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 tell us about your role in the edtech and startup space? What unique perspective do you bring to these industries?

I'm Vasilii Kiselev, Legacy Online School's co-founder and CEO. My background is in tech, design, and entrepreneurship—I originally scaled a digital manufacturing startup into a global player before shifting my focus to education.

In EdTech, I'm passionate about how tech can be applied not to substitute teachers, but to enhance the learning experience and make education more human, not less. In digital marketing, I've learned that simplicity and storytelling always trump noise and gimmicks.

I also manage HR along the same lines as product development—build for people, moving fast, and fixating on alignment. Startups are my playground because they compel you to think creatively on tight deadlines and lead with intent over structure. Tying all this together is an unstopping curiosity and believing in innovation as well as that, unless it is tackling real problems for real people, it is no innovation at all.

What was your journey like from your early career to becoming a leader in edtech and digital marketing? Can you share a pivotal moment that shaped your path?

My journey wasn't direct—I started in digital manufacturing, building a startup from the ground up with very little funding. It was a crash course that taught me how to problem-solve on my feet, present ideas clearly, and build systems that would grow.

It wasn't until I saw the inflexibility of traditional education and how little it still catered to students who didn't fit into the "standard" mold that I made the leap into EdTech. I knew that tech could provide something else, something more human.

One such moment came early in Legacy's days, when a parent sent an email saying their child—who had struggled for years in regular brick-and-mortar schools—finally felt seen and capable. That hit me hard. No longer was this a startup; this was a mission. Every subsequent decision—marketing, product, team—was filtered through the lens of impact.

Based on your experience with Legacy Online School, how have you seen the intersection of edtech and digital marketing evolve? Can you share a specific campaign or strategy that yielded unexpected results?

The intersection of EdTech and digital marketing shifted from feature-selling to storytelling. Early on, we focused on tech specs—platforms, tools, curriculum design—but what actually moved people was emotion: parents seeking hope, students wanting a second chance. A surprise campaign for us was a sequence of student video testimonials. Not a lot of production, but genuine stories taken on phones.

Those ads outperformed all of our shiny ads we'd ever produced. Engagement exploded, questions doubled, and it redefined how we interacted with our messaging. Folks don't just want online school—they want to be heard and valued. That campaign showed us that authenticity isn't a tactic; it's a strategy.

You've mentioned the impact of AI in personalized learning. How have you practically implemented this at Legacy Online School, and what challenges did you face in the process?

Here at Legacy, we use AI to customize content delivery and pace based on the best way each student learns—whether they're visual, analytical, or need more time with certain concepts. We designed monitoring systems that track engagement habits and notify us if a student appears lost or bored so we can act before it becomes a problem. It's not cool technology—it's making sure no child slips through the cracks.

The biggest challenge? Making it feel human. Families don't want their child "taught by a machine," so we've worked hard to keep teachers central while AI works quietly in the background, supporting both students and staff. Balancing automation with empathy has been the key—and it's still evolving every day.

As someone who has successfully balanced AI integration with maintaining a human touch, what advice would you give to other edtech startups looking to do the same?

Start with people, not features. Too many EdTech startups approach AI as the product, when in reality it must be the system of support. Ask: How can this tech make the teacher better, not replace them? Here at Legacy, we never introduce AI tools without first considering how they make the human experience better—student relationships, teacher assistance, or trust from the family.

Also, be transparent. Educators and parents are understandably anxious about automation in schools. If you can explain what the AI does—and more importantly, what it doesn't do—you will earn their trust. Don't aim to "disrupt" education. Try to serve it better. That's where the real opportunity resides.

In your experience, how has the rise of micro-learning affected your approach to both education delivery and marketing? Can you share an example of how you've adapted your strategies?

Micro-learning has utterly revolutionized the manner in which we're doing attention and engagement—both inside and outside the classroom—and also advertising. Not only are today's students simply used to short-form content, they expect it. We've reshaped portions of our curriculum at Legacy into bite-sized chunks that can be absorbed in 5–10-minute doses without giving up on depth. It's enabled students to find momentum and achieve a feeling of success faster.

On the marketing side, we've mirrored that approach with short-form video content, micro-campaigns, and quick, value-packed emails. One experiment that worked surprisingly well was a "30-second myth-buster" video series tackling common misconceptions about online learning. It was simple, clear, and incredibly shareable—exactly what today's attention economy responds to.

You've touched on the importance of humanizing automation in your marketing efforts. How does this philosophy extend to your human resources practices within your startup?

Humanizing HR automation is all about leveraging technology to enable relationships, not replace them. At Legacy, we're automating the routine—like scheduling, onboarding paperwork, even first-round candidate screening—so we can spend more time actually meeting people. Culture isn't built in systems; culture is built in conversations.

We also use internal feedback tools powered by AI to determine patterns in team sentiment, but the follow-up is always human. If someone's having a problem, no dashboard will solve that—a real conversation will. The goal is to make each team member feel seen, not watched. As with education, the technology is there to complement the human, not replace them.

Given your success with LinkedIn for personal branding, how do you approach training your team to leverage social media effectively? What's a lesson you've learned the hard way in this area?

I remind my team: "Don't post to impress—post to connect." The finest content is never polished perfection but honest insight. We teach our staff the usage of social media, especially LinkedIn, as a means of establishing credibility and trust by sharing real experiences, lessons learned, and occasionally failure. People connect with people, not brands trying to behave like people.

One hard lesson that I learned early on was that trying to go for virality dilutes your voice. We had done a campaign in the past that had gotten massive engagement—but none of it had translated, because it wasn't true to who we are. Nowadays, we aim for consistency, simplicity, and staying true to mission. Social media is a marathon—and authenticity is your best currency.

Looking ahead, what do you see as the next big challenge at the intersection of edtech, digital marketing, and startup culture? How are you preparing your team and business to meet it?

The next big challenge is navigating the tension between personalization and privacy. As EdTech and digital marketing become more data-driven, the temptation to over-optimize is real—track everything, segment everything, automate everything. But in doing that, we risk crossing the line from helpful to invasive. The question becomes: how do we stay smart without becoming creepy?

At Legacy, we're preparing by baking ethical thinking into our product and marketing decisions. We train our team to see data not just as numbers, but as people—real students, real families. We're also investing in tools that give users more control over their experience, not less. In startup culture, speed is often the default—but the next era will reward thoughtfulness just as much as hustle.