Our Team

Meet our staff, board, and advisors and explore job opportunities in our organization.


Lindsay Baerg
Research Assistant

Lindsay Baerg, M.Ed., is a Research Assistant with Challenge Success. She works on data analysis, specifically in regards to all things qualitative. Lindsay started as a Research Intern with Challenge Success during her senior year in college and she has a passion for student education, mental health, and overall well-being. She has experience in higher education as she is also an Academic Advising Specialist at Belmont University. Lindsay has a B.S. in Psychology from Santa Clara University and a M.Ed. in Human Development Studies from Vanderbilt University.

Kimberly Cawkwell
Director of Programs

Kimberly Tsai Cawkwell, M.Ed., A proud first-generation Taiwanese immigrant, mother, educator, and creative, Kimberly Tsai Cawkwell has served over thirteen years in the education ecosystem. As a current adjunct-faculty member at the High Tech High (HTH) Graduate School of Education and Director of Programs at Challenge Success, Kim is deeply honored to serve in spaces that cultivate Deeper Learning pedagogy in service of nurturing equitable spaces within K-12 schools.
Growing up as a multilingual learner in a semi-isolated motel next to a busy New Orleans expressway, living through the duality of American and Taiwanese cultures, and experiencing teaching and learning in variety of settings around the globe, Kim has developed a unique lens for culturally responsive environments and an insatiable desire to center student voices in classrooms. Through the opportunities to learn from students in her own classrooms to students from diverse corners of our globe, Kim believes deeply in student-driven transformative learning that sparks a common love and joy to seek knowledge. As she continues to support systemic change that lifts up student voices and honors the passions and identities of all students, Kim is grateful for the invaluable knowledge gained from others, holds humility as a practitioner and mentor for Deeper Learning practices, and is continuously inspired by the beautiful humans who are called to serve youth.
Prior to joining Challenge Success, Kim was a founder of two High Tech Elementary (HTe) schools, a former colleague at the University of San Diego and New Tech Network, and a public servant in the Pasadena and San Diego regions. She holds a B.A. from the University of Riverside and M.Ed from the University of California, San Diego. When she’s not designing and facilitating learning, Kim might be found spending quality time with her two daughters, loving spouse, and family in Oceanside, San Gabriel, and Taichung. Learn more about Kimberly Tsai Cawkwell on Twitter @mskimcawkwell.

Caitlin Ciannella
Director of Development & Communications

Caitlin Ciannella, M.A.,  is the Director of Development and Communications for Challenge Success, overseeing the organization’s philanthropic support from donors, foundations, and grantmakers as well as strategic communications for the organization. She brings over a decade of nonprofit experience to the role,  including working with schools and other nonprofits to expand their development, marketing, and communications efforts. She is passionate about supporting  organizations that serve children and families and partnering with philanthropists to drive meaningful change.

Margaret Dunlap
Senior School Design Partner,
Transformative Coaching & Leadership

Margaret Dunlap, M.A., is a Senior School Design Partner. She oversees the operation of the School Program, providing coordination, resources, and management to Challenge Success schools on the West Coast. Additionally, she plans the bi-annual Challenge Success school conferences and supports coaches and school site teams to promote best practices and policy reform. She has extensive experience in professional development, supervision, evaluation, and intensive coaching for teacher leaders, coaches, and novice teachers. Margaret has held various roles in education leadership and program management within public and private education for over 20 years.

Laura Easley
School Design Partner

Laura Easley, M.Ed., is a School Design Partner. She has worked in Chicago Public Schools, New York City’s public schools, Boston Public Schools, Denver Public Schools, and for Summit Learning and Summit’s Bay Area schools before coming to Challenge Success. She has taught students from PK to graduate level, and worked on curriculum development and assessment practices with state and national standards in 28 districts in 16 states. Her not-so-secret passion is arts integration curricula, but she loves any and all project-based curricula. She believes every student should be able to see their identities reflected in their curriculum and in potential pathways to individual success.

Kristen Edge
Marketing & Events Manager

Kristen Edge, M.A., is the Marketing & Program Operations Manager for Challenge Success. She handles marketing initiatives for the organization, event coordination, and systems management for program operations. Prior to her work at Challenge Success, she was an event and marketing coordinator for national natural food brands, and before that, she taught high school and college English and Composition. Her graduate work was in rhetoric and digital media studies with a focus on nonprofit marketing.

jon kleiman
Jon Kleiman
Senior School Design Partner,
Strategic School Partnerships

Jon Kleiman, M.A., is a Senior School Design Partner. He oversees the operation of the school program, providing coordination, resources, and management to Challenge Success schools on the East Coast. Jon has worked in the education space in several capacities, from creating curriculum for the opening of a school for Rwandan women to developing and teaching design thinking courses to undergraduates.

tricia mcentee
Tricia McEntee
Director of Finance and Operations

Tricia McEntee, B.A., CPA is the Director of Finance and Operations for Challenge Success where she is responsible for overseeing finance, human resources, and internal operations.  Previously, Tricia spent over a decade as the Executive Director and CFO of the Esalen Institute, an iconic center for exploring and realizing human potential. Tricia began her career in public accounting with Ernst and Young, continuing into increasingly more responsible positions as CFO in various for-profit and non-profit organizations. She believes in the power of a holistic approach to human development and well-being to unleash our unlimited capacities of creativity, curiosity, and connection.

Cordy McJunkins
Research Assistant

Cordy McJunkins is a Research Assistant with Challenge Success. He works on data collection, management, and analytics for the organization on student mental health and well-being. Cordy is currently a graduate student at Stanford University pursuing a dual master’s program in education policy and public policy.

sara miles
Sarah Miles
Director of Research

Sarah Miles, M.S.W., Ph.D., is the Director of Research for Challenge Success. She oversees the organization’s Research team, leads research efforts on how schools and classrooms can best support student learning and engagement, and partners with Challenge Success member schools to translate research into practice. She also presents at conferences and writes articles for education-related journals. She has served as a coach with Challenge Success member schools and worked as a teaching and research assistant at Stanford. Prior to receiving her doctoral degree, Sarah taught fifth grade in Oakland, California and worked as a clinical social worker in the Boston area.

Anika Mohan
Research Intern

Anika Mohan is a junior at Irvington High in Fremont, CA, and will be working as a research intern this semester. Prior to working with Challenge Success, she conducted an independent research project studying
the impacts of the pandemic and distance learning on youth motivation and socioemotional learning. Outside of research, Anika also enjoys teaching STEM classes to through her nonprofit, Yobea, horse riding, and singing. 

Sarah O’Meara Gonzalez
Administrative Associate

Sarah O’Meara Gonzalez is the Administrative Associate for Challenge Success. She provides administrative support to operations, finance and fundraising. Prior to joining Challenge Success, she worked in higher education at the University of Connecticut and Rutgers providing grant management and departmental support. She has a deep passion for education and revisioning how schools measure success to include student well-being.  

Megan Pacheco
Executive Director

Megan Pacheco, M.A., is the Executive Director for Challenge Success. She has more than 20 years of experience helping to transform schools.  She has served in a variety of roles, including teacher, school coach, and organizational leader.  Prior to joining Challenge Success, she was the Chief Learning Officer for New Tech Network, a national network of schools focused on deeper learning. She is passionate about ensuring all students experience a meaningful, equitable, and inclusive learning environment.  Her primary focus has been organizational leadership, school design, project-based learning, continuous improvement, and curriculum and assessment.  Megan has a B.S. in Mathematics and an M.A. in Mathematics Education.

denise pope
Denise Pope
Co-Founder and Strategic Advisor

Denise Pope, Ph.D., is a Senior Lecturer at the Stanford University Graduate School of Education. She is the author of, “Doing School”: How We Are Creating a Generation of Stressed Out, Materialistic, and Miseducated Students (Yale University Press, 2001), which was awarded Notable Book in Education by the American School Board Journal, 2001, and co-author of Overloaded and Underprepared: Strategies for Stronger Schools and Healthy, Successful Kids (Jossey-Bass, 2015). Dr. Pope lectures nationally on parenting techniques and pedagogical strategies to increase student health, engagement with learning, and integrity. She is a three-time recipient of the Stanford University School of Education Outstanding Teacher and Mentor Award and was honored with the 2012 Education Professor of the Year “Educators’ Voice Award” from the Academy of Education Arts and Sciences. Prior to teaching at Stanford, Dr. Pope taught high school English in Fremont, CA and college composition and rhetoric courses at Santa Clara University. She lives in Los Altos, CA with her husband and three children.

Drew Schrader
School Design Partner

Drew Schrader, M.Ed., is a School Design Partner. He has worked to help educators across a wide range of contexts redesign their systems around deeper learning for all students with a particular focus on project-based learning and authentic assessment. Prior to working at Challenge Success, he served as the Director of Assessment and a School Development Coach for New Tech Network. He was also a founding teacher and local teacher advocate at The Academy of Science and Entrepreneurship in Bloomington, IN. He has particular interests in improvement science and organizational change.

samantha selby
Samantha Selby
Research Associate

Samantha Selby, M.A., is a Research Associate with Challenge Success. She manages and supports the quantitative and qualitative data analysis of school surveys and supports the organization’s overall research efforts. Samantha has experience as an environmental education research associate and a social science researcher, during which she was the project co-coordinator and co-teacher of an environmental leadership program in rural Costa Rica. Prior to working as a researcher, Samantha taught at a non-profit, tuition-free middle school in Arizona and taught English in Spain. 

eric spaly
Eric Spaly
Director of Strategic Initiatives

Eric Spaly, M.B.A., is the Director of Strategic Initiatives, focused on major projects to support the organization’s growth and impact. For over 20 years Eric has helped leaders at Fortune 500 companies, investment firms and smaller organizations with M&A, operations and strategy. He has previously worked at Bain & Company, JP Morgan & Co, and as a volunteer at several education organizations. 

Gary Alpert

Gary Alpert, M.B.A., is the Chief Strategy Officer & Head of Business Development at Brightline, the leader in technology-enabled pediatric behavioral health care that is reinventing the way behavioral health is delivered to children, teens, and their families. Gary is a serial entrepreneur who has built, led, and grown client-facing teams at the fastest growing digital health companies. Prior to Brightline, Gary ran the Client Success team at Livongo, a leader in chronic disease management, with responsibility for managing, renewing, and expanding Livongo’s F1000 client base. He also led Customer Success and Solutions Consulting at Castlight Health, a leading health benefits navigation platform. He holds an M.B.A and a B.A. in Human Biology. Gary and his wife have raised two daughters in the Bay Area and frequently turn to books and advice by the Challenge Success team for parenting wisdom.

Mike Barker

Mike Barker is currently the director of institutional research at Harvard-Westlake. In this role he orchestrates the school’s overall research agenda and supports analytic and planning capacity across all administrative functions. Prior to  Harvard-Westlake, Mike worked in a similar capacity at Phillips Academy Andover as the Director of Academy Research, Information, and Library Services.  Prior to Andover, Mike spent nine years working at Harvard University in their library system, finishing his time there as the Director of Financial Planning and Analysis.  Mike holds a BA from the University of San Diego and an MLS from the Simmons College Graduate School of Library and Information Science.  Mike has a wife Jenny and children Greta and Cale.

Lisa Busby

Lisa Busby, M.A., is a private educational consultant as well as the Senior Strategy Advisor for Phillips Brooks School in Menlo Park, where she served previously as the Associate Head of School. This role followed sixteen years at San Francisco Day School, where she was the Director of High School Counseling and Strategic Plan Implementation Coordinator. Lisa has led the development of school programs and strategic initiatives that nurture student health, intrinsic motivation, creativity, and cultural competence. She has counseled 1000+ Bay Area families in their application processes for 6th grade through college, with a focus on balancing their academic and extracurricular goals with social-emotional needs. Lisa has served on the boards of California Poets in the Schools and The Lobster Theater Project, the latter as Board President. She holds a B.A. and M.A. in English Literature and a certificate in School Management and Leadership.

Mark Boswell

Mark Boswell currently serves as the founder and CEO of Bewake, a educational consulting firm focused on the nexus of education, equity, and justice. Prior to starting Bewake, Mark worked closely with Joe Feldman (Grading for Equity) and the Crescendo Education Group supporting educational institutions in making systems of grading more equitable, has served in multiple roles as a school administrator, taught at both the primary and secondary level, and has developed professional development opportunities specifically for educators of color. When his face is not in a book, you can find him trying to keep up with his partner and 3 daughters in Atlanta, GA or trying to solve the world’s problems by baking the perfect biscuit while listening to music from the 70s. Mark holds an MA in Private School Leadership and a B.A. in Political Science and Economics. 

Jenny Fan Raj

Jenny Fan Raj is a writer whose work examines the intersection of marginalized voices and the humanity that connects all of us. Her work has been nominated for the Pushcart Prize in fiction and published in the New York Times, The Columbia Journal, and The Laurel Review, among others. Prior to writing, Jenny worked as a design thinking consultant at IDEO, where she focused on blue sky strategy, product development, and ethnographic research. Jenny also serves on the board of Youth Speaks, a Bay-Area based nonprofit that creates spaces for youth to develop and amplify their voices as creators of societal change. Jenny holds a B.A. in Japanese Literature and a M.Des in Design Planning. In her free time, she enjoys reading, traveling, and perfecting the art of layer cakes. She lives in San Francisco with her husband and two children. 

Sofi Frankowski

Sofi Frankowski serves as the Chief Learning Officer for Schools That Lead, a hub for networks of K-13 public schools collaborating to address inequities and improve student experiences and outcomes. She has taught elementary, middle school and high school students in Connecticut, Washington DC, Japan, California and North Carolina. Her leadership has been shaped by a belief in the power of adult collaboration and a commitment to improving outcomes for all students. A National Board Certified teacher, Frankowski holds a B.A. in public policy studies and an M.A. in education. She lives in Raleigh, NC with her two curious, adventurous middle school kids.

Meeta Gaitonde

Meeta Gaitonde is currently the Director of Admission for Phillips Brooks School in Menlo Park, which has been her second home since 2002, when she started her career in education as a teacher. She chairs the Diversity, Equity, Inclusion Committee at Phillips Brooks created to identify strategies to ensure the school is committed to creating and sustaining a diverse, inclusive, equitable, and just community. Meeta also serves on the board of the Bay Area Directors of Admission (BADA). She holds a B.A. in Economics. In her free time, she enjoys reading, sports, Indian classical dance and music, and time with family and friends. She is a Bay Area native and currently lives in Menlo Park with her husband and two children.

Taylor Griffin

Taylor Griffin currently serves as communications manager for Global Affairs at Spotify, a global audio streaming service, devising strategic policy communications for the company.  Prior to joining Spotify, Taylor served as Press Secretary to House Speaker Nancy Pelosi where she assisted in directing strategic communications, message development and digital strategy for the Speaker and the House Democrats for six years. Taylor holds a bachelor’s degree having studied Government, French, and African American Studies with a Certificate of Political Studies from a political science institution in Lyon, France. She is a proud San Francisco Bay Area native and currently resides in Brooklyn, NY.

Andrew Housiaux

Andrew Housiaux,M.T.S., is the Currie Family Director of the Tang Institute at Phillips Academy (Andover, MA), where he also teaches Philosophy and Religious Studies. His work supports faculty learning and curricular innovation, both at Andover and across networks of educators in public, private, and charter schools. He has two degrees in religion and has been a fellow with the National Endowment for the Humanities and the Program in Religion and Public Life at Harvard Divinity School. He is also a founding lead of FORGE, a program for teachers at the Klingenstein Center of Teachers College. His writing and research explore ways to help adolescents lead more reflective and moral lives. Andrew and his spouse have a toddler who keeps them busy and happy.

Sharon Olken

Sharon Olken, M.A., is the Executive Director of Gateway Public Schools in San Francisco, where she has worked for 20 years as a teacher, school leader and school founder. Gateway Public Schools leads two schools, Gateway Middle and Gateway High, as well as Gateway Impact, an initiative that shares Gateway’s best practices and brings educators together to collaborate and learn from one another through conferences, speaker series, and digital publications. Gateway’s schools serve 800 students who represent the rich diversity of San Francisco and help them discover their unique potential, what they love, and the impact they hope to make on their communities. Annually, more than 96% of Gateway’s diverse graduates attend college, more than double the statewide rate. Sharon recently founded Everyday Leadership, a website dedicated to providing models of positive leadership and helping others cultivate their power and voice. Sharon loves her work because she sees education and leadership as two essential tools for personal growth and social change. Sharon holds a B.A. and an M.A. in Education. She lives in San Francisco with her wife, Nancy.

Rachel Skiffer

Rachel Skiffer, J.D., was most recently the Head of School at Khan Lab School (KLS) in Silicon Valley, a mastery-based K-12 independent school founded by Sal Khan in 2014. She is the Head-Elect of Head-Royce School in Oakland. Prior to KLS, Rachel was the Dean of Policy & Strategic Planning at Phillips Academy (Andover, MA), and previously worked in admissions and financial aid at San Francisco University High School, the Latin School of Chicago, and Harvard College. Before discovering her passion for education, Rachel spent time as a management consultant and a commercial real estate attorney. She has an A.B. in Women’s Studies and holds a J.D. A native of San Francisco, Rachel lives in the Bay Area with her husband and their two young children.

Jeff Symonds

Jeff Symonds, M.A., is the Director of Teaching and Learning and Tukman Distinguished Teacher of English and Music at The Branson School in Ross, CA. In his 28 years there, he has worn just about every community hat; most recently, he has helped to design a Shakespeare and Social Justice class that gives students the opportunity to work with inmates at San Quentin, and helped design and write the school’s strategic plan. Jeff is also a musician who has played a gig in 47 of the continental states (apologies to Alabama).

Kelli Tomlinson

Kelli Tomlinson, B.A., focuses her time in the non-profit sector as Director and Co-President of the Tomlinson Family Foundation. She is Chair of the Board of Trustees at The Girls’ Middle School, a progressive, STEM-focused girls school in Palo Alto, California. Tomlinson also serves on the boards of the Berkeley Repertory Theatre, and The Art of Yoga Project. She and her family are partners at the Silicon Valley Social Venture Fund. She is a member of the Common Sense Media Bay Area Council and the Peninsula Bridge Parent Advisory Board. Her primary interests include progressive education, education equality, and theater. She holds a B.A. in political science and worked as the assistant director of the Trinity in San Francisco Program from 1998 to 2001. She resides in Atherton, California, with her husband and their two children.

Sally Whipple

Sally Whipple, B.S.,has been involved in youth development through the summer camp experience for over 25 years.  She and her husband own and direct Mountain Camp, Mountain Camp-Woodside, and Farm Camp, three traditional camp programs in Northern California that intentionally integrate social-emotional learning into their programs. Sally believes in the power of community and volunteering, and has served as president of the Moraga Education Foundation (MEF) and PTA.  In her seven years on the MEF Board of Directors, Sally implemented its first strategic plan, met annual fundraising goals, and doubled the endowment. Sally holds a B.S. in Microbiology and Single Subject Teaching Credential in Biology, and taught science at Stuart Hall School for Boys in San Francisco. In addition, she is a 500-hour registered yoga teacher and enjoys hiking, camping, traveling, and healthy living.  Sally lives in Moraga with her husband and two teenage boys.   


High School Junior | Denville, NJ

Why are you excited to work with the Challenge Success Student Advisory Committee?
I am excited because Challenge Success is something that is truly interesting. Reducing stress in ways that are manageable for high school students is important.


College Freshman | Boston, MA

Why are you excited to work with the Challenge Success Student Advisory Committee?
I think that the student voice has a powerful impact if it is displayed correctly, and the student advisory committee does a great job of bringing together students from all over and engaging their perspective in the work of Challenge Success.


High School Sophomore | Irvine, CA

Why are you excited to work with the Challenge Success Student Advisory Committee?
I am excited to work with the Challenge Success Student Advisory committee because making a change for the better in our society is important to me. I love how this program prioritizes students’ mental health, and helps better the well-being of students.


College Freshman | Los Angeles, CA

Why are you excited to work with the Challenge Success Student Advisory Committee?
We live in a society where school is important–so important that students often lose sight of why they do specific extracurriculars and take specific classes. The vigor of student schedules takes a toll on student mental health, resulting in a loss of passion for learning. By being on the committee, I hope to help give advice, provide perspective, and help make a difference to those who are struggling. Success is important to all of us, but being happy and in good mental health is more important.


High School Junior | Denville, NJ

Why are you excited to work with the Challenge Success Student Advisory Committee?
I am excited to be a part of the Challenge Success Student Advisory Committee because having started Challenge Success in my school, I can see the impact of student voice, and I want to create that in other schools as well.

Kenneth R. Ginsburg

Kenneth R. Ginsburg, M.D. is a pediatrician specializing in Adolescent Medicine at the Children’s Hospital of Philadelphia, and is a professor of pediatrics at the University of Pennsylvania School of Medicine. He is a Director of Health Services at Covenant House Pennsylvania, a shelter for homeless and marginalized youth. He has written extensively promoting teen health and resilience, including the books Reaching Teens: Strength-based, Trauma-sensitive, Resilience-building Communication Strategies Rooted in Positive Youth Development. He has also produced and edited the multimedia professional toolkit, Reaching Teens: Strength-based Communication Strategies to Build Resilience and Support Healthy Adolescent Development. His definitive memorandum for the American Academy of Pediatrics, The Importance of Play in Promoting Healthy Child Development and Maintaining Strong Parent-Child Bonds, formed the basis for his congressional testimony in May 2007.

Annie Hall

Annie Hall, J.D., is a governance attorney serving mostly non-profit organizations committed to child and adolescent wellness. She Co-Chairs Newton-Wellesley Hospital’s Resilience Project Advisory Council. The Resilience Project is part of the Child/ Adolescent Psychiatry Department at NWH and is committed to improving access to mental health services. She was very pleased to bring both organizations together for NWH’s Educational Summit. 

Rabbi Patricia Karlin-Neumann

Rabbi Patricia Karlin-Neumann came to Stanford University in 1996. She is the first university chaplain from a tradition other than Christianity in Stanford’s history. In 2001, she was appointed Senior Associate Dean for Religious Life. She teaches and lectures widely on Jewish feminism, rabbinical ethics, the relationship between religion and education, and social justice. She was ordained at the Hebrew Union College-Jewish Institute of Religion in 1982. She has been a Hillel director and Jewish chaplain at UCLA and at the Claremont Colleges, a congregational rabbi in Alameda, California, and a Regional Director for the Union for Reform Judaism, the congregational arm of the Reform Movement. At Stanford, she teaches courses including “Spirituality and Nonviolent Social Transformation” and “Rereading Judaism in Light of Feminism.” She is married and has two children.

Michael Keller

Michael Keller, Ed.D., is the Director of Social and Emotional Support in the Laguna Beach Unified School District. He leads school-based mental health professionals and the health services teams in implementing systems of care TK-12.  He is a licensed educational psychologist and nationally certified school psychologist and earned his doctorate of education in educational leadership and educational psychology. Michael has taught advanced graduate courses on trauma and grief counseling in the schools, positive behavior assessment and interventions, and learning theory at the University of Southern California and CSU Long Beach. He has presented nationally at conferences in school-based mental health and model programs in applied social and emotional learning. He lives in Long Beach with his wife and two children.

Nick Kovacs

Nick Kovacs spent seven years as Head of Upper School and is currently the Deputy Headmaster at Crescent; an all-boys school located in Toronto, Canada. Nick oversees the day-to-day operations of the Lower, Middle and Upper Schools and is responsible for launching and leading strategic initiatives in the areas of academic planning, health and well-being, and community diversity. Previously, Nick worked as a teacher and Vice-Principal at St. Michael’s Choir School (Toronto), taught and held various leadership positions at Neil McNeil High School (Toronto), Mentor College (Mississauga), and Vandyke Upper School (Leighton Buzzard, UK).

Alex Lockett

Alex Lockett, M.B.A., is the Head of Upper School at Crystal Springs Uplands School. Prior to this role, she served as the Dean of Students at San Francisco University High School for 13 years. A lifelong native of independent schools, Alex is motivated by the desire to help students bring their whole selves to school and to help teachers feel equipped to respond to the needs of their students in and out of the classroom. Alex enjoys studying systems and holds a bachelor’s degree in Biology and an M.B.A. with a focus in Educational Leadership. She lives in San Mateo with her husband and two children.

Patricia Russell

Patricia Russell is an experienced educator and was the Dean of Studies at Phillips Academy in Andover, MA when she joined the board of directors of the Mastery Transcript Consortium in 2016. She was the founding interim executive director and currently serves as the MTC’s Chief Education Officer.

Rebecca Sacerdoti

Rebecca Sacerdoti, Ph.D., is a clinical psychologist who has significant experience working with adults and teens in a variety of settings, including private practice, agency work, and in schools. Her research experience stems from time spent as a Project Director in the Department of Psychiatry at Stanford University. Rebecca currently works in private practice in San Francisco. As a mother of two girls and as a clinician who works with teens, her support of Challenge Success is both personal and professional. Rebecca is acutely aware of the pressures at play for teens and believes Challenge Success is the antidote because it offers schools, public and private, concrete ways to support, buffer and inspire teens. More importantly she believes it holds the potential to radically alter the current trajectory of the teenage experience on a national level.

Brad Sachs

Brad Sachs, Ph.D., is a psychologist, educator, consultant, lecturer, and best-selling author specializing in clinical work with children, adolescents, couples, and families. He is the Founder and Director of The Father Center, a program designed to meet the needs of new, expectant, and experienced fathers. He has published numerous books and articles for both professional and lay readers, including The Good Enough Child: How to Have an Imperfect Family and Be Perfectly Satisfied and Family Centered Treatment with Struggling Young Adults. Brad is also a published poet, composer, and performer. He wrote Hard Tales to Tell, a cycle of sixteen original songs based on stories his patients have told him and a book of poetry, Why Am I Telling You This? And Other Poems From Psychotherapy.

Catherine Steiner-Adair

Catherine Steiner-Adair, Ed.D., is a leading expert specializing in child development, education, and family relationships. She speaks and consults on a wide range of topics, including social and emotional intelligence, health and well-being, leadership education, and nourishing healthy relationships in the digital age and developing a thoughtful approach to technology in school and life. She is a longtime “fan” and colleague of Challenge Success, Denise Pope, and Madeline Levine, as well as a CS Conference keynote presenter.

Pamela Kading Webb

Pamela Kading Webb, M.P.P., has been actively involved with Challenge Success since 2013, launching and implementing the program at Dover-Sherborn Regional Schools (K-12), the first CS Member School on the East Coast. Pam co-chaired the CS Initiative at Dover-Sherborn, served as the Chair of Parent Programs on the Dover-Sherborn CS Team, has worked with numerous other CS schools in a coaching capacity as well as presented parent engagement workshops at our national conferences. She has over three decades of experience working with nonprofit organizations in an executive management or volunteer leadership capacity. Most recently, in her role as a Board Member of Community Action Partners at Harvard Business School, Pam oversees pro bono consulting projects for nonprofit clients in the Greater Boston area. Pam earned a Master’s in Public Policy specializing in Child/Family Policy and Education.

Matt Wulfstat

Matt Wulfstat served as the head of Stratford School for nearly a decade leading the private independent school’s growth from 6 to 18 campuses and 200+ to 800+ faculty and staff.  He currently serves on educational boards including ISG (a subsidiary of International Student Services, ISS has served private schools around the world for over 60 years), KSS (a growing group of immersion language schools in the US) and Brandeis Marin (a K-8 private school in Northern California).  Matt is a former Wexner Heritage Fellow and Young Presidents Organization (YPO) member and has been a speaker at national conferences on educational investment and innovation.  Matt earned an MBA, MA in Education and BA.  He has four children and is a longtime fan of Challenge Success’ work as both a professional and a parent. 

Calla Griffith

Calla Griffith is a committed ambassador for the health and well-being of kids in the local community and beyond. She has over 20 years of fundraising and event planning experience, and significant expertise in making an impact in the non-profit sector through building awareness, developing allies, and raising funds for organizations across the Bay Area, including the Children’s Health Council, Menlo Park City School District, and Lucile Packard Children’s Hospital. She currently lives in Menlo Park, CA.

Leigh Sherwood Matthes

Leigh Sherwood Matthes is a native New Yorker with a 15-year history in marketing and advertising between NYC and Los Angeles. Currently she is an active philanthropist and real estate developer. She serves on the National Advisory Board of the Haas School of Public Service based at Stanford University as well as the Advisory Board of Every Mother Counts, a NYC-based global organization whose mission is equitable maternal health care for all. Leigh also serves on the Slide Ranch Advisory Board whose mission is to connect children to nature to foster future environmental stewards. She is a past Director of Holsted Marketing, a NYC-based direct marketing firm and a past trustee at the UCSF Foundation, the Katherine Delmar Burke School, and the Bay Area Discovery Museum.  She was also a member of the UCSF Cancer Council, the Center for Childhood Creativity, and Convent of the Sacred Heart Advancement committee. Leigh lives in the Bay Area with her husband and two children.


We’re always looking for talented people to join our team. Explore our open positions or reach out to us directly with your resume and tell us why you’d be a great addition to our team: jobs@challengesuccess.org


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