This week, we're sitting down with Anna Cupples, a senior engineering leader whose career has spanned Orion Health, Air New Zealand, and Trade Me. We discuss the pivotal moments that turned a software developer into a leader, how her early career shaped her approach to engineering, and what the rise of GenAI really means for young people entering the tech workforce today. We also get into the honest, unfiltered reality of being a woman in tech leadership, from navigating systemic hurdles to building mentorship cultures that actually work.