The Soft Skills Wave Is Here (And Most Aren’t Surfing Yet): Re-Skilling.AI’s Juan Pablo Delacroix Exposes an Unseen Gap

Thank you for sharing your incredibly valuable experience, Juan Pablo. This is an interview I’ve been wanting to do for a while, and I sincerely appreciate you accepting the invitation.

Laureano, please, it’s my pleasure. Thank you for inviting me, and it’s great to reconnect after so many years. We’ve known each other for a long time, so it’s a true pleasure for me.

‍‍Excellent. Let’s start, Juan Pablo, with a bit about your early professional history. Can you take us through your journey into EdTech and your current role?

Even before finishing high school, I started working in my father’s software company, which provided ERP solutions in Argentina. My first experience in technology came during the summers of 1993 and 1994, and I’ve been drawn to it ever since. Early on, it was hard to explain to others, including family, what I was doing—many assumed I was fixing computers or printers!

I’ve worked with various companies, starting in my father’s business and then moving to Sonda, a Chilean firm operating in Argentina, where I sold CAD solutions for industries like architecture and engineering. Later, I spent nearly five years at Oracle, where I learned to navigate complex corporate processes, from sales and pre-sales to multimillion-dollar negotiations. This role also deepened my understanding of critical business areas like HR, supply chain, and finance.

After Oracle, I joined SuccessFactors, later acquired by SAP, focusing on HR solutions and working closely with HR VPs. This role helped me map out how challenges in HR, supply chain, and other areas intersect with financial outcomes.

A turning point came when my mentor and friend, Martín Moreno, invited me to join Blackboard. It was my first experience with a multinational company in the higher education sector—an entirely new challenge. It was both enriching and rewarding. I learned extensively about the education industry, built strong relationships, and met inspiring people shaping future talent.

In 2014, we were part of a movement helping universities navigate the transition from on-site education to hybrid and online models. While today this shift is widely accepted, back then it required significant explanation. I recall conversations with university leaders who prioritized building physical spaces over investing in technology. It reminded me of challenges I’d faced in other industries—advocating for forward-looking technologies with organizations not yet ready to adopt them.

Working in EdTech felt like being part of something far greater than myself—bringing value to a vital pillar of society.

Your background in implementing complex systems in other industries must have been very helpful in connecting business perspectives with education leaders. Many of them are just now being forced to articulate their operations more like businesses.

That’s a spot-on observation, Laureano. My first impression was that higher education lagged behind other industries—like consumer goods, banking, retail, or logistics—where adopting new technology is critical to staying competitive. In those industries, slow adoption means getting left behind.

In higher education, leaders often relied on their institution’s brand and history, confident that students would enroll regardless of technological investments. Families already valued the degree. However, that’s changing as more leaders recognize the industry’s rapid evolution and the need for significant transformation to stay competitive.

To sum up my journey: after five years at Blackboard, I worked extensively with Laureate Education, one of the largest and most innovative higher education networks. Laureate exposed me to forward-thinking teams focused on anticipating the next five to ten years. Projects moved quickly, professionalism was high, and we implemented innovative solutions that created real competitive advantages.

After my time with Laureate and Blackboard, Matt Small, a former Blackboard leader, invited me to join Simplicity. I worked there for five years, focusing on helping students see a return on their education investment—connecting with employers, building professional profiles, and understanding the importance of networking.

These experiences gave me a comprehensive understanding of higher education business processes and strengthened my network. Today, many former clients are now friends, and those relationships have endured through successes and challenges alike. That brings me to where I am now.

Great, excellent results. Now, tell us about Re-Skilling.AI—what problem is it solving with technology, specifically with Artificial Intelligence?

Considering the context of higher education and the rapid evolution of technology, I realized Artificial Intelligence isn’t just another tool—it’s a transformative force reshaping industries and everyday life. Companies in other sectors were quickly adopting AI to streamline processes, boost productivity, and reallocate freed-up resources. This got me thinking: how does this impact the job market?

After extensive research, including studies from the World Economic Forum, I noticed a mismatch. Companies struggled to find the talent they needed, while many university graduates had difficulty landing jobs. The gap often lies in the misalignment between university curricula and the skills employers demand. Unless these align, graduates will struggle to meet workforce needs.

That’s where Re-Skilling.AI comes in. The idea emerged almost by chance. During my son’s rugby practice, I chatted with another parent working on an AI project to match professional profiles with job requirements. We thought, why not build a solution to evaluate both soft skills, like emotional intelligence, and hard technical skills?

We started working on Re-Skilling.AI in July, creating a tool tailored to higher education. While universities focus heavily on assessing hard skills, soft skills—critical in today’s job market—often go overlooked. Studies increasingly emphasize the growing importance of these human competencies.

Re-Skilling.AI aims to fill this gap. Using AI, we developed a scalable, cost-effective evaluation tool to measure both hard and soft skills. The platform provides personalized feedback, enabling institutions to move toward one-on-one, customized education rather than traditional one-to-many models. It’s an ambitious vision, but one we’re determined to achieve.

Let me pause for a moment. Having seen the Re-Skilling.AI demo, there’s something remarkable I want to highlight. It’s the speed at which evaluations can be conducted. It’s like having an expert assess both hard and soft skills in a conversational, natural way—something AI makes possible at scale.

Without this technology, you’d need an expert to evaluate each individual, which would take an enormous amount of time, especially for an institution with even a modest student body of 1,000. The scalability just wouldn’t be there. What impressed me was the ability to deliver high-quality evaluations that are both precise and scalable. It’s like having a personalized expert for each student, providing accurate assessments that can also aggregate cohort-level data.

It’s similar to tools that diagnose an institution’s infrastructure at scale, generating a comprehensive report with a single click. What’s brilliant about Re-Skilling.AI is that it maintains the natural and human touch, which is essential. Traditional assessments—like lengthy questionnaires—are often too cumbersome, hard to update, and don’t effectively measure soft skills. Re-Skilling.AI fills this gap with an innovative approach that’s scalable, efficient, and insightful.

Thanks for the feedback—it’s spot on. Traditional methods for gathering this kind of data often rely on lengthy, tedious questionnaires that discourage participants and compromise data quality. Students need this data to build their professional profiles—the very reason they’re studying.

Scalability is crucial. Re-Skilling.AI enables rapid, consistent evaluations across multiple students, graduates, or groups, eliminating the diminishing returns and subjectivity of human evaluators. It also leverages prosody analysis, examining speech patterns like pauses and intonation to extract valuable insights for reports.

In just four or five months, we’ve secured our first client and are close to signing a second. We’re piloting Re-Skilling.AI with three or four clients across various fields, and the excitement is palpable. There’s a clear demand for this tool, with strong interest from universities in Ibero-America and the U.S. Re-Skilling.AI holds the potential to not only advance EdTech but also revolutionize professional development by bridging the gap between skills and career goals.

And it’s not like there’s a strict division—while there is a line between being a student in a learning process and then entering the workforce, that line is becoming increasingly blurred. Lifelong learning never ends; it’s a continuous process. It’s easy to see how this continuity operates under similar parameters, and it makes perfect sense.

I wanted to ask you about your transition—from being part of large, significant organizations with financial strength and specialized teams, to becoming an entrepreneur. What were your expectations? What happened as you anticipated, and what didn’t you expect?

It was a significant change. I’ve always had an entrepreneurial spirit but never felt ready to take the leap—until this year, when circumstances aligned, and I thought, “It’s now or never.” I decided to trust in what I’ve learned and give it a shot, knowing there are always ways to adapt if things don’t go as planned.

The biggest shift has been moving from financial backing to relying on my own savings. Yet, my approach to work hasn’t changed much. Whether in a large organization or now as an entrepreneur, my focus remains on creating value—identifying problems, improving processes, and delivering solutions.

Without a team, it’s more challenging. I’m leveraging AI tools to handle as much as I can, walking the talk to understand what’s achievable before expanding. This way, when I start building the team, I’ll know exactly what’s needed to maximize value.

I’m learning a lot and am pleased with the progress so far. There’s still plenty of work ahead, especially in commercial development, but that’s a strength of mine. Many startups struggle with effectively commercializing their products, but I’ve already secured some early wins, which makes me optimistic about the future.

I want to ask you about your experience as a sales leader and managing accounts, but first, what advice would you give to someone just starting in sales, relationship management, and commercial roles, especially in education? Or even beyond that—what skills and values should someone develop to reach your level of expertise?

I recently read an article where someone highlighted a key word for this field: honesty. I want to expand on that concept. This is, in general, a very small world. Although it may seem vast, especially in higher education, I’ve noticed over the past 10 years that the people we interact with—whether clients or providers—are largely the same.

It’s an ecosystem where, if you fail to deliver on a promise even once, that news travels quickly, creating barriers that can block the growth of your network. So, if I had to give one piece of advice, it would be to always strive for honesty in the relationships you’re building. Problems will inevitably arise—that’s true in almost every transaction. I can recall very few projects where there wasn’t some issue that required meetings and agreements to resolve. But those moments are crucial.

When you face challenges head-on, the other party sees that you’re reliable, and that builds trust. They continue to work with you, and that trust translates into ongoing business.

Networking is another essential factor. I mentioned it earlier, but I want to emphasize it again. Technical knowledge of the software you’re selling will change over time—throughout my career, I’ve sold all kinds of software for different purposes. What matters more is understanding the problem you’re solving and the value technology brings to that process.

For someone just starting in sales, consistency, humility, honesty, and a focus on building long-term relationships—through good times and bad—are critical to growth and success.

In your career so far, is there a particular project or client that stands out to you as especially meaningful? You’ve mentioned Laureate, but what else comes to mind? Why do you remember it so clearly?

There are certain projects that have marked my career. During my time at Oracle, for instance, I worked with Arcor, a multinational in the consumer goods sector that produces candy and food. I collaborated with them on various fronts.

In higher education, I have many memories, particularly of my work with Laureate institutions in Mexico, Chile, Peru, and Honduras. Another memorable project was with Duoc UC in Chile, a large professional institute. When I started working with them around 2014, they were in a challenging position—they had already purchased the software but were facing significant issues.

It was a hands-on situation where we had to “get our hands dirty,” as we say in Argentina. We had to roll up our sleeves, endure a lot of criticism, and fix things that weren’t working. Over time, we built a strong relationship and managed to increase the value of the contract by more than 50 times its initial worth.

It was a great success, especially since the software is still in use today with many of the parameters we defined during those challenging times. Back then, the system was running on-premise—cloud technology wasn’t yet widely adopted—so we had to address both academic and technical issues. I learned a lot during that process, and while this is just one example, it reflects my experience with other organizations as well. That project, in particular, opened my eyes to many new possibilities.

I imagine you wouldn’t expect something that initially seemed like a problem to turn into such a significant opportunity, right? It’s incredible. Now, I have to ask—since we’re both Latin American entrepreneurs looking out at the world—what’s your perspective on Latin America today?

That’s a broad question, so I’ll focus on education, technology, and adoption trends. Latin America is fascinating because of its diversity. While we share a common language, the cultural differences are vast.

From an educational perspective, the region often lags behind Anglo-Saxon countries, which typically lead in technology adoption and in establishing new processes—from student well-being to modernized curricula, learning formats, and student experiences. This trend still persists, but I’d like to see more innovation here.

That said, there are an increasing number of trendsetters in the region who continuously look at what’s happening elsewhere and try to implement those practices locally. Latin America has enormous potential and a wealth of talent that can teach other regions valuable lessons.

One of the region’s competitive advantages lies in its focus on soft or human skills, which are more pronounced here compared to Anglo-Saxon countries. If we can enable our societies to deliver on what we in EdTech have been working toward—personalized education, lifelong learning, micro-credentials, updated curricula, and student well-being—I believe we have tremendous potential to contribute to the rest of the world. That’s how I see Latin America today.

I’d never thought about Latin America’s natural competitive advantage in soft skills. Perhaps we haven’t given it the attention it deserves because we’ve been too focused on copying models from other regions. There’s so much potential there, and it’s a fascinating point—you’re right. Many things come naturally to us, but we haven’t applied the rigor needed to make them truly impactful.

For example, in Central American countries that are often in the news for being places where communities aspire to migrate north to improve their quality of life, I’ve found an incredible amount of talent. That’s just one example, but I’ve observed this across many regions I’ve visited.

What stands out to me is the resilience and adaptability of people in these areas when faced with complex situations. Latin America has endured volatile economic, political, and social cycles for decades. As an Argentine, I can attest to how we’ve had to overcome so many challenges. Surviving here requires developing skills that are highly valued globally: adaptability, teamwork, critical thinking, creativity, and resourcefulness.

Now imagine what could happen to this region and its communities if we combine these innate soft skills with other components already being developed in other parts of the world. The potential of this region is enormous.

I’d like to see more innovation in Latin America’s educational institutions. While many of them talk about the importance of innovation, too often it remains just words, not actions. That’s something I’d love to see change because, as a region, if we don’t adopt technologies at the necessary pace, we risk being left behind.

Juan Pablo, I also want to ask you: what do you value in a leader you work with? You’ve been in roles where you manage regions or markets, but what do you look for in a CEO or other leaders when collaborating with them?

What I value most is their human side. Of course, they need to have vision, execution skills, and the ability to be aggressive when the moment calls for it. There are times when you need to grit your teeth and push forward. But at the same time, they must never lose sight of the human aspect of the team they work with.

This is incredibly important to me, and I’ve been fortunate to work in organizations where I’ve experienced this firsthand. I want to highlight leaders like Martín Moreno and Matt Small, as well as others I’ve worked with in previous organizations. Their ability to value the team and understand their people stands out. Empathy is essential—it’s about understanding what others are going through, adjusting to their needs, and being there during both highs and lows.

When results are pouring in, it’s easy to celebrate together, but during tough times, when things aren’t going as planned, that’s when a leader needs to be present, listening, offering support, and coming up with new ideas rather than simply waiting for results because of their title.

For me, that’s the most important quality in a leader.

Now, to wrap up—almost—what are your plans for Re-Skilling.AI? What’s your vision for the next few years?

Right now, my focus is on helping higher education institutions adopt tools like Re-Skilling.AI to improve processes and outcomes. The goal is for students to gain the skills employers demand, develop strong professional profiles, and see a clear return on their educational investment.

I plan to start in Latin America and then expand globally, translating the software into other languages. Leaders in other regions agree this tool offers immense value, with no comparable solutions on the market.

But Re-Skilling.AI isn’t just for higher education. Companies can use it to evaluate employee skills and recommend tailored workshops or training programs, adding immediate value to their workforce.

The potential is enormous. The World Economic Forum predicts nearly 1 billion people will be impacted by global changes within 12–14 months—a rapid timeline. Many universities think this transformation is years away, which is a risky assumption.

Ultimately, I want Re-Skilling.AI to be accessible to everyone. Individuals could visit the website, complete an evaluation, and receive personalized recommendations to design their learning paths—whether through a university, professional courses, or alternative learning platforms.

The education sector often moves slowly due to regulatory constraints, but the rapid development of AI means the time to act is now. The market is huge, and we need to move quickly to make an impact.

Juan Pablo, before we finish, is there anything else you’d like to mention or add to the interview?

No, just a big thank you, Laureano. We’ve known each other for a long time, and this opportunity allows me to communicate and share through your platform and expertise.

I’d also love to collaborate with you on improving how we market certain aspects of the project. Thank you for your trust and for giving me this chance to speak.

‍

It’s been our pleasure, especially since we saw your launch and the demo, which convinced us of its massive potential. We’re thrilled to have conducted this interview.