Always On
If it seems like the world’s in permanent crisis mode — that’s because it is. But what does all this mean for the world’s biggest companies?
On Always On — a podcast about branding, communications and corporate reputation — host Shahar Silbershatz searches for the answers.
He meets brand, marketing and communications experts — including Chief Communications Officers (CCOs) and Chief Marketing Officers (CMOs) — to learn how they’re steering leading companies through our age of uncertainty.
Always On
Booking Holdings' Leslie Cafferty on Why Comms is a Two-Way Street
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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