WSPEF <> AWSP <> sideby

LEARNING IN STRIDE

Washington School Principals Education Foundation logo with text and six colored circles.
Logo of the Association of Washington School Principals featuring a stylized flame in blue, green, and orange colors.
Logo with a pink and white stylized eraser and the word 'sideby' in beige letters.

Learning in Stride is a statewide learning system that equips education leaders with human-centered AI skills through continuous, job-embedded, practice-based learning.

Our Relationship

The Washington School Principals Education Foundation (WSPEF) is a 501(c)(3) nonprofit dedicated to strengthening school leadership in Washington in service of students and communities. WSPEF partners closely with the Association of Washington School Principals (AWSP), the statewide professional association for principals and assistant principals. The two organizations share leadership and collaborate on grant-funded leadership development and equity initiatives. Founded in 1972, AWSP provides trusted statewide reach and professional learning infrastructure supporting nearly all school leaders in Washington. AWSP serves as the primary field-facing delivery partner, engaging principals and district leaders, integrating Learning in Stride into existing professional learning structures, and acting as the visible convener and implementer.

sideby serves as the learning design and technology partner, supporting the development and delivery of human-centered, AI-enabled learning pathways, peer learning experiences, and evidence capture. Building on two years of partnership with AWSP, this project accelerates our collaborative approach to innovative professional development. Together, WSPEF, AWSP, and sideby combine nonprofit governance, statewide leadership infrastructure, and applied learning technology to deliver responsible, scalable AI upskilling for education leaders.

Our Plan

If funded through the WIN AI Challenge—a national initiative supporting women’s leadership and workforce readiness in an AI-shaped economy—Learning in Stride will launch as a statewide AI learning system for education leaders. The grant will enable AWSP and sideby to embed human-centered, responsible AI practice into daily leadership work by building durable learning pathways, expanding facilitator capacity, and supporting leaders through short, peer-based sessions that translate AI concepts into real decisions affecting schools, staff, and students.

Women make up approximately 59% of AWSP’s membership, yet persistent barriers in access to AI learning and engagement risk widening gaps in influence, readiness, and advancement as AI reshapes education systems. Without intentional, job-embedded AI upskilling, these disparities can compound across schools—affecting classrooms, student outcomes, and the long-term diversity and strength of senior education leadership statewide and across collaborative networks.

Our Solution

Flowchart titled "How Learning in Stride Works" explaining structured AI learning embedded in leadership practice, with steps including getting matched with a peer, engaging in a live session, receiving an idea, sharing a practice win, building badge or clock hours, and stacking badges into learning pathways. The diagram has icons with colorful illustrations and arrows showing process flow.

Pilot and Sample Badging

Banner with logos of the Association of Washington School Principals and sideby, with text 'Advancing Digital Equity', themed for the March 26, 2026, event. The banner features a colorful compass rose symbol.
Logo of the Association of Washington School Principals (AWSP) and sideby partnerships, with a yellow banner reading "Human-Centered AI in Education," and a colorful geometric star emblem at the bottom.
A graphic displaying the logos of the Association of Washington School Principals and Sideby, with large yellow banners stating "AI-Enabled Feedback" and an emblem with four colored sections below.
Banner with logos of AWSP and sideby, with yellow banners containing the text 'AI for Continuous Improvement', and a colorful compass symbol at the bottom.
A banner for an event on AI and leadership organized by the Association of Washington School Principals and sideby, featuring their logos at the top, colorful banners with text, and a multicolored compass-like symbol at the bottom.
A banner featuring the logos of the Association of Washington School Principals and sideby, with the text 'AI for Operational Sustainability' and a compass icon at the bottom.
Infographic titled 'Early Evidence and Statewide Partnership' showing data on badge completion and retention rates, with a logo for AWSP and sideby. Features charts indicating positive engagement and application.

Promising traction, ready for scale

Why Learning in Stride?

  • ✺

    Designed by School Leaders for School Leaders

    Learning in Stride is built by former principals and district leaders who understand the realities of schools. Every learning experience is grounded in real leadership practice—not abstract theory or tools alone.

  • ✺

    What Leaders Asked For: Real Connection

    AWSP leaders consistently report feeling isolated in their roles. Learning in Stride creates structured, trusted peer connections where leaders can think together about complex, high-stakes decisions shaped by AI.

  • ✺

    Learning That Counts Toward Certification

    Leaders earn clock hours through authentic, job-embedded learning—not compliance-driven coursework. Learning is meaningful, recognized, and aligned to professional standards.

  • ✺

    AI Learning That Fits the Workday

    Traditional professional development doesn’t fit leaders’ schedules—especially women balancing caregiving and leadership demands. Learning in Stride uses short, guided sessions embedded in daily work.

  • ✺

    From Individual Insight to Network Impact

    Learning doesn’t stop with one leader. The platform captures shared ideas, small wins, and patterns of practice—amplifying learning across the statewide leadership network.

  • ✺

    Keeping Women Leaders From Falling Behind

    Women make up nearly 60% of Washington’s school leaders, yet face persistent barriers in accessing AI learning. Learning in Stride ensures women leaders build AI skills, confidence, and influence—without sacrificing time, wellbeing, or advancement.

Flowchart titled 'How AI Learning Scales Across Leaders' showing the stages of growth toward AI learning becoming a reusable system for learning with multiple interconnected groups of people.

How Does sideby Really Work?

An infographic titled "Learning Building Blocks" describing elements that make up side-by-side learning experiences, including sideby Sessions, Session Ideas, Small Win Stories, Curated Content, Experiential Learning Tasks, and Solo Reflection Sessions.
A flowchart titled 'A Learner's Experience' illustrating a learning process. It includes steps: side-by-side session, receive an idea or next step, try it in context, notice what happens, capture a small win, feel or see progress, and repeat. Each step is represented with icons and arrows connecting them.
An infographic titled "Evidence of Learning" explaining four ways to capture authentic learning: transcripts, small wins, artifacts, and visible growth, with colorful icons for each.

✺ Frequently asked questions ✺

  • Learning in Stride is planned to launch following funding through the WIN AI Challenge, with award decisions anticipated in Fall 2026. If funded, early opportunities to participate will be shared with AWSP members.

    We know this will be a competitive grant process, and we may also seek additional funding sources. We should know if we have moved forward in the initial grant process by Spring 2026.

  • Learning in Stride is designed for education leaders, including principals, assistant principals, and aspiring leaders. Priority access will be provided to AWSP members, with intentional focus on women leaders. As capacity grows, participation may expand to leaders across the School Leadership Collaborative and, over time, to additional states and national partners.

  • Learning in Stride is embedded into leaders’ daily work. Participants engage in short, guided peer sessions and reflection cycles designed to fit within existing responsibilities—rather than adding separate coursework or long workshops.

  • No. Learning in Stride is designed for leaders at all experience levels. Pathways begin with foundational understanding and focus on practical, responsible application, not technical skill or coding knowledge.

  • Yes. Learning in Stride is designed to align with professional learning and clock-hour requirements. Participants can earn clock hours through completed sessions and badge-based learning, tracked within existing credentialing systems.

  • Learning in Stride is a partnership between the Washington School Principals Education Foundation (WSPEF), the Association of Washington School Principals (AWSP), and sideby.

    The project is led by a collaborative team including Scott Friedman of AWSP, Erica Crane, EdD,‍ ‍Mike Mendelson, and Kippy Smith of sideby. Together, the team brings experience as former educators, principals, system leaders, and designers of large-scale, job-embedded learning.

    Watch this short video to meet the team and learn why they’re building Learning in Stride here.

    If you have additional questions or would like to be in touch about this project, you can contact erica@sideby.ai or andi@awsp.org.