Description

From graduate engineer to CTO, Andrew Phillips’ 16-year journey at Skyscanner is a story of continuous reinvention. He didn’t chase titles—he chased growth, deliberately stepping out of his comfort zone and unlearning the habits that no longer served him. What’s kept him at the company for over a decade isn’t status, but challenge: new teams, unfamiliar problems, and the chance to stay close to the work, even as his scope of leadership expanded.

In this episode, we explore how Andrew is now applying that same mindset to leading in the AI era—personally and professionally. He shares how he’s built a personal AI stack to stay more present, how Skyscanner is blurring traditional team roles to unlock speed, and why “directed autonomy” is more important than ever. For leaders navigating scale, technology, and the desire to make meaningful impact without burning out, Andrew offers a powerful perspective.

Key Takeaways

• Growth through discomfort: Andrew’s biggest accelerations came from switching roles and leaving his comfort zone—not climbing a predefined ladder.
• AI as a leadership enabler: He uses AI tools to be more present, thoughtful, and effective—especially during high-stakes meetings.
• From feature factory to outcome focus: Leaders must reconnect people to impact, not just output.
• Directed autonomy: Empowering teams with AI means giving clear goals—not micromanaging the execution.
• Unlearning process overreach: Traditional roles, ticketing systems, and rigid handoffs are ripe for reinvention in AI-native organizations.

Additional Insights

• The personal AI stack Andrew uses includes ChatGPT, Otter, Cursor, and SpecKit—enabling him to ideate on walks, build apps during board meetings, and maintain strategic presence.
• Skyscanner’s senior engineers are back coding, using AI to close the gap between architectural thinking and execution.
• AI-driven productivity unlocks don’t just mean faster work—they mean better work-life balance, deeper engagement, and more human leadership.

Episode Highlights

00:00 – Episode Recap

Andrew Phillips shares how stepping into uncertainty—and building his own AI stack—transformed his leadership at Skyscanner. From personal growth to organizational reinvention, he’s leading the charge on what modern technology leadership looks like.

01:35 – Guest Introduction: Andrew Phillips

Barry introduces Andrew Phillips, CTO of Skyscanner, reflecting on their 15-year relationship and Andrew’s rise from graduate engineer to technology leader.

05:45 – The One Trick Pony Moment

Andrew recalls the pivotal moment when a CEO challenged him to move teams and stop playing it safe—triggering his real leadership evolution.

12:33 – Starting with Yourself in AI

Before transforming your company with AI, Andrew urges leaders to start by experimenting personally and learning from the ground up.

15:15 – Writing Better Prompts, Building Better Specs

AI tools thrive on clear direction. Andrew realized that better prompting and crisp product requirements accelerated his results dramatically.

20:01 – Directed Autonomy in the AI Era

Giving AI tools (and people) the “why” rather than micromanaging the “how” builds trust, speed, and better outcomes.

24:56 – Parallel Productivity and Boardroom Apps

How Andrew built an entire app—during a board meeting—by offloading work to AI and staying fully present in the room.

27:13 – Reclaiming Work-Life Balance

AI allows Andrew to unload his mental backlog—using...