Benjamin Harris: The Mind Behind One of Cybersecurity's Fastest Risers

watchTowr does what the rest of the industry can't or won't. While most security firms hand you a dashboard full of problems and wish you luck, watchTowr shows clients their exact weaknesses and what to prioritise to stay ahead of attackers. In a space drowning in alerts, they actually fix things. It's a posture that has earned watchTowr the trust of Fortune 500 companies and critical infrastructure organisations across the globe.

I sat down with Ben to talk about that move, building from scratch in Southeast Asia, and why the best founders are almost never the ones with the most logical plan.

Lachlan: Let's start at the beginning. What originally made you make the move to Singapore?

Ben: At that point I'd gone straight into what was then called offensive security, specifically cyber consulting. I joined a company called MWR at the time, based out of London. They had taken significant funding and effectively sent an email around saying: “We're opening offices in Dubai, Singapore, and New York, who wants to go?” I must have been 20 and just thought - “yeah, okay, why not?” So I put my hand up for Singapore, and 6 weeks later, I turned up with three suitcases, a hotel room, and was told to figure it out. Which, honestly, is a running theme throughout my life. I stayed for 10 years, so no complaints at all.

Lachlan: I feel like when you make those spontaneous moves, you set your expectations low and don't know what to expect, so in my personal experience almost every outcome ends up being a surprisingly positive one.

Ben: That's fair. And look, I always tell people, probably to their annoyance, just say yes to everything. It forces you to try things you wouldn't logically choose.

Lachlan: So 10 years in Singapore, now split between New York and London. When you move to a new country or market, at what point do you stop feeling like an expat and start feeling like you actually belong?

Ben: Honestly, I'm not sure, and that's a genuinely great question. I think it's when someone asks "where's home?" and you instinctively name that place without having to think about it. New York is not that place for me yet. Singapore definitely had it at one point. Where home actually is right now, I have no idea.

Lachlan: I relate to that. Australia and Singapore are both "home" in different ways, but neither one fully. Personally, I find the switch happens in hindsight. Like, I did my national service in Singapore in 2020 to 2022, didn't really think of it as home at the time. Then did an exchange at NUS at the end of 2024, left, looked back, and it suddenly felt like it. I think it's almost impossible to know you're home while you're living it. 

Lachlan: What does Singapore have that differentiates it from New York and London, personally and for watchTowr?

Ben: The flippant answer is the sun. And honestly, that's more material than it sounds. Waking up to warmth every day genuinely does affect how your day goes. But beyond that, Singapore is wildly efficient. It's built to support business. You have a government that's extremely pro business, supportive of both homegrown startups and large international companies moving in. Being in Singapore during our early days was incredibly helpful, especially now as we continue to scale in markets like New York. 

Lachlan: Yeah, and it's a genuine melting pot of cultures, super internationally connected across Southeast Asia, with a government that actively supports entrepreneurs. A great base before you expand into other markets.

Ben: Absolutely. And I'd do it again without hesitation. Access to organisations, a supportive regulatory environment, engineering talent. Singapore has really positioned itself well as a launchpad.

Lachlan: Going back to when you were younger, there's that well-known story about being asked to leave school. A lot of people would dwell on something like that as a negative, but it seems like you almost used it as fuel. Did that experience drive you toward building something of your own?

Ben: The theme throughout my life has been that I've never really thought too far ahead. In that situation, the potential fallout didn't really hit me until about six months later. I was just kind of, whatever. But what's always driven me is people telling me I can't do something. That genuinely frustrates me in a way that makes me want to prove them wrong. I still remember someone at a Christmas party telling me I'd never earn beyond a certain amount because of X, Y, Z. That just pushed me further. Having my own business was always an idea in the background, more of a pipe dream than a plan. But COVID changed everyone's perspective on what work should look like, and that was definitely the catalyst for me to actually follow through. Everything I've done in my life has been driven by passionate interest, as opposed to logical planning. Which both has its pros and cons.

Lachlan: So COVID was the moment that really solidified the decision?

Ben: The joke I always make is this: I was in consultancy for a long time running and building high end red team operations, breaking into clients over extended periods to simulate real cyber attacks and test their resilience. The consultancy model took all of my hair. So I thought, in my slightly optimistic way, let's get into tech, let's build a product that does the same thing but just focuses on the computers, not the people. Surely that's simpler, surely life will be easier. And of course it wasn't. But yeah, the frustration with how the industry operated, and the belief we could do it better with automation, was the main driver.

Lachlan: You landed your first banking client within two months of starting watchTowr. That's remarkable for enterprise sales, let alone in cybersecurity. How did that happen?

Ben: Cyber is a results driven market. People don't buy into theory, they buy into what you can demonstrably do to help secure them in a tangible way. That, combined with the fact that the team came with a strong existing reputation in the industry, meant that when we said "trust us, give it a shot," it (hopefully) carried weight. We also took a very deliberate approach to making it as frictionless as possible to try us. We don't deploy agents, we don't install hardware or software in your environment. We're fully external, entirely on the internet. We just need permission. So the barrier to entry for a pilot is essentially zero. Credibility plus low friction, and then you just let the outcomes speak for themselves. And that played into Singapore's advantage of opening access to people who can make these things happen.

Lachlan: When you were raising your seed round, what were those early investor conversations like? Were you running those yourself?

Ben: At that stage, it was just me. Talking to investors is a numbers game early on. Speak to as many people as possible, understand what they're focused on, and then work out who's actually a fit for you. Southeast Asia's VC market has historically been very B2C oriented. Grab, Gojek, that world. Not as comfortable with B2B enterprise tech. So it became obvious quite quickly in conversations who would be a good long term partner versus who would struggle with the reality of enterprise sales motions, because you have to plan for the bad days as much as the good ones. The key was identifying that subset of investors who genuinely understood enterprise tech and were willing to back it early. We had an MVP, we had proof the tech worked, we had early pilots, and so we weren't walking in with a deck and asking for cash. Honestly, you feel the click within about two or three minutes of a conversation - it's really obvious.

Lachlan: Were there investors who fundamentally misunderstood what you were building?

Ben: The ones we didn't go with, yes. There was one who suggested that GTM for us was all about Google Ads and Facebook Ads. Which, for enterprise tech, is just completely disconnected from reality. But that's not a criticism of them. They were so focused on B2C that B2B was genuinely difficult for them to engage with. It just wasn't worth forcing that fit. There's also a real challenge in explaining cybersecurity to investors who aren't in the space. If you oversimplify, suddenly everything looks like a competitor. If you go too deep, you lose them in detail. Getting that balance right, communicating what you do and how it's differentiated without losing people, that's an art form. But if they're genuinely interested, they'll put in the effort to understand.

Lachlan: As watchTowr expands into the US and UK, is Singapore still the right headquarters for the business?

Ben: Absolutely, no question. Singapore is still our HQ and there are no plans to change that. We love what Singapore has done for us, and what we can continue to do in the wider region. But as any company grows, focus naturally shifts in different directions at different times. The US is a major priority right now, but Singapore remains critically important. It's more about figuring out where the next stage of exponential, non-linear growth will come from, and capitalising on it quickly. Singapore is very much part of that equation.

Lachlan: There's a lot of noise in the cybersecurity space right now. Everyone's throwing AI on their pitch decks. What actually differentiates watchTowr?

Ben: We are the fastest in the industry to react to emerging threats, which means we're the fastest to tell our clients: this thing just happened, here's whether you're affected, and here's how to fix it. 

We're not saying "good luck, go check." We're saying: here's the situation, here's your exposure, here's what you need to do. 

That's end to end problem solving, not just information delivery. The industry is drowning in data and organizations don't need more of it. They need to know what to do with what they already have. We're focused on actually making clients more secure, not just louder in their inbox. And given that cyber threats and AI are both accelerating rapidly, the speed at which we can identify and respond to what's emerging is what really matters. I'm very proud of that.

Lachlan: Outside of work, what are you secretly really good at, or genuinely obsessed with right now?

Ben: Honestly, nothing. And I know that's a terrible answer. But I just don't have time for anything outside of work right now. That will either pay off or be my downfall. The jury's still out. 

Lachlan: I think it kind of speaks for itself, though. That level of focus is probably what it takes.

Ben: We'll see!

There's a pattern to how Ben Harris operates. Say yes. Figure it out. Move faster than the problem.

It sounds simple. But most people don't actually do it. They wait for the right moment, the right plan, the right market conditions. Ben turned up in Singapore at 20 with three suitcases and no roadmap, and just got to work.

watchTowr has since led research that demonstrated the ability to compromise governments, militaries, space agencies, and supply chains, not maliciously, but to prove a point the industry keeps refusing to hear. That the way we think about cybersecurity is broken. That more data is not the answer. That speed, clarity, and accountability are. 

In a space that sells fear, Ben sells solutions. In a region the world is still learning to take seriously, he built something global that started from a hotel room in Singapore. And he's still just getting started.

The kid they expelled at 17 is now the one telling Fortune 500 companies where they're vulnerable.