CTO Chats with Roy Penn, Chief Technology Officer at Tymely

I’d love for you to give a brief overview of how you got into IT and what your career journey has been to becoming a CTO.

Briefly, I was in Israeli Army intelligence for a few years, and since 2008, I’ve been involved in startups. I was a developer and led development in several startups. I’ve been working in AI for the past 10 years now and working with the cloud for about 14 years. I’m also the founder of an AI startup, which I’ve been running for the past three years.

That must be exciting. I know the industry is evolving really rapidly, and new technologies, such as AI, are obviously shaping that. What are the current challenges you’re facing, and how are you addressing them?

It’s an interesting question. There are a lot of challenges. On one hand, things are moving extremely rapidly with what’s available. AI is becoming more available and well-known, expectations are increasing, and cloud tools are becoming more accessible. The competition between cloud tool providers is very intense. For us, whenever we need to do something, we have to choose the right tools, but it’s becoming harder and harder just to map out what the possibilities are.

On the other hand, expectations from people are very high. I’m sure you’ve interacted with ChatGPT, right? Most people think it can do anything, which creates a gap between expectations and reality. A lot of times, when you present an AI solution to potential customers, they’ll say, “But why can’t it do this?” They might claim they know ChatGPT can do it, and then you’ll have to explain whether or not that’s really possible. It’s a blessing, though. Customers are engaged and pre-engaged because they already know about these technologies. The issue is that when customers have high expectations, there’s a chance to meet them and win the account. But customers without expectations don’t care about what you’re doing—they disengage and never buy. So, it’s a blessing, but it’s easy to lose sight of what’s really possible. For example, people think we should already have flying cars or self-driving cars. It seems so logical that ChatGPT should be able to drive a car by now.

Yeah, it seems like there’s a lot of overestimation of what AI can do and what you can do.

Yes, absolutely. I think that’s a very valid point, but it’s not enough. I gave a talk at a conference about AI a month ago, and I mentioned a moment in 2012 when AI first solved a problem in computer vision. Let me show you the presentation slide.

Go for it.

Can I share my screen with you somehow? Okay, I’ll share my screen now. Can you see this picture? In 2012, AI or machine learning was first able to identify a dog in this picture. Can you see the dog?

Yeah.

It’s right here; this is the dog. The moment AI spotted the dog, news articles all over the world declared, “Autonomous cars are here.” Did you see this? This is an article from 2012. The expectation was that because the major problem was solved, self-driving cars were next. Just because, in 2012, AI could identify a dog, the expectation was that self-driving cars would follow. And so, expectations became extremely intense.

That’s interesting, actually. It also gives you a nice glimpse into where we want our technological development to go. It’s very interesting. I’d never noticed this before. I’ll definitely need to do some research there. I feel like you just opened a gate for me even though I’m not tech. With all this in mind, what do you think is the biggest technological or innovation opportunity for IT leaders in the coming years? What should they focus on right now?

That’s a very broad question. IT leaders span many different verticals. But generally speaking, I’d say it’s not just about the technology or the emerging technology—it’s about the product you’re trying to create. Even if it’s low-tech, people like it and want it, and it solves a problem, that’s great. Sometimes, technologies are double-edged swords. Imagine you have two technologies—one does 80% of what you need, but it’s so new that it’s not extensible. The other does 50%, but it’s more mature and extensible, and you could get it to 95%. You might have to work harder with the latter, but it’s a more proven option.

So, I would advise anyone in IT or the tech industry to be aware of the latest technologies but not rely solely on them, as they may not be mature enough. You have to take into account what you really need. If your core competency relies entirely on someone else’s work—like if your entire product depends on ChatGPT working correctly—then you’re exposing yourself. You have to be careful. It’s important to focus on solving the problem for your customers and building the product around that, not just on the coolest features.

Yeah, I think that’s a recurring theme—how to bridge the gap between tech and business and not let tech run wild without any business case for it. I’m assuming there will be more roles like product management, people who can bridge that gap between tech and business and have that horizontal view of things. But I’d love to hear from you; what do you think is the next big thing in IT in the next three to five years? Obviously, AI is your focus, so that’s an easy answer, but is there something else you’re observing that could cause a major shift?

It’s a good question. First of all, no one ever asks me that, so I can take this in any direction. The history of computer science is really about enabling more people to do more work. If you think about it, in 1972, they created the C programming language, which was a breakthrough because it allowed you to speak with hardware the same way you speak with software. That essentially made it easier for more people to write software. Then, as languages evolved—like C++, Java, Python—it became easier for more people to create software. The same is happening with AI. It’s just another step in that direction, another tool that enables more people to create products.

AI doesn’t remove the need to think about the product, though. I can come up with 10 different products that do the same thing, and one of them will likely be the best. For example, you probably use either an iPhone or an Android phone, right? You don’t use a Windows phone or a Symbian phone. It’s not about features—it’s about the team behind the product understanding what users want. Google didn’t have the most features, but it figured out that people just wanted a simple, effective search engine. Gmail wasn’t the first email service, but it was the best at what it did. It understood what users wanted and executed it well.

In the next few years, I believe more people will be able to create the tools they need, regardless of their field. We’ll see more people in different disciplines—artists, teachers, and others—able to create the tools they need using AI and technology.

Yeah, that’s a great point. It’s like software creation is being democratised. I feel like I’ve seen this in my personal experience. My friends, who know nothing about coding, can pull up websites as if it’s nothing. They barely know what a computer component is.

But that’s wonderful, right? It’s like, who’s going to write the next big novel? Anyone can. A hundred years ago, if you wanted to write a book, you had to find a publisher. Today, you can write it and publish it yourself. And you can reach your audience. The same is true with other disciplines. AI and technology are opening up those opportunities for everyone.

That’s a very valid point. I would love to know—given that the regulatory environment is changing rapidly, and many technological advances are happening, but policymaking is lagging behind, how are IT leaders like yourself navigating these challenges?

There are rules and regulations you must adhere to, and then there are things you should do because they’re morally correct or good for your business. And sometimes, there are things you do simply because if you don’t, people will frown upon you. For example, there was a company that used facial recognition to predict whether someone would repay a loan, but it was extremely racist and offensive. I hope they’ve gone bankrupt by now. The point is there were no regulations around it at the time. It’s up to people, as consumers, not to buy products they don’t agree with. Most good decisions come from the bottom up, not the top down. Politicians may not always be the ones to lead the charge on AI policy, and we just have to manage it ourselves.

In a word, what do you think is the most critical skill for IT leaders today?

It’s grit. It’s the ability to keep going, to face failure, and try again. Short and to the point.