The AI Skills Gap Is Real: Here’s how one Leader closed it fast
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Three years into his role leading engineering teams at Risepoint, John Maltese found himself in an uncomfortable position. Despite being Director of Engineering of the ed-tech company that employs over 100 engineers, he was falling behind on the technology that could help transform his company.
“I had almost three years of experience leading engineering teams already,” John explains, “but things were getting static and I was falling behind on AI.”
He is not alone. Across all industries, leaders are grappling with the same challenge in the face of rapidly emerging AI tools.
It’s precisely this issue that drove Alina Vasile (Director of Growth & Product) to develop and launch Codesmith’s innovative AI & ML Technical Leadership program (AITL). Drawing on a decade of experience at the intersection of emerging technology, education, and user empowerment, Alina recognized that mid-level engineers needed more than just AI training, they needed to learn how to lead with AI.
John explains how graduating from AITL reinvigorated his career. His transformation illustrates exactly what Alina envisioned when she created the program.
“I've taken lots of different types of courses in my life and I've never done one that had such immediate beneficial results”
Risepoint employs around 100 engineers, yet none possessed the AI and machine learning expertise needed to scope out opportunities these rapidly evolving tools could provide. New models and releases emerge daily, leaving even experienced technical leaders struggling to keep pace.
“There's very few people at Risepoint, and probably very few people at most companies, that feel completely on top of what's happening in AI,” John explains.
This knowledge gap extended beyond the engineering teams. Risepoint's C-level executives "felt underprepared" to make critical decisions about enterprise licenses, tool selection, and company-wide AI adoption strategies. The decisions were too important—and costly—to make without the proper knowledge.
The decisions around integrating AI into the company are ones being faced by most industries today, even outside tech, as we step into a world where all businesses become “if not AI companies, at least AI-enabled”.
These decisions are how to drive adoption of the tools among the staff, how to train them in using the tools, which use cases are valuable and applicable, and where AI and ML could be applied to deliver the most impact.
John spotted an opportunity when he found out through the Codesmith community about the launch of AITL.
“There are big decisions to make around AI, so it was a no-brainer for me to do the program,” John says.
John enrolled in the AITL program's inaugural cohort in January 2025. Alina had designed the program specifically to address the gap in the market—experienced engineers who needed to become AI leaders, not just AI practitioners.
“The turnaround on the program, the tools it gave me, and the expertise it gave me were invaluable in my career development and to my company”
"The program really made me very comfortable working on and developing RAG systems from scratch," John explains. "90% of what I do—and probably 90% of what other AI engineers or AI specialists are doing—are RAG-based models [Retrieval-Augmented Generation, a technique that enhances AI responses with relevant information]. That's the foundation of the work that I do and I learned all that through the AITL program."
“The goal wasn’t just to upskill engineers in AI techniques, it was to equip them with the systems thinking, strategic frameworks, and technical depth needed to architect and lead AI adoption across their organizations.”
— Alina Vasile, Director of Growth & Product at Codesmith
The results were dramatic and immediate. Upon graduation, John's role at Risepoint fundamentally shifted.
“I've taken lots of different types of courses in my life and I've never done one that had such immediate beneficial results,” he says. “Once I graduated I was immediately considered a credible source of AI knowledge at our company.”
This credibility translated into expanded responsibilities that reached far beyond his engineering teams. John now presents his AITL learnings to Risepoint's boardroom, advising directors, the CTO, head of security, head of product, head of engineering, and managers on the company's AI future.
“That's something I would not have been able to do before the program.”
His influence extends into areas traditionally outside an engineer's scope. John now advises the entire vendor management team on contracts, technology investments, rollout strategies, and productivity optimization through AI tools.
The transformation proved so valuable that Risepoint decided to sponsor John's program tuition retroactively. They also selected him to represent the company at the AI summit in San Diego in February—a clear signal of how much they value his new expertise.
“Once I graduated I was immediately considered a credible source of AI knowledge at our company”
John's story exemplifies what Alina envisioned when creating the AITL program: technical professionals who could bridge the gap between AI capabilities and business strategy.
Much of Risepoint's current AI strategy now stems directly from knowledge John gained through the program.
He runs training sessions for fellow software engineers at Risepoint, while simultaneously educating senior leadership about AI possibilities and limitations. This dual role of technical expert and strategic advisor represents the kind of career evolution the program was designed to enable.
"The turnaround on the program, the tools it gave me, and the expertise it gave me, were really invaluable in my own career development and to my company," John reflects.
John's journey from stagnating engineering director to strategic AI leader demonstrates the impact of the Codesmith approach to AI. Rather than simply teaching technical skills, the AITL program develops the leadership capabilities necessary to guide organizations through the most significant technological shifts in history.
Ready to energize your own career and learn to lead with AI? Discover how Codesmith's AI & ML Technical Leadership Program can transform your professional trajectory.
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