We sat down with Shailesh Hegde, the CEO of Hubilo, to talk about his journey from engineer to CEO, the challenges of pivoting a business during the pandemic, and how he’s helping Hubilo reshape the webinar space. Shailesh also shares practical advice for techies thinking about entrepreneurship and insights on building a strong product mindset in teams.

Let’s start with your story. How did your career evolve, and how did Hubilo fit into the picture?
Shailesh: My career has been quite a ride. I started as a QA engineer, where I discovered I wasn’t great at writing code but excelled at figuring out how systems break. That skill kept me in QA for nearly a decade until I realized I wanted to do more.In 2016, I transitioned into product management at BlueJeans, a move that felt like finding my calling.
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I loved understanding the “why” behind every feature and how it solved customer problems.

Hubilo came into my life during the pandemic. It was a big shift for me stepping into a CEO role for a company that was navigating massive challenges. It’s been a rollercoaster, but the journey has taught me so much.

Q: Hubilo went through a big pivot during COVID. What led to that decision, and how did you pull it off?
Shailesh: The pivot was driven by numbers and market realities. We saw the webinar space as a huge opportunity, but we needed to build something modern something that could outshine the outdated tools customers were stuck with.We started with deep research. My team analyzed competitors and spoke to over 50 potential customers to uncover their pain points.

That’s how we identified what I call “swapper features” the must-have elements that would make people leave their current platforms for ours.Once we had a clear direction, we aligned the team and built a simplified webinar platform. It wasn’t easy, but the results have been worth it.

Q: Balancing customer feedback with innovation is tough. How do you handle this at Hubilo?
Shailesh: It’s a delicate balance. At BlueJeans, we focused too much on existing customer requests, which held us back from innovating. At Hubilo, in the early days, we did the opposite we built features on instinct without enough validation.Now, we focus on combining customer feedback with a long-term vision. It’s about having honest conversations with the team, what are we optimizing for right now, and how does it fit into our big-picture goals? There’s no perfect formula, but clarity and alignment go a long way.

Q: What’s your definition of a “product mindset,” and how do you build it in your team?
Shailesh: For me, a product mindset is all about asking the right questions. Why are we building this? Who is it for? What problem are we solving?I encourage everyone on my team, especially engineers, to challenge decisions and dig into the “why.” When you have that mindset across engineering, design, and product teams, you end up building things that actually make a difference.

Q: You transitioned from a tech role to leading the business. What was that like?
Shailesh: It was a huge shift. As engineers, we don’t always realize how tough sales and marketing are until we’re in the trenches with those teams. Watching them execute taught me a lot about collaboration and respecting other roles.

One of my biggest learnings was understanding when to involve others in decision-making. Some decisions need a lot of input, while others don’t. Striking that balance is key.Respecting and learning from your sales team is another big one. Tools like Gong and Fireflies make it easier to listen to sales calls, and I encourage my product team to do that regularly. It’s a goldmine for understanding customers.

Q: Let’s talk about technical debt. How do you decide when it’s worth prioritizing?
Shailesh: I see tech debt as part of the roadmap, it’s not a separate bucket.If a tech debt issue is blocking a major feature or causing customer pain, it’s an easy decision to prioritize it. For example, if fixing tech debt now will help us deliver a critical feature in six months, we do it.The key is linking tech debt to business goals. A list of tech debt on its own doesn’t help anyone. When you tie it to the roadmap, it becomes clear what needs to be addressed and why.

Q: Any advice for engineers transitioning into entrepreneurship?
Shailesh: Get really good at customer discovery. As engineers, we’re great at building things, but understanding what to build is a different skill.Books like The Mom Test and Continuous Discovery Habits are fantastic resources.

They teach you how to ask the right questions and uncover what customers truly need.Doing this groundwork also helps when you hire your first marketers or salespeople. If you can give them clear insights, they can hit the ground running and scale your product faster.

Q: You come across as calm and collected. How do you stay balanced as a leader?
Shailesh: Experience helps. Over time, you learn to focus on solving problems instead of reacting emotionally.That said, staying calm doesn’t mean there’s nothing going on inside.

There’s always a lot running through my mind about how to hit our goals and solve challenges.Having a motivated team also makes a huge difference. I believe motivation has to come from within, you can’t create it for someone. My job is to align the team and give them the clarity they need to do their best work.

Closing Thoughts
Shailesh's journey from QA engineer to CEO is a masterclass in adaptability and customer focus. His advice to aspiring entrepreneurs and his approach to leadership offer valuable lessons for anyone looking to build products or businesses in today’s fast-paced world.

‍“The key is to keep learning and growing every day. That’s how you stay ahead and keep making an impact.”
- Shailesh H.