Cal Thompson, VP of Design on how they use AI at Headspace and why they hire interns

With so many AI tools flying around, it’s easy for creative teams to feel overwhelmed. Which tools actually matter? And more importantly, what stays uniquely human in design leadership as technology evolves?

In this episode of Design Leadership in the Boardroom,Ekaterina sits down with Cal Thompson, VP Design at Headspace and curator of Future London Academy’s Product Design Strategy course. Cal shares how AI is changing the strategic power of design (not replacing it), where these tools genuinely help guiding roadmaps, measuring product signals, prototyping visions, and where they don’t belong at all, especially when it comes to anchoring human stories.

Joining as a special guest, Rachel Arredondo , Senior Product Designer at Headspace, offers a practical, grounded view of AI as a thought collaborator. She shows how she uses Claude to expand her reach without outsourcing judgment, and why designers must shape tools just as much as tools shape us.

Expect a conversation rooted in empathy, culture, and creative responsibility, plus a clear, usable framework for deciding where AI fits in your design process.

What you’ll learn 

• Why design’s strategic influence can grow in an AI-enabled world
• Where AI helps most across the process of guiding roadmap, synthesising measurement signals, prototyping future visions, navigating crowded markets
• Why human observation and interviews can’t be replaced by synthesis tools
• How to build a design culture that fuels collaboration, trust, and imagination
• What AI means for junior talent, and how leaders should rethink career pathways
• Why the next “design movement” will be collective, not solo-AI driven

Who this episode is for

Design Leaders · Product Designers · Head of Design · Head of UX / UX Director · Product Design Lead · UX Design Lead / Design Lead · Design Managers & Senior ICs navigating AI adoption · Solo/In-house designers · Creatives and cross-functional partners (PMs, researchers, engineers) shaping AI-enabled products