Small Biz Leader · July 15, 2025
This interview is with Vasilii Kiselev, CEO & Co-Founder at Legacy Online School.
Vasilii Kiselev, CEO & Co-Founder, Legacy Online School
Can you introduce yourself and share your expertise in EdTech, Human Resources, Digital Marketing, Startups, and Parenting?
I'm Vasilii Kiselev, the co-founder and CEO of Legacy Online School. My experience lies in EdTech, startups, and digital marketing—each of which shapes my vision for building our school. I'm about creating personalized, flexible learning that combines forward-thinking technology with authentic human support. As a parent myself, I know firsthand how hard it is for families to find the right educational path. That empathy drives our mission to make quality online education accessible and supportive. I also just so happen to believe that storytelling and authentic connection matter most in marketing and that a mission-driven team is the biggest secret to success. Legacy is more than a company to me—it's a community where tech and heart intersect to revolutionize learning.
What was your journey like in becoming a leader in these diverse fields, and how do they interconnect in your work?
My journey has not been linear—it's been curiosity, experimentation, and sheer love of solving real problems. Starting in digital marketing and start-ups gave me a high-velocity background where adaptability was the only currency that mattered. Diving into EdTech added deeper layers—knowing people and how they learn became most important. Parenting brought it home, getting first-hand experience of what families truly need from schools.
These domains intersect in my work by keeping the focus on people—students, parents, and teachers—while leveraging technology and strategy to create meaningful, personalized learning experiences. It's a mix of hustle and heart that drives everything we do at Legacy.
Based on your experience with Legacy Online School, how has the integration of AI in education changed the way you approach personalized learning?
AI has brought much more personalized learning at Legacy Online School. It enables us to transcend one-size-fits-all approaches by observing every student's strengths, challenges, and learning pace in real time. Using AI, we can dynamically tailor lessons and support to meet the needs of each student, making education truly student-centered. But it is not about replacing human interaction—AI enables our Personal Learning Support Specialists and teachers by giving them wiser tools to do what is most important: mentor and inspire students. This marriage of tech and human touch is revolutionizing how we enable every learner to thrive.
Can you share a specific challenge you faced when launching your EdTech startup and how you overcame it?
A big challenge we faced in opening Legacy Online School was building trust within a market that is skeptical about online education. People want to know that their kids will get a sound, accredited education—not just worksheets on a screen. We solved this by focusing on transparency and relationships: publishing real student testimonials, offering real-time support with Personal Learning Specialists, and earning highly respected accreditations and awards. It wasn't abrupt, but developing that human connection along with technology helped us break through the cynicism and grow.
How do you balance the use of technology in education with the need for human connection, especially in the context of parenting and child development?
Balancing technology and human connection is really about putting people first. At Legacy Online School, we use technology to personalize learning and make education flexible, but we never want it to replace the relationships that matter most. Our Personal Learning Specialists and teachers are there to guide, encourage, and connect with students and parents every step of the way. From a parenting perspective, kids need that emotional support and real-world interaction to thrive. So, technology is a powerful tool—but it's the human connection around it that truly makes learning meaningful and impactful.
As someone involved in both education and HR, how do you see the future of workforce development changing, especially with the rise of remote work and online learning?
The future of workforce development is indeed evolving with remote work and online education becoming the new reality. I foresee emphasis on lifelong, flexible learning—people will need to constantly upskill and reskill in cycles that fit their lives, not the traditional classroom setting. HR and education will need to partner closely to create bespoke learning journeys that align with real job skills and career goals. At Legacy, we're already thinking beyond K–12, exploring how to prepare students not just academically but for a world where remote collaboration and digital skills are essential. The key will be blending technology with meaningful human guidance to help people adapt and thrive in an ever-changing work landscape.
What's the most unexpected lesson you've learned about parenting through your work in EdTech, and how has it influenced your approach to developing educational technology?
I've learned just how much parenting is about patience and flexibility—not just for parents, but for educators and technology too. Kids don't learn in a straight line, and families face unique challenges every day. This has influenced our approach at Legacy to build technology that's adaptable and supportive, not rigid. We focus on creating tools that empower parents and students to take control of their learning journey at their own pace, with human support always just a click away. It's taught me that EdTech has to meet families where they are, with empathy and real-world understanding.
Looking ahead, what do you believe will be the next big innovation in EdTech, and how can startups in this space prepare to meet future challenges and opportunities?
I think the next trend won't just be smarter AI or better data—it will also be about crafting learning that feels human. Imagine systems that monitor not just grades or milestones, but notice a student's mood, motivation, and energy levels and adapt lessons in the moment to engage, intrigue, and sustain them. This emotionally aware technology can enable learners to feel witnessed and cared for, not just taught.
For startups, it means shifting away from the development of static tools to building dynamic, malleable ecosystems that grow alongside each student's unique trajectory. It's about embracing the risk of learning—the missteps, the aha moments, the moments of doubt—and using that to fuel larger growth.
The future is for those who envision beyond content delivery and personalization as a checkbox, and instead design living, breathing learning experiences to grow every learner's potential regardless of how they learn and where they come from. That kind of visionary, compassionate innovation will redefine education for generations to come.