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5 ISTELive 26 takeaways: Fixing the broken line between schools and families
I got asked a version of the same question a dozen times at ISTE this year: why would someone who spent 16 years working inside school districts end up building a parent communication product? The honest answer is that I lived the problem long before I thought about solving it.
I’m the parent of two high schoolers, and even after a career in edtech, I could not keep my own kids’ school communication straight. An email here, a text there, and in one of my kids’ districts, actual updates going out over WhatsApp. It was genuinely confusing, and I say that as someone who is supposed to be good at this. When I first talked with the ParentSquare team, what got me wasn’t a pitch; it was realizing the fix already existed: one simple channel instead of five different ones. Joining felt less like a career move and more like fixing my own life. Here’s what I kept coming back to in conversations at ISTELive 26.
- More channels made things worse, not better. The instinct in school communication has always been to add another tool: another portal, another app, another push notification. My own experience argues the opposite. Stacking channels doesn’t raise the odds a parent sees what matters. It just multiplies the places they have to check.
- AI’s job is to answer “what do I do with this,” not to make another chart. I spent years building reporting dashboards before ParentSquare, and I’m candid about the lesson I took from it. I created more charts, more graphs, more tables, more pages of reports, and not once did anyone get excited about a new graph or chart. What people actually wanted was the next step. That’s the shift I think AI is supposed to drive, from “here’s the information” to “here’s what you can do about it.”
- Conversation starters turn a shrug into an actual conversation. The example I gave a few times at ISTE: instead of a parent asking “what did you do at school today?” and getting “nothing,” ParentSquare’s AI turns a routine update into something more specific, like “so-and-so visited today and you had this assembly, what did that teach you about responsibility?” Small idea, universal problem. We’re expanding it to cover attendance, academics, events, and the school calendar.
- Contactability matters more than message volume. Across our schools and districts, we’re at a 99.4 percent contactability rate, and that’s the foundation everything else is built on. If only 70 percent of a school’s parents were actually engaging with a messaging system, I wouldn’t trust it for anything important. Built on top of that is Attendance Plus, which sends personalized, encouraging messages when a student misses school rather than a flat alert. A student coming back after being sick gets something like “we’re so happy she’s coming back to school” instead of just a data point.
- Privacy needs specifics, not reassurance. When people ask whether student data stays inside our walled garden, I don’t think a vague answer is good enough. ParentSquare is FERPA-and-COPPA certified. We de-identify all data that goes to any model, and we never use family data to train anything. That’s the level of detail I think every district should expect from any AI vendor, not just us.
One more thing worth mentioning
The same AI is built for school staff too, not to replace them but to help them. It can rewrite a rushed, three-paragraph text into something clearer, or flag a better channel to cut down on messaging fatigue. The goal is guardrails built on real experience and data about what actually works, not automation for its own sake.
I dug deeper into all of this with the EduTech Guys at ISTELive 26: why schools end up drowning in disconnected channels, and how AI can turn school updates into next steps that help families stay involved. If these takeaways resonated, the conversation is worth a listen.