Get to Know Me
My resume gives you a timeline, but there is so much more to me. Let's plan
a visit and I will tell you about my time with Disney, the farm, and how I once heard Keith Richards play with
Walter Wolfman Washington .
WINIFRED O’LEARY
Education, Arts & Community Program Leader
CONTACT
Program Strategy & Development | Arts & Adult Learning | Community Engagement | Curriculum & Professional Learning | Partnerships | Program Evaluation | Project & Operations Management | Technology & AI
Education and arts program leader with 30+ years of experience designing learning experiences, building programs, engaging communities, and translating ideas into effective practice. Background spans curriculum and adult learning, program strategy, community partnerships, and implementation, complemented by a B.A. in Art History and hands-on leadership of arts education, visual arts, and community programs. Experienced in building programs from the ground up, leading complex initiatives, developing partnerships, and using data and community feedback to strengthen impact.
EXPERIENCE
Amira Learning/Istation
2024-2025
Success Manager | Academic Delivery & Implementation Leadership
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Partnered with leaders in more than 100 districts to develop implementation strategies connecting program goals, educator practice, student data, and organizational priorities.
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Analyzed student performance and usage data to identify opportunities and inform program decisions.
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Created district-facing reports, implementation summaries, and executive communications translating assessment data and program insights into actionable recommendations.
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Developed implementation resources, coaching frameworks, and professional learning experiences that strengthened adoption and sustainability.
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Advised district leaders in evaluating implementation progress, identifying barriers, and developing strategies to improve program impact.
Kindness Collective
2023 - present
Director of Curriculum and District Implementation
Built the instructional vision and implementation strategy for a national K–6 kindness initiative, designing curriculum, educator resources, and professional learning systems that helped schools create meaningful student experiences.
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Designed and developed a scalable K–6 curriculum model, educator resources, and professional learning supporting district adoption.
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Developed implementation systems supporting district readiness, sustainability, and continuous improvement.
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Partnered with educators and organizational leaders to gather feedback, refine resources, and ensure programming reflected school and community needs.
Edmentum
2005-2023
Progressive Leadership Roles:
Manager of Educator Engagement & Academic Initiatives |
National Intervention Consultant |
Senior Curriculum Implementation Consultant |
Educational Consultant
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Founded and scaled a national educator network from concept to more than 3,000 members, creating a community that informed product development, professional learning, and organizational initiatives.
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Designed and facilitated educator think tanks connecting teachers, administrators, and organizational leaders to identify challenges, share solutions, and influence future strategies.
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Served as a bridge among educators, curriculum teams, product teams, and organizational leaders, translating classroom experience, implementation trends, and learning data into program improvements and resources.
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Partnered with district and organizational leaders to align curriculum, intervention, professional learning, and implementation with student and organizational needs.
Early Career
1992-2006
Teacher | Adjunct Professor | Inclusive Preschool Program Director
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Designed and led inclusive early learning programs integrating curriculum, family partnerships, and individualized approaches for diverse learners.
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Created and directed an early inclusive preschool model, developing programming and collaborating with families and educators to support children with diverse developmental and educational needs.
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Taught and mentored adult learners in early childhood education and teacher preparation.
Arts & Community Programming
ART CAMP FOR GROWN-UPS | Founder & Program Director | 2024–Present
Design and lead an annual weekend adult arts retreat for 3–4 participants, developing original projects and lesson plans and managing programming, materials, meals, scheduling, communications, and the complete participant experience.
MAKE ART A WILD ART SALON | Founder & Curator | 2025–Present
Created and launched a public multimedia art salon as the foundation for an ongoing community arts program, bringing together eight local artists who exhibited and spoke about their work for approximately 75 community members. Cultivate relationships with artists and sponsors and manage curation, event planning, communications, logistics, and production.
LAKE-A-THON | Founder & Community Event Director | 2009–Present
Founded and lead an annual community fundraiser now in its 18th year. Originally organized to support the local food bank and Ronald McDonald House, the event evolved into a scholarship initiative that has raised more than $60,000 for the Peggy O’Leary Seigler Scholarship Endowment Fund and supported a medical student scholarship awarded annually for 11 years. Lead fundraising, donor and vendor relationships, marketing, volunteers, programming, purchasing, and day-of operations.
COMMUNITY & GOVERNANCE LEADERSHIP
Elected to public school board; participated in strategic planning, budget oversight, policy development, curriculum and personnel decisions, administrative leadership, facilities planning, and community
Thought Leadership:
SXSW EDU & ISTE Presenter |
Published Author |
National Webinar & Podcast Presenter |
Contributor to National Education Publications
EDUCATION
Mary Washington University BA
Art History
University of New Orleans M. ED
Curriculum and Instruction
Montclair University
Studies in Special Education
Resume
Work
Experience
Professional Skills
SKILLS
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Instructional Leadership & Adult Learning
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Proficiency in Data-Driven Decision Making
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Influences and Champions Shared Strategy
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Curriculum Design & Implementation
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E-Learning & Educational Technology
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Strategic Program Development
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Standards-Aligned Curriculum Development (K–12)
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Professional Learning Design & Facilitation
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Educational Program Leadership
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Historical & Cultural Education Outreach
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Partnership Development & Stakeholder Engagement
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Strategic Data Collection & Program Evaluation
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Writing & Publication for Educator Audiences
TECHNOLOGY
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Camtasia
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Canva
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YouTube
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Social Media Platforms
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Google Suite
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Word Suite
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SalesForce
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Bizzabo
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ClickUp
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Asana
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Trello
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Wix
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Variety of Classroom Management and Instructional Tools
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AI programs for Art, Writing and Lesson Planning
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Variety of other digital tools for creating, polling, organizing, producing and engaging.
Montclair State University
Studies in Special Education
University of New Orleans MEd
Master of Curriculum &
Instruction
Mary Washington College
BA Art History
Amira Learning/Istation
November 2023-October 2025
Customer Success Manager
Lead district-scale instructional improvement efforts by aligning curriculum, instructional delivery, and assessment to strengthen learner outcomes.
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Partner with district instructional leaders and faculty teams to ensure high-quality implementation aligned to competency goals and learner needs.
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Use learning data, pacing metrics, and student performance indicators to guide academic decisions that improve instructional delivery and support mastery.
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Facilitate reflective practice cycles with instructional teams to calibrate expectations, refine teaching strategies, and ensure consistency across classrooms and campuses.
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Establish operational systems—playbooks, schedules, meeting structures—that support clarity, accountability, and equity in academic delivery.
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Build trust and alignment across principals, district leaders, and vendor partners to sustain high-quality instructional ecosystems.
Kindness Collective
2023 -present
Director of Curriculum and Program Implementation
Oversee academic delivery across partner districts, leading teams responsible for curriculum, instruction, and educator development.
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Manage faculty-facing professional learning, instructional coaching structures, and collaborative planning processes across multiple districts.
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Develop curriculum-aligned instructional models and evaluation expectations to ensure consistent and equitable delivery.
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Lead cross-functional teams through data reflection protocols, identifying patterns in student performance and guiding responsive changes in instruction.
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Create documentation systems, alignment tools, and instructional frameworks that support coherence across contributors and programs.
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Support faculty and instructional teams through change processes, ensuring adoption of new practices and technologies with clarity and purpose.
Edmentum
2005-2023
Manager of Educator Engagement and Initiatives,
National Intervention Consultant
Senior Curriculum Consultant
Educator Consultant
April 2005 - March 2023,
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Led national educator networks, faculty-facing learning systems, and instructional quality initiatives that influenced student outcomes across hundreds of districts.
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3,000+ educators, strengthening instructional practice and assessment literacy.
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Led cross-functional teams integrating educator voice into curriculum, assessment design, and instructional models, ensuring alignment to CBE principles and academic goals.
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Guided district instructional leaders in interpreting learning data to refine teaching strategies, pacing, and student support systems.
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Built faculty communities of practice, fostering collaboration, reflective practice, and shared ownership of student success.
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Shaped go-to-market and academic strategies by establishing consistent playbooks and instructional expectations across product and learning teams.
National Intervention Consultant | Senior Curriculum Implementation Consultant
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Provided direct instructional leadership support to large districts, guiding faculty teams through adoption, calibration, and continuous improvement cycles.
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Developed and facilitated professional learning to strengthen teacher practice, deepen assessment analysis, and align instructional decisions with student needs.
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Maintained academic fidelity across multi-phase implementations through clear documentation, instructional walkthrough structures, and success metrics.
Educational Consultant
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Designed standardized instructional protocols and faculty-support systems used across multiple districts.
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Facilitated PD cycles, coaching engagements, and educator collaboration that improved instructional quality and strengthened student engagement.
Educator Adjunct Professor Early Childhood Education Designer and Lead Instructor -Inclusion Model Preschool Program Lead Teacher of the Handicap (Autistic, MSDD, PDD) Classroom Teacher
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Roles included preschool program designer, lead teacher for specialized populations, and adjunct professor.
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Developed inclusive instructional frameworks, aligned curriculum with learner needs, and supported faculty development across early education and special education settings.
NOTABLE LEADERSHIP & IMPACT
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National Faculty Influence: Presented large-scale instructional sessions to audiences of 5,000+, published thought leadership in EdSurge and Edutopia, and guided national conversations on curriculum, assessment, and instructional practice.
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Founder of a 3,000-Member Faculty Network: Built and led a national association that fostered educator collaboration, professional learning, and curriculum alignment.
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Academic Governance: Elected member, Bloomingdale Board of Education—provided oversight on curriculum, instruction, and student services.
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Thought Leadership: Designed and led a three-day think tank for administrators, faculty, and academic innovators.
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Advocacy: Long-standing advocate for families navigating special education systems.