40 Under 40: How Mahmood Owolabi Turned His Problem Into a Viable Business

Fresh out of university, Mahmood Owolabi’s career took flight during the e-commerce boom in Nigeria, where he worked with a rising tech startup. As a co-founder of 

EdTech platforms, a disruptive Transition School, Owolabi has made a career out of doing the impossible. Precious Ugwuzor writes on his quest to train, mentor, and empower the next wave of tech talent ready to take on the world

Mahmood Owolabi is proof that persistence defines success. From navigating the hurdles of the UK’s rigid job market to co-founding one of the most disruptive EdTech platforms, Transition School, Owolabi has made a career out of doing the impossible.

Owolabi’s journey is a masterclass in defying odds and shattering glass ceilings. After overcoming a major barrier, he’s now rewriting the rules of career transitions for an entire generation of African professionals.

At a time when African talents are gaining unprecedented global attention, Owolabi is leading the charge, proving that the future of work is borderless. His mission? To train, mentor, and empower the next wave of tech talent ready to take on the world.

A Humble Beginning with Big Dreams

Fresh out of university, Owolabi’s career took flight during the e-commerce boom in Nigeria, where he worked with a rising tech startup. The experience was a formative one, sparking a lifelong curiosity about consumer behaviour and the “why” behind purchasing decisions.

“Witnessing the creation and engineering of platforms that attracted and retained customers sparked my deep fascination,” he tells Business Elites Africa.

It didn’t take long for Owolabi to translate that fascination into a career focused on marketing and consumer engagement, working with major brands like Airtel, Sterling Bank, Flutterwave, and Unilever.

His early career experiences laid a foundation for what would become a driving force in his professional life—understanding how to harness the power of marketing to build and scale tech businesses.

The Turning Point

Owolabi’s decision to relocate to the United Kingdom was a pivotal moment in his career. The UK, with its sophisticated tech market, seemed like the perfect place to further his ambitions. But it wasn’t the seamless transition he had imagined.

“I found it difficult to transfer my experience into the UK job market, which often emphasises ‘UK experience’,” he admits. This challenge is one that many international professionals face, and for Owolabi, it was a stark reminder of how certain job markets can be closed off to outsiders, regardless of their qualifications.

Instead of succumbing to frustration, Owolabi saw this as an opportunity for problem solving. He began documenting every step he took to secure job interviews, perform well in them, and eventually land offers. It worked. His first role at a tech startup in Wembley, North London, was the breakthrough he needed.

After updating his LinkedIn profile with this success, he was surprised by the flood of inquiries from friends and acquaintances—many of them fellow Nigerians—who were struggling with the same issue of transferring African work experience into the UK market. “It became clear that I wasn’t alone in facing this challenge,” Owolabi notes. His ability to navigate the UK job market became a valuable asset to others.

A New Opportunity

With his problem-solving instincts in full gear, Owolabi began offering career coaching to peers facing similar struggles. What he discovered was a critical gap in the market: while some African professionals could transition their skills to the UK job market, a significant portion – about 70% of those he mentored – could not.

“Their skills weren’t in high demand,” Owolabi recalls. This was particularly true for those not in tech-related fields, where job opportunities were abundant.

Recognising this need, Owolabi saw potential in the EdTech space. “This realisation highlighted the potential in the EdTech sector, and I saw an opportunity to be part of the renaissance of training people to fit into corporate roles,” he explains.

Teaming up with a software engineer, Yomi Omotosho, who was already working on similar challenges, the duo co-founded Transition School, an EdTech platform designed to help individuals transition into tech roles. The program offers six weeks of intense training, live project experience, and job readiness support.

Building Success

Owolabi attributes much of his success to a mindset grounded in continuous improvement. “Determination, continuous self-improvement, and surrounding myself with like-minded individuals have been critical,” he says.

His guiding philosophy—“Nobody is coming to save you” and “How bad do you want it”—keeps him focused on constant growth. Whether it’s upskilling himself or mentoring others, Owolabi’s commitment to self-improvement has been a core driver of Transition School’s growth, which has been achieved without external funding.

The school has trained over 100 students and counting, equipping them with the skills needed to thrive in tech roles globally. This success is built on Owolabi’s belief that true wealth isn’t just measured in financial terms but in the impact one has on others.

“I define wealth as impact,” he asserts. For him, wealth is about influence, education, and innovation—factors that create lasting legacies. It’s this definition of wealth that guides his work at Transition School, where he sees the potential to change lives through education and mentorship.

Empowering Africa’s Workforce

Owolabi is quick to point out that while the world’s perception of Africa is changing, there’s still a lot of untapped potential across the continent. “I used to call Africa a virgin territory, but that’s rapidly changing,” he says.

African entrepreneurs are leading this change, harnessing the continent’s most valuable resource—its people. Owolabi believes that as more entrepreneurs invest in education and skill-building, the continent will continue to rise as a global force.

“Thousands of jobs have been created, hundreds of thousands of lives have been touched, billions of revenue have been generated, and more investment is flowing into the continent like never before,” he observes.

His vision for Transition School is clear: to be the pipeline for the tech talent that will drive Africa’s continued growth. With increasing investments in various sectors, there’s a growing need to empower the workforce with the right skills.

“We aim to train individuals not just to meet the demands of their local economy but to become professionals capable of working globally,” Owolabi says.

Think Globally, Act with Purpose

For the next generation of African entrepreneurs and leaders, Owolabi’s advice is simple but powerful: think globally. “Do not limit your horizon to the continent,” he urges.

He sees enormous potential in stepping out of comfort zones and embracing the global stage, reminding future leaders that they are valuable players in a global ecosystem.

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His vision for Transition School is clear: to be the pipeline for the tech talent that will drive Africa’s continued growth…We aim to train individuals not just to meet the demands of their local economy but to become professionals capable of working globally