Behind the Teams

The Power of Reps with Simon Hilton: Why the Speed of Shipping is the New Metric for Career Growth

Behind the Teams

Show Notes

In this episode of Behind the Teams, I sit down with Simon Hilton, the Head of AI Products at MYOB, to explore the intersection of leadership, team dynamics and the rapid evolution of technology. Simon shares his career mission of building great teams that build great products, emphasising that a high-performing team is the fundamental requirement for software success. The conversation dives deep into: The Leadership "Middle Ground": Simon describes his style as a balance between top-down direction and total autonomy, focusing on creating space for talent while maintaining strict accountability for results. The Kitchen Metaphor: A unique look at organisational strategy, comparing "McDonald’s style" teams that follow strict processes to "hatted restaurant" teams that innovate and solve complex problems. AI and the "Team of One": How AI is shifting roles from technical execution to managerial oversight, allowing individuals to manage "parallel agents" to ship products faster than ever before. The Future of Career Growth: Why "getting your reps in" through AI-enabled shipping can compress years of traditional experience into a much shorter timeframe.

More from Behind the Teams

Sep 21, 2026

On this episode of Behind the Teams, I sit down with Storm Jarvie, who has spent 18 years at the intersection of product, data, and experimentation, building and leading teams inside complex organisations before recently stepping out to work independently.

Aug 30, 2026

James Comer (Global Head of Strategic Workforce Management, ResMed) breaks down what strategic workforce planning actually looks like when 39% of the workforce needs new skills by 2030.

Aug 9, 2026

Jim Nelson has spent decades leading digital teams from scaling startups through a pandemic to selling luxury brands online but nothing quite prepared him for leading at Beyond Blue.

Jul 20, 2026

Simon Lester, Head of Product Design at Nuix, has spent his career proving that great teams don't need scale — they need proximity, trust and honesty. In this episode, Simon takes us back to the bosses who shaped him early on (the good and the genuinely bad), and unpacks what he's built since: small, high-functioning teams where mistakes are safe to make, feedback happens daily rather than in a monthly review, and nobody gets to hide behind the numbers.

See all episodes →