In the Season 2 finale, Leslie Cafferty, Chief Communications Officer at Booking Holdings, shares how her team leads communications across brands like Booking.com, OpenTable, and KAYAK in a world that’s always on — and always shifting.

From experimenting with AI tools to navigating public backlash during the pandemic, Leslie explains why today’s communications landscape requires constant iteration, cross-functional collaboration, and — above all — listening. She reflects on building internal trust, staying ahead of risk, and offering clear-eyed counsel to the CEO when the pressure is on.

For Leslie, communication isn’t just about sending messages — it’s a two-way street that demands curiosity, clarity, and the courage to adjust course.

Time stamps

00:00 Communication as a Two-Way Street

00:21 Meet Leslie Cafferty

01:48 Leslie's Career Journey

03:52 The Evolution of Communications

05:20 AI and Technology in Communications

11:24 Experimentation and Data-Driven Strategies

20:34 Reflecting on Achievements and Challenges

21:05 Navigating the Fast-Paced Communication Landscape

23:41 Crisis Preparation and Response

26:39 Learning from Public Backlash

28:48 Fostering Open Internal Communication

33:02 Collaborating with the C-Suite

34:25 Deciding When to Speak Out

39:09 Personal Insights and Switching Off

40:27 Conclusion and Farewell

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