Building the Workforce of Tomorrow: Insights from our CHRO Roundtable with Helen Kontozopoulos

In our latest CHRO & People Leaders Roundtable at Endeavor Greece, we had the privilege of hosting Helen Kontozopoulos - Founder & CEO of Resiin, Adjunct Professor at the University of Toronto, and a seasoned entrepreneur and operator with extensive experience scaling companies and building talent. Together with a select group of HR and People leaders from scale-ups, tech companies, and influential players in the Greek and global talent ecosystem, we dove deep into one of the most pressing topics for any growing organization today: how to effectively upskill, reskill, and future-proof your workforce.

The Emotional Side of Scaling

Helen opened the discussion with a refreshingly honest note: "The fear is real." Behind the headlines of rapid growth, every scaleup journey is filled with uncertainty, people dynamics, and constant evolution. Whether it's navigating founder transitions, balancing academic and business careers, or expanding teams across geographies, Helen’s own story highlighted how leadership is as much about managing emotions as it is about strategy.

AI Upskilling: Hype vs. Reality

A key theme throughout the discussion was the tension between AI as an enabler and AI as a shortcut. Drawing from her experience both in academia and as co-founder of ODAIA (an AI-powered SaaS scaleup), Helen emphasized that while AI tools can automate certain tasks, domain expertise remains irreplaceable - especially in highly regulated industries like healthcare and pharma.

In one real-life example, Helen described how her team tried to use AI-generated LinkedIn posts created by staff unfamiliar with the industry. Despite the technology, the absence of deep industry understanding led to significant missteps. The lesson? AI can assist, but it can't replace context, critical thinking, and expertise.

Upskilling is About Asking Better Questions

Rather than simply training employees to use AI tools, Helen advocated for upskilling team members on how to ask the right questions. In her view, the true superpower of tomorrow’s workforce will be “interdisciplinary questioning” - developing the business acumen, problem-framing skills, and cross-functional understanding needed to collaborate with both humans and machines.

The "Glue" of an Organization

Beyond technical skills, Helen emphasized the importance of recognizing - and protecting - the "glue people" inside a company: the individuals who may not carry formal management titles but hold essential informal knowledge, foster cross-team communication, and keep information flowing. As AI adoption accelerates, organizations risk overlooking this critical interpersonal layer that often makes or breaks collaboration.

Growth Without Management Pressure

Participants around the table also shared their own challenges: how to balance growth while not forcing top-performing individual contributors into management roles they don’t want. Several companies described efforts to design alternative growth paths, allowing key talent to stay technical or specialized while still being recognized and rewarded for their impact.

The Role of HR in the Age of AI

For HR leaders, the conversation was clear: their role is expanding from traditional hiring and compliance into becoming organizational architects - helping companies structure knowledge, capture informal learning, support internal mobility, and ultimately ensure that both people and data are flowing in ways that allow companies to scale sustainably.

💡 Key Takeaways

• AI is a tool, not a substitute for expertise. Domain knowledge and critical thinking remain crucial.

• Upskilling starts with better questions. Interdisciplinary thinking will be a key skill for the future.

• Protect your ‘glue people’. Informal knowledge holders are often the most irreplaceable.

• Create non-managerial growth paths. Not every top performer needs to become a manager.

• HR’s role is evolving. It’s increasingly about organizational design, knowledge management, and enabling cross-functional fluency.

The conversation was a timely reminder: while AI, automation, and fast growth are reshaping companies, at the heart of every scaleup remains what matters most - its people.