Growth, AI and Leadership in Product: Simon’s journey at Preply

A company in hypergrowth is always in motion — teams are shifting, priorities are evolving, and product roadmaps are never set in stone. Navigating that environment isn’t just about having experience — it’s about being able to adapt.

That’s exactly what Simon has done at Preply. Since joining as Product Director, he’s played a key role in shaping the company’s approach to product strategy, hiring, and AI adoption. Now, as VP of Product, he’s leading a team that’s redefining how Preply builds for scale. Here, he shares his insights on product leadership, decision-making, and the realities of growing a product team in an industry that never stands still.

Simon, you joined Preply from a much larger company. What motivated your move, and how has the transition to a scale-up environment shaped your approach to product management?

I joined Preply in July 2021 after eight years at an online travel agency in Bangkok. Initially, I wasn’t planning on leaving — I even referred someone else for the role! But after several conversations with the team, I became really excited about Preply’s mission, the caliber of people, and the way they think. A few months later, I packed up and moved halfway across the world.

Coming from a well-established company, I noticed key differences right away. Both companies were data-driven and full of high-caliber talent, but Preply’s approach was much more customer-centric. Unlike a travel business, where success is measured in short-term conversions, Preply’s product is built on long-term learning relationships. This required a shift in my thinking. I had to unlearn my previous mindset and embrace a more holistic view of product success.

The scale-up environment also meant more chaos, but in the best way possible. There was room to shape how we worked, from prioritization to how we used data to make decisions. I found opportunities to improve structure while staying agile, and I quickly realized that success here meant balancing speed with long-term impact.

One of the pivotal moments in my time here was my first performance review, where the Chief Product Officer, Josh Crossick, said, “There’s more than one way to do product.” That stuck with me. At my previous company, the focus was on price and conversion, whereas at Preply, the product is built on human relationships and long-term learning goals. That meant rethinking how I approached things.

I started off leading the learning experience team, then moved on to work on B2C growth and B2B products. Over the last three years, together with the Product Leadership team, we have interviewed and hired most of the great talent who constitute our product team today. Growing and shaping the team has been one of the most rewarding aspects of my time here.

Part of the fantastic team of Product Managers at Preply 🚀

AI’s Role in Product Development at Preply

How is AI shaping the way Preply builds products, and what’s your perspective on how AI should be integrated into product management?

We’re in a fascinating moment where AI is evolving at an incredible pace, and it’s fundamentally changing how learners connect with tutors and engage with language learning. Preply has a huge advantage because we have the largest repository of real-world language-learning interactions — rich, meaningful data that goes beyond textbooks.

One of the toughest challenges we’re solving at Preply is finding the perfect match between learners and tutors. Unlike traditional e-commerce, where structured data drives decisions, learning is deeply human, shaped by emotions, communication, and that hard-to-define ‘vibe.’

AI is incredibly powerful in helping us make better matches, but we have to be thoughtful about how we use it. It’s easy to get caught up in AI hype, but not every problem should be solved with AI. Instead, we focus on using AI where it genuinely adds value — whether that’s improving tutor recommendations, enhancing personalization, or making learning more adaptive.

What excites me most? AI is lowering tech barriers, meaning the real winners won’t just be those with the best models but those building great products that solve real problems. And that’s exactly what we aim to do at Preply.

High-Performing Culture in Product

Preply has a strong performance-driven culture in product. What does that look like day to day?

One of the most rewarding aspects of working at Preply is the high-performance culture within the product team. Preply’s team is ambitious, fast-moving, and deeply committed to user outcomes. But high performance doesn’t mean burnout, it means clarity in decision-making, accountability, and a focus on impact.

Some of the ways we maintain this culture:

• Ownership mindset — Everyone in product operates with a strong sense of ownership, challenging the status quo and driving change.
• Data meets intuition — We balance qualitative and quantitative insights, making decisions based on both numbers and real user experiences.
• Collaboration over silos — We work closely across functions — marketing, research, data, supply, and engineering to ensure our solutions are holistic and effective.
• Continuous learning — High performers are always evolving. We encourage experimentation, reflection, and learning from failures as much as successes.

Leadership in Product Management

You’ve built and scaled the product team significantly. What lessons have you learned about leadership in product management?

I always feel a bit uncomfortable with this term “leader”. I am constantly learning how to be better at what I do, but I can share a few learnings that I’ve had in my time here. Leadership in product isn’t about having all the answers, it’s about creating the conditions for great products to emerge. Over the years, I’ve learned a few key lessons:

1. Build a shared vision, then get out of the way — Early in my career, I was more top-down. Now, I focus on setting direction and enabling teams to take ownership. The best ideas come from those closest to the problem.
2. Know and share the ‘why’ behind every decision — Being wrong is okay, but not having a rationale isn’t. Clear decision-making, anchored in user and business impact, is critical.
3. Set decision criteria upfront — Avoiding endless debates by defining what success looks like before diving in keeps things moving efficiently.
4. Stay close to the work — Even in leadership, I like to remain hands-on — leading special projects, covering for team members when needed, and staying deeply engaged with the product.
5. Prioritize real impact over optics — It’s easy to get caught up in internal politics, but the best product decisions are always rooted in user and business value.

Advice for Aspiring Product Leaders

What advice would you give to those aspiring to leadership roles in product management?

First, be sure it’s truly what you want. Leadership isn’t the only path to impact. Some of the best product minds are senior ICs who deeply influence strategy without managing teams.

Second, don’t chase the title — focus on driving meaningful impact. The best way to grow into leadership is to consistently own and solve big problems. If you operate with high ownership, take initiative beyond your immediate scope, and drive real change, leadership opportunities will find you.

Finally, remember that leadership isn’t about authority; it’s about enabling others to do their best work. The most effective product leaders create clarity, empower their teams, and keep the focus on what truly matters — building great products that solve real problems.

Inspired by the growth of Simon at Preply? If you’re driven by going the extra mile to raise the bar, hungry to have a visible impact on the business, and would like to join a fast-paced company where growth and learning go hand in hand, then check out our open positions here.