Media & Stories

sideby Impact Report 2025

In 2025, sideby supported educators across 34 states and 12 countries, facilitating 387 peer learning sessions and impacting more than 500 classrooms. Through structured 1:1 conversations, AI-supported reflection, and badge-based learning pathways, educators didn’t just participate—they applied their learning in practice. With completion rates far exceeding typical online courses and strong evidence of real-world implementation, this year affirmed our core belief: professional learning sticks when it’s visible, social, and grounded in daily work.

sideby is a Launch Startup Competition Semifinalist

sideby was named a semifinalist in the SXSW EDU 2026 Launch Startup Competition, recognizing our work to make professional learning visible, social, and grounded in real practice. The Launch competition highlights early-stage education companies driving meaningful innovation, and we’re honored to be included among global leaders shaping the future of learning.

sideby is selected for USC Rossier’s EdTech Accelerator (Cohort 8)

sideby was selected as one of sixteen companies worldwide to join Cohort 8 of USC Rossier’s EdTech Accelerator, a highly competitive program supporting education ventures with strong potential to improve quality and equity in learning. Through the Accelerator, sideby is collaborating with USC faculty, industry advisors, and fellow innovators to strengthen our impact and accelerate growth—ensuring that our approach to practice-based, human-centered professional learning continues to serve educators and learners at scale.

Khan Lab School AIED Summit 2025

Mike recently led a hands-on workshop at the innovative Khan Lab School AIED Summit, where educators from across the country gathered to explore the future of AI in education. Mike guided participants through practical strategies for leading AI integration in ways that position students as creators, critical thinkers, and engaged citizens. We’re grateful to partner with communities pushing the boundaries of what’s possible in teaching and learning.

Human-Powered AI for Social Good: Learning with HundrED’s Youth Ambassadors

Erica recently co-hosted a powerful workshop, Human-Powered AI for Social Good, alongside Marta Pinto for the Global Youth Ambassadors at HundrED. Together, they explored how AI is shaping young people’s day-to-day lives—and how it can (and can’t) support meaningful social mapping and strategic planning for youth-led projects. We’re inspired by the thoughtfulness and leadership of these Youth Ambassadors and grateful to collaborate with partners who are centering human agency in the age of AI.

Maine Tech Week 2025

Kippy recently spoke at Maine Tech Week’s Education Technology Roundtable, joining leaders from across the state to explore how innovation and AI can strengthen teaching and learning. Drawing on her experience founding Small Wins Dashboard and now serving as sideby’s Senior Vice President of Learning, Kippy shared how schools can become true learning organizations—grounded in continuous improvement, professional collaboration, and human-centered design. We’re proud to contribute to conversations that are shaping the future of education in Maine and beyond.

10 Actionable AI Strategies & Practices from Educators

Developed through our AI Onward Badge cohort, this collection captures real strategies educators are using to ensure AI supports deeper learning—not speed or automation. From critically reviewing AI outputs and cross-checking tools for bias, to designing AI use that strengthens student reasoning and ownership, these practices reflect what responsible, human-centered AI looks like in action. Explore the full set of community-sourced strategies and success indicators shaping equitable AI use in classrooms today.

Give Teachers The Learning You Want For Students

At sideby, we know teachers deserve the same kind of rich, reflective, and empowering learning we want for students. In this Association of Washington School Principals (AWSP) blog, sideby team members highlight how transformational professional learning can drive real school improvement. sideby works with the AWSP on connecting members along learning pathways tied to their leadership framework.

Insights from the Small Wins Dashboard

The Small Wins Dashboard blog shines a light on how everyday progress fuels big change—helping educators capture growth, reflect on practice, and build collective momentum toward bold goals. From practical strategies to inspiring stories, it turns small wins into powerful lessons for leaders and teams. Now part of the sideby family, the blog continues to share insights that complement our shared mission of amplifying educator genius and transformational learning.

Transformational Professional Learning Drives Deeper Student Learning

When educators experience transformational learning, students benefit. This blog post looks at how reflective, collaborative professional development strengthens teaching, fosters student agency, and builds the metacognitive habits essential for deeper learning. This is the final blog post in our three part series on transformational professional learning and how our commitment to this approach underscores how we develop learning experiences in sideby and the Small Wins Dashboard.

Trends we’re seeing on sideby

Educators aren’t using AI to hustle harder, they’re using it to protect what matters. sideby community members are sharing how they are leveraging AI to set boundaries, reclaim their time, and prioritize sustainability. Educators are sharing how going home on time isn’t about doing less, it’s about doing the right things, with care.

The Impacts of Transformational Learning for Educators

Schools spend thousands per teacher on professional development, but one-off workshops rarely lead to real change. Just ask teachers. Transformational professional development does. It shifts mindsets, boosts morale, and builds sustainable growth by centering educator agency and authentic reflection. sideby and the Small Wins Dashboard help make that growth visible, actionable, and lasting.

This is how learning sounds on sideby…

Get a taste of how it sounds on sideby when the community is connecting. Individual matches are happening with guided prompts at the bottom of the screen. Community members are collaborating, sharing their wins and challenges, and discussing how they’re applying AI in real classrooms and schools.

You’ll hear the buzz of educators leaning into hard conversations with curiosity. There’s laughter, long pauses of thought, aha moments, and affirmations. It’s the sound of people being seen and supported in their work.

Why Educators Deserve Transformational Professional Learning

Most PD is transactional — sit, get, and forget. But educators deserve learning experiences that transform how they think, lead, and teach.

At sideby, we believe professional learning should reshape not just practice, but identity. That’s why our one to one peer learning model centers agency, authenticity, and critical reflection.

Transformational professional learning should be the norm for educators. At sideby, it is.

sideby Sundays from our co-founder & cto

Learn about the phases of learning from a real nerd and his nerdy students who worked to define the learning process together. At sideby, we’re focused on Phase 3, where learners can benefit from connecting with another human (even with all the many non-human tools available).

💭 “That’s why my life’s work since then has been about this: giving learners more ways to install Phase 3 into their lives. Because there will always be categories of learning that require another human to help wrap your head around.”

Big news: sideby and the Small Wins Dashboard are officially joining forces.

Together, we’re doubling down on tools that amplify educator genius through both 1:1 peer learning and tracking the small wins that drive big change. With Kippy Smith now leading learning at sideby, we’re just getting started on building the future of transformational PD.

sideby Sundays from the Building Thinking Classrooms Conference 2025

Mike shared about his experience at the annual BTC conference for over 800 educators in this week’s sideby sundays. He engaged with mathletes at the interactive Thinker and Tinker Space, met sideby community members in person, heard helpful feedback that’s already informing our development, and celebrated Monique Pollitt and the Puget Sound ESD team that hosted this incredible learning experience.

AWSP / WASA Conference 2025

Erica represented the team at this annual conference for over 2,200 education leaders from Washington state. We also got to meet some awesome sideby community members in person! At our booth, we heard from principals, vice principals, deans, curriculum coordinators, and superintendents about the conversations they’re having around AI in their schools. Check out the trends we found in shared grapples and insights.

sideby Sundays with our co-founder & cto

This week’s sideby sundays reflects on what a once-a-year pond skim can teach us about learning: not the kind you cram, but the kind you build over time. sideby cofounder mike mendelson shares what it means to stay in it, try again, and trust that real understanding takes repetition, timing, and a willingness to fall.

💭 "Because I’m going to stay in it, I’m going to learn, eventually, to take some funny vehicle across this pond."

sideby Sundays with our co-founder & cto

In this week’s sideby sundays, our cofounder & cto Mike Mendelson reflects on a year of teaching AP Precalculus where test prep came last, not first. Two weeks out, his students are just now diving in. Why wait? Because sometimes, the best learning comes from cutting late.

💭 "Maybe, condensing the time where we focus on the test might be a part of the answer to the question: what's the right balance of testing and teaching the good stuff."

The 2025 AI Innovation Summit

Our co-founder and CTO Mike Mendelson led sessions at the AI Innovation Summit in Seattle, sharing how educators are building AI fluency through sideby’s peer-to-peer model. He spoke to the power of conversation, not content, in shaping how schools adapt to emerging technology.

AI is not the Segway

I get it. I’m a critical consumer here even though I am advocating for mass consumption of AI in education. Mass critical consumption. Mass aware and thoughtful consumption. Mass study Joy Buolamwini’s Ted Talk, join The Algorithmic Justice League, learn from this article about the magnitude of bias, apply UNESCO’s AI Competency Framework etc etc etc. Mass led by us for us consumption in education. because it’s not the Segway. (And if you don’t know what the Segway is, perfect.) I’m talking to folks in education, at schools and universities as an insider and outsider, and sometimes it sounds like people are talking about the Segway when they’re talking about AI in education…

Valuing Teachers for more than just the climb

It's like staying in a school, actually teaching and working in a school for years (more than two years if you want to really get down to it), is somehow an indication of your worth in the field of education. Meaning your worth is inversely connected to your years looking at students in the eyes every day…