Navigating Technology Leadership in an Era of Unprecedented Change

Rupert's keynote explored how artificial intelligence (AI), shifting market dynamics, and new models of leadership are reshaping executive careers and board-level opportunities.

Technology Leadership in Transition

“We are probably in the greatest period of change in technology in living history,” Rupert noted. AI has moved beyond being a specialist function and is now a core competency for leaders across all disciplines. Organizations are experimenting with roles such as Chief AI Officer, but the long-term trend is clear: leaders in every function—from legal to product management—must understand and apply AI to remain effective.

Market Trends and Workforce Shifts

Following the post-COVID tech boom and contraction, the market is now rebuilding. While large-scale layoffs have reshaped sales, marketing, and go-to-market functions, leadership roles remain pivotal. Companies have not yet cracked true skills-based hiring, but Rupert sees a future of agile “tiger teams”, where adaptability and broad competencies matter more than narrow functional expertise.

What Makes an Executive Attractive Today?

Executives looking to stand out must show impact and relevance rather than relying solely on job titles. Transferable skills, sector shifts, and proactive positioning are becoming key differentiators. Rupert emphasized that:

• Networking outweighs headhunters. Only around c.5% of executive roles are filled by search firms; the rest come through proactive engagement and visibility in the industry.
• Clarity is critical. CVs and LinkedIn profiles must highlight achievements, contextualize company experience, and articulate transferable skills.
• AI literacy is non-negotiable. Regardless of role, leaders must understand how AI affects their domain.

Essential Skills for the Next Generation of Leaders

Executives aiming for director or C-level roles should cultivate:

• Leadership – inspiring followership and engagement.
• Intellectual dexterity – solving problems across functions.
• Intellectual honesty – recognizing gaps and learning.
• Deep expertise – recognized authority in a discipline or sector.

These qualities, combined with adaptability, position leaders for success in a market where roles and structures continue to evolve.

Action Points for Executives

• Articulate your value clearly. Focus on measurable achievements and transferable skills.
• Engage with networks. Stay visible through industry events, thought leadership, and proactive outreach.
• Build AI fluency. Understand AI’s impact on your function and demonstrate readiness to apply it in leadership contexts.

Final Word

As Rupert reminded the audience: “The lion’s share of potential opportunities will come from being heavily engaged in the industry you want to be successful in.”

For today’s executives, success lies not in waiting for change - but in leading through it.