Raviv Ventura is a technology entrepreneur, software engineer, business consultant, real estate investor, and tech writer
Curator’s Note: Raviv Ventura is a technology entrepreneur and software engineer with over 20 years of experience. In an interview series, he shares insights into his journey, emphasizing the importance of connecting technology with business challenges. As co-founder and CTO of PlanToIt, he tackles decision-making problems in the food sector, using AI to translate demand signals into actionable choices. Raviv’s approach to writing on Medium reflects his engineering thoughts and experiences, aiming for honesty and clarity. He values reader feedback and shares lessons from both successes and failures, continually focusing on customer needs in product development and entrepreneurship. This interview was conducted by Dr Mehmet Yildiz, owner and chief editor of ILLUMINATION Integrated publications on Medium, Substack, Patreon, and Digitalmehmet.
Technology Leadership Case Studies Series
Dear Subscribers and community members,
Today I will share a new interview I conducted with a community member. As part of my ongoing interview series with writers and leaders in their profession, in today’s episode, I invited Raviv Ventura to introduce himself, his business and technical skills, and give us insights from his two decades of entrepreneurial work in software engineering. Raviv is a new writer on Medium, but he is not new to writing as an excellent executive-level communicator. I believe Raviv’s technical and entrepreneurial background can be a source of inspiration for aspiring technologists and company founders. I decided to publish this story on Technology Hits to inspire our tech writers and readers.
Hi Raviv, Welcome. Let’s start with a bit about your background.
Hi Dr Yildiz, thank you for the opportunity. As you know, I come from a technical and business background. Currently, I work as a software engineer and entrepreneur with more than 20 years of experience building software products and complex systems.
After completing my computer science degree in the early 2000s, I started my career developing large logistics systems serving hundreds of customers. Over the years, I’ve worked across software engineering, product development, and technical leadership, always enjoying the challenge of connecting technology with real business problems. While working full-time, I also completed an MBA degree to gain business, leadership, and entrepreneurial skills.
I am the co-founder and CTO of PlanToIt. It is not the first company I helped build. Before that, I co-founded and led a startup focused on marketing technology, where I experienced every stage of building a company, from turning an idea into a product and hiring employees to finding customers and dealing with product changes, mistakes, and unexpected challenges.
Those business and technical experiences taught me that technology can work well, but products still need to change because they are not solving the problem customers actually have. That is what brought me to PlanToIt.
I became interested in one of the most challenging operational problems in food businesses: helping organizations make better decisions while demand is still changing and there is still time to influence the outcome. The technical challenge isn’t simply forecasting demand. It’s turning short-term demand signals into decisions that support day-to-day operations before opportunities are lost.
Now, as Co-Founder and CTO of PlanToIt, I lead the platform architecture and product development, turning data and AI models into software that helps organizations make better operational decisions. I am bilingual in English and Hebrew.
Outside of work, I’m married and the father of two children, living in Tel Aviv, Israel. Spending time with my family helps me step away from work, keep things in perspective, and return with more energy. Building a company takes years, so I think it is important to make room for both work and family throughout that process.
What were the key skills distinguishing you in your field?
This is a great question, Dr Yildiz. Apart from hands-on coding in languages such as Python, Node.JS, JavaScript, and more, the critical skills for me were infrastructure building, technical leadership, engineering, team management, strategic planning, entrepreneurship, complex problem solving, negotiation, executive communication, and presentation skills.
Why did you choose your profession?
I’ve been interested in computers and information technology since I was young. While I played computer games, I also spent a lot of time trying to understand what the computer was doing and how the software worked. I spent a lot of time changing things on the computer just to see what would happen. When something stopped working, I tried to understand why.
Later, software engineering became my profession. I liked the work because I could start with a specific problem and build a working product around it. Seeing someone use what I had built was always more interesting to me than the code by itself.
As I gained experience, I became involved in product decisions as well as technical ones. Customer conversations became a larger part of my work. I wanted to hear directly what they were doing with the product and where it was falling short. That gradually moved my work toward product development and entrepreneurship.
Engineering and entrepreneurship are closely connected for me. For example, engineering gives me the ability to build the product, while entrepreneurship requires me to decide what should be built and why. The combination of those two areas has kept the work interesting for me for over two decades, and I am keen to continue.
What are your hobbies, or what excites or entertains you?
I enjoy traveling abroad with my family, finding restaurants we have not tried before, and going on cruises. I like surprises in life such as arriving somewhere new without already knowing what we will find there. As a people person valuing relationships, travel also gives me a chance to meet people and see places and cultures that are different from what I know at home. Most of all, I enjoy having that time with my family.
Now, let’s talk about your writing. Why do you write on Medium?
For me, writing is an extension of my engineering work. Some of the problems I work on take time to understand. Writing them down helps me see where my explanation is unclear or where I may have made an assumption too quickly.
I recently joined this platform because on Medium, I can describe a technical decision in more detail than I can inside the product or the code. I usually begin with something that happened during development and explain how I dealt with it. Writing often forces me to look at the software again and reconsider parts of my reasoning. Readers sometimes raise questions or describe situations I had not thought about.
I enjoy reading people who work in areas different from mine because they usually approach the same problem from another direction. The comments and discussions are useful because they test whether an idea is clear and whether it makes sense outside my own work. I do not publish because I think I have a final answer. I publish because explaining an idea often reveals what I still need to understand.
What are your values as a writer?
The most important value in my writing is honesty. I try to write about what I’ve actually experienced, not just what I’ve read or what sounds convincing in theory. Everything I publish is influenced by years of building products, founding companies, working with customers, leading development teams, and making decisions under uncertainty.
That also means I’m comfortable writing about things that didn’t work. I’ve worked on products, technical decisions, and ideas that looked promising but failed once people started using them. Looking back at those experiences has usually been more useful than writing only about the projects that succeeded. They taught me to pay closer attention to customers and to change direction when something clearly wasn’t working.
Most public stories about startups begin after something has gone well. People hear about funding, growth, or a successful launch, but much less about the months of trial and error before that. I think those earlier stages are worth discussing because they explain how decisions were made and why some of them turned out to be wrong.
I try to write as clearly as I can and avoid making technology sound more capable than it really is. If I describe a problem or an idea, I want it to come from something I’ve actually worked on. Readers can decide for themselves whether they agree with my conclusions.
Do you have any advice for new writers or software engineers?
I can’t give advice to anyone, as we are all different. However, in both writing and engineering, focusing on the customer needs and solving their problems can be the key distinguishing factor in business. In both professions, honesty, integrity, and clear communication are key.
What are your top five stories that you want to share with your audience and why?
It’s difficult to choose only five because many of the articles build on each other, but these are the ones I’d recommend to someone who wants to understand how my thinking has evolved over the last few years.
The first is Break on Through to the Other Side of Planning Architecture Under Volatility. I like it because it shifts the discussion away from forecasting accuracy and toward the architecture behind operational decision-making under uncertainty. It captures the engineering problem that motivated much of my recent work.
The second is Why SKU Level Forecasting Under Volatility Is a System Design Problem. It explains why I believe the real challenge isn’t simply producing better forecasts, but designing systems that help people make better operational decisions while conditions are still changing.
I’d also include Observing the Food System, One Ingredient at a Time. Working with Liat Portal on that project exposed me to a much broader perspective on food systems and reinforced how closely technology needs to stay connected to operational reality rather than theoretical models.
The fourth is Why Forecasting Failures in Food Are Structural, Not Accidental. It explains why many planning failures originate in the design of the overall system rather than in forecasting models alone, and why solving them requires thinking across the entire operational process.
Finally, I’d recommend reading Authority Drift. Although it isn’t about forecasting, I think it raises an important question that applies to every decision-support system. As AI becomes part of everyday operational decisions, people need to understand when to trust recommendations and when changing conditions require them to question, adapt, and make their own judgments. I believe good software should strengthen human decision-making, not replace it.
What are your plans as a writer or as a professional?
I write about problems because I want to know whether other people see them in the same way and whether they have faced them before. Supply chain problems are not new, and many people have already tried to solve them. Their feedback helps me learn from what worked, what failed, and what I may be missing.
Professionally, I plan to continue building PlanToIt and working on the engineering problems behind it. One of the main challenges is taking demand signals that change every day and turning them into clear decisions about ordering, inventory, production, and replenishment. The software needs to give people information they can understand and act on while there is still time to change the outcome.
I also hope to continue contributing to the broader conversation around planning architecture by sharing lessons from real product development and real operational challenges. Some ideas will become technical articles, while others will find their way into the product itself. For me, writing and engineering are closely connected.
Many of the ideas I write about eventually end up in the software. Sometimes writing exposes a flaw in my thinking before I build anything. Other times, I discover the real problem only after I start implementing it.
Thank you for this great opportunity, Dr Yildiz. I will continue to contribute to your platforms and engage in the works of your great community on Medium and elsewhere.
Many thanks to Raviv for giving a glimpse of his interesting life. You can follow him on Medium and connect with him on LinkedIn, Facebook, and ILLUMINATION Slack Workspace.
I also post links to these interviews on LinkedIn to increase visibility for creators, so please consider engaging with this post on that professional platform to grow your audience. Originally published on my author platform.
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