Anupama Vaid is the Founder and President of ParentSquare, the trusted leader in school-home communications, helping K-12 districts nationwide achieve 100% family contactability with an award-winning, all-in-one engagement platform.
1. Tell us about your company and the problem it solves, or its benefit to learners or educators.
At ParentSquare, we help schools engage families to support student success. The platform goes beyond one-way communication—it focuses on building relationships. That means enabling two-way dialogue that includes every family, not just the ones who are already engaged.
If you look at the research, it shows that up to 60% of the variance in student test scores comes from home-related factors. Schools can’t address this on their own. We need to think of student success as a three-legged stool made up of the school, the students, and also the parents. Each leg depends on the others for balance and stability. If one is missing or weakened, the entire structure becomes unstable. That’s why meaningful family engagement isn’t just a nice-to-have, it’s vital. ParentSquare helps schools strengthen that structure by activating the power of families and positioning them as true partners in their child’s education.
We’re more than just a communication tool—we provide the full family engagement infrastructure. This includes everything from two-way messaging to forms, payments, permission slips, and even websites.
Together, these tools help districts unify how they communicate, connect, and build relationships with the community and every family.
2. Where did the idea come from to create your company?
ParentSquare grew out of my own need as a parent. When my daughter started kindergarten, I realized how tough it was to manage all the information coming from her school while juggling work and family life. Teachers were using email, the PTA was using services like Google Groups, the school office was making robocalls, and the principal was sending out a newsletter. It was chaotic. I remember thinking, “Why isn’t this communication all on one platform?”
This was about fifteen years ago, around the time Facebook was emerging as a social platform. People were using it to stay connected in real time and I wanted that same kind of connection with my daughter’s teacher. So, my goal was really twofold: unify school communication, and create a bridge between parents and teachers—especially working parents who couldn’t be at school pickup every day.
I brought the idea to my daughter’s principal and she was immediately supportive. But, of course, building something is one thing; bringing it into schools is another. Those first few years were focused on learning how to sell to schools and meet their unique needs. But once educators began using ParentSquare and seeing its impact, word quickly spread across the K-12 community—it was really incredible.
3. Tell us about one challenge and how you overcame that challenge.
One of our biggest early challenges was ensuring families who weren’t tech-savvy or who didn’t speak English were able to be involved in their child’s education through ParentSquare.
At first, some teachers were hesitant to use our platform because at the time it didn’t reach all parents. That was a big wake-up call for us. I started spending a lot of time going to school and district English Language Acquisition committee meetings and asking families directly: “What do you need? How can we help?”
What I learned changed everything.
Some parents didn’t know how to create a login to their account or weren’t familiar with email—things many of us take for granted—and they needed extra support. Knowing this, we made texting the default since nearly everyone can receive a simple text message. Every message includes a personalized link, and when a parent clicks it, we already know who they are. They don’t need to log in to access the information. That small change made a huge difference in accessibility.
We also introduced automatic language translation—but with extra care. Before translating, we convert the message into plain language to ensure clarity. We also include the original English version so families can ask their child for help if needed. These thoughtful touches came directly from listening to families and understanding their lived experiences.
All of this helped make ParentSquare inclusive by design—not just in features, but in philosophy. Our goal has always been to remove barriers to effective communication and make it easy for every family to feel connected, regardless of their language, digital literacy, or the device they use.
4. What are you most proud of, or what is your company’s greatest achievement?
What I’m most proud of isn’t a product feature or a milestone. It’s the real, human stories we hear from the schools we serve.
One story has stayed with me for a long time. A school administrator told me how she used ParentSquare to send out a volunteer request. A Spanish-speaking family who had never previously been involved responded. They signed up to update the school marquee each week.
On the first day, the administrator saw the mother out there changing the letters with tears running down her cheeks and her son holding the ladder steady below. She told me, “In that moment, I realized I may have just changed the trajectory for that child.” And it was all because the school could invite that mother, in her home language, and provide a way to be involved and be a part of her son’s schooling.
That’s what it’s all about: creating moments where families feel seen, empowered, and part of something bigger than themselves.
ParentSquare gives families a way to participate meaningfully in their child’s education, not just by receiving information, but by being part of the conversation. And on the other side, it lifts up educators, too. We often hear administrators say, “You make us look like rock stars in our community.”
Even veteran teachers who once felt hesitant about technology are using ParentSquare with confidence because it’s that intuitive, flexible, and easy to use. We’re helping schools bridge gaps that once felt too wide, and in doing so, it’s strengthening the support system around every student.
5. Where do you see your company in five years?
That’s a tough one, honestly, because we take a very incremental approach to everything. We’re constantly listening to our customers, learning what they need, and evolving based on what will truly make their lives and jobs easier—not just what’s shiny or new.
With the rapid pace of innovation, especially in AI, it’s hard to say where we’ll be in five months, let alone five years. But we do see incredible potential in using AI to help educators and administrators work more efficiently, so they can spend more time where it matters most: with students.
Imagine a teacher finishing a lesson and receiving a gentle prompt: “Would you like to send a quick summary of today’s lesson to families?” The possibilities for enhancing school-to-home communication are endless.
At the same time, we want to be very intentional about how we integrate AI into ParentSquare because we believe technology should strengthen human connections, not replace them.
But one thing I know for sure is that whatever innovations we introduce, our mission will remain the same: to connect schools and families in meaningful ways that deepen engagement and support every student’s success.
