strategist, and storyteller who helps leaders and some of the sharpest minds in the country solve hard problems. When organizations and communities are stuck, polarized, or quietly unraveling, Jason is often the person called in to help steady the room, fix what’s broken, and help people talk to each other again. Trained in ethics, psychology, and systems thinking, he blends science with real life—using humor, deep listening, and storytelling to help people navigate conflict, repair relationships, and make decisions under pressure. A researcher, mediator, and restorative practitioner, Jason studies how stress, power, and fear hijack our conversations—and how curiosity, dignity, courage, and spiritual practice can bring us back. A Pollyanna speaker, he brings big ideas down to earth, helping people see that leadership isn’t about being the loudest or the smartest—it’s about being human, especially when it’s hardest. Jason also serves as CEO of Perception Strategies, a boutique strategy consulting firm. He holds degrees from Wesleyan University and Yale Divinity School.
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, share a passion for education; Ken has devoted his career to charter school growth and reform. The two live in NYC with three children, two grumpy rescue dogs, and a collective commitment to educational equity.
Destynée Johnson
Destynée Johnson is a recent graduate of Cornell University and former Pollyanna intern. During her time with Pollyanna, she played a leadership role in supporting the Pollyanna Teen Council and helping to create meaningful opportunities for student voice and engagement. Destynée brings the perspective of a recent student leader and remains passionate about empowering young people to contribute to positive change in their schools and communities.
Addeson Lehv
Addeson Lehv served as Pollyanna’s inaugural Jr. Trustee while a student at Trinity School in New York City. In that role, he helped ensure that student perspectives were represented in board discussions and organizational planning. He is currently a student at Columbia Law School and serves as Vice Chair of a Manhattan Community Board 2. Addeson remains committed to civic engagement, public service, and creating opportunities for young people to contribute meaningfully to their communities.
Saya McKenna
Saya McKenna is the Head of School at the Drew School in San Francisco, where she previously served as Assistant Head of School for Academics. She spent two decades at Head-Royce School in Oakland, serving in multiple leadership roles and co-founding the Institute for Applied Learning. An award-winning English and History teacher, she has been recognized for excellence in teaching and leadership. A Stanford graduate with a credential from San Francisco State, Saya brings over 20 years of experience in education. Saya lives in San Francisco with her husband, Paul, and their two daughters.
Victor Peng
Victor joined Pollyanna’s Teen Council at the beginning of high school. He attends University School of Nashville and is graduating this year and will attend Vanderbilt in the fall. Victor is one of our most thoughtful leaders, always willing to step in and help, facilitate, write thank you notes to our guests and anything else needed. Victor is a Jr. Trustee.
Erica Pettis
Erica Pettis is a fundraising professional based in New York, NY. With more than a decade of experience in the field, she works as a consultant helping nonprofits achieve their fundraising goals and advance their missions. Much of her professional work has focused on independent schools, where she has supported development efforts and institutional growth. She is also involved in fundraising for the Barrett County Library and is passionate about helping mission-driven organizations build the resources needed to sustain and expand their impact.
Tal Recanati
Tal Recanati has held leadership and advisory roles across public health, democracy, education, and peacebuilding. She currently serves on the board of the Alliance for Middle East Peace (ALLMEP), the largest network of Palestinian and Israeli peacebuilders, and previously served as Vice Chair of the Board of Seeds of Peace, where she chaired the Nominations Committee. She also chaired the Advisory Committee of the Arnhold Institute for Global Health at the Icahn School of Medicine at Mount Sinai. Tal is a passionate advocate for dialogue, reconciliation, and civic engagement. She produced the critically acclaimed documentary Germans & Jews (2016), which explores Germany’s efforts to confront its Nazi past. Today, her philanthropic work focuses on strengthening liberal democracy, supporting peacebuilding initiatives, and advancing opportunities for dialogue across difference. She holds a B.A. from Washington University in St. Louis and an LL.B. from University College London.
Chai Reddy
Dr. Chai Reddy is an experienced educational leader with more than two decades of experience in independent schools as a teacher, coach, administrator, and advocate for global education. He currently serves as Head of High School at University School of Nashville, where he leads faculty, supports students and families, and advances academic excellence and community engagement. Previously, he served as Director of the Upper School at Beaver Country Day School and spent 14 years at Punahou School, where he led the growth of global education initiatives and international learning opportunities. Chai is passionate about leadership development, curriculum innovation, and creating inclusive learning environments. He holds degrees from Creighton University, John Carroll University, and Lake Forest College.
Pankti Sevak
Pankti Sevak, former the Head of School at San Francisco Friends School, has worked in schools for almost three decades, devoting 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, previously serving as both the Middle School Head and Dean of the Faculty at Friends Seminary, a K–12 Quaker school in New York City. Until her move to the West Coast, Pankti also served as a faculty member and director for the Divisional Leadership Institute of the New York State Association of Independent Schools.
