Innovating across time zones, the sky’s the limit for this comms leader

By Diane Schwartz, CEO of Ragan Communications.

She sometimes starts meetings at 5 a.m., and you might think that’s a bit early. But with her largest brand’s headquarters halfway around the world, Leslie Cafferty is one of the last to wake up among her executive set when she’s not traveling. She shows up for meetings before the sun rises in Connecticut with an agenda spanning crisis management to regulation to product launches.

As chief communications officer of Booking Holdings (parent company of KAYAK, OpenTable and Booking.com, with more than 20,000 employees), Leslie is shaping the communications strategy for the world’s largest travel agency.

Leslie and I caught up (at a “normal hour”) last month and I was intrigued by so many aspects of her role at Booking Holdings. But of particular interest is her relationship to her CEO, Glenn Fogel. It’s a much-coveted give and take between the comms leader and the head of the company. Leslie describes their work together as coaching and counseling. If they need to align, he always makes her feel like she can simply pick up the phone.

A 20-year tech company veteran with a passion for comms, marketing and promoting diversity in business, Leslie advocates for the critical role that communications plays in the C-suite. Having held leadership positions at major global tech companies Nielsen (as global VP of marketing and comms) and IAC (as director of global communications) prior to joining Booking.com in 2013, Leslie’s career has seen her work closely with many public company CEOs, managing corporate reputation and navigating complex communication challenges.

Leslie serves as the executive sponsor for Booking.com’s B.Equal Employee Resource Group, promoting equality and equity for women across the organization. Under her stewardship, B Equal has expanded opportunities for women’s visibility at local, regional and global company events, with a network of 3,000 women and male allies across the Americas, APAC and EMEA.

Leslie is on a quest to see as much of the globe as possible, with an impressive 69 countries visited so far. She spoke to me from her home in Connecticut, which she shares with her husband, three children and two kittens.

Leslie and her family

Origin Story

DIANE:How’d you get here? Share some significant stops along your journey to CCO of Booking Holdings.
LESLIE: My path to where I am today was not planned. I studied international relations in college and was contemplating law school. To help pay the bills my first year out of college, in addition to waiting tables, I took a job as an executive assistant at a large internet company called IAC.

I was enamored by the fast pace of tech and the world of business. IAC was a complex company full of brands constantly evolving through mergers, acquisitions and divestitures. How the company looked to tell that story to consumers, Wall Street and shareholders was fascinating and that piqued my interest in communications.

When an entry position opened up on the global comms team, I applied. Spoiler alert: I didn’t get it right away as I had no experience! But six months later they gave me an opportunity that began my 20-year journey.

DIANE: Did you know you wanted to be a communicator from early on in your career?
LESLIE: Not at all. My mother worked in academia and while my father had a successful career in journalism — I was never interested in following that path. I realized early on that I was quite interested in business and with my first company in particular (IAC), I relished the challenge to simplify complex stories about our investment strategies, the company’s value proposition and our long-term ambitions.

Great communicators need to be able to tell a story, but great communicators also need to understand the business inside and out and so path brought me on a journey where I have been able to match skills and interests I didn’t know I had early on.

Leadership

DIANE: What’s the most important quality a comms leader must possess?
LESLIE:Transparency. In today’s world, expectations for transparency from companies and leaders are at an all-time high. Your employees and customers may forgive you if you make a mistake, but if they don’t sense honesty in what you are saying and communicating — — both as a leader and with a communications hat on representing the company — you will lose them.

DIANE: A small percentage of CCOs report to the CEO like you do. How has this shaped your strategy and your influence in the organization?
LESLIE: It’s great to see the evolution of the communications function and to see how many more CEOs continue to value the function. While there is certainly collaboration with functions like marketing, the reality is that communications is a function that serves all aspects of the business.

We complement marketing efforts at times, but we support our finance & strategy teams on the investor relations front, our legal teams as we navigate new regulatory environments, and our people team as we navigate communicating with our 20,000+ employees. Reporting to the CEO allows visibility across all aspects of the business so we can effectively support all functions and stakeholders.

DIANE: How does this reporting relationship help a CEO?

LESLIE: It’s important for helping the CEO navigate his/her own communication. While there are consistent principles of communication I apply, how different leaders deliver a message authentically varies wildly, and having a strong relationship there allows for more tailored counsel.

DIANE: With nearly 100 communicators on the Booking Holdings team across the world, how do you engage and inspire them?
LESLIE: We work to create a continuous cycle of learning between all of us. Our communications org supports five major brands across more than 100 countries worldwide. So what we are working on varies, but we create connection points — whether big ones at our annual Communications Offsite, or smaller ones like quarterly check-in calls or steerco’s on particular topics.

We just launched a gen AI comms steerco to make sure we share best practices, and talk about what worked and what didn’t to inspire each other and keep knowledge-sharing going outside of everyone’s day-to-day.

Booking Holdings Communications Team.

DIANE: For women in leadership roles, there’s been slow but steady progress, with small percentages of women in CEO roles and board roles. What are some tangible ways to speed up change?
LESLIE: All leaders need to embrace a commitment of diversity and inclusivity within their organizations. Progress is not made when it is the responsibility of a task force or a single department. If leaders don’t recognize that diverse points of view lead to smarter business, organizations will not evolve.

Companies need to establish clear pathways to leadership positions, foster an inclusive culture through training and learning and development programs, provide equal access to high impact projects and measure and report progress back to the business regularly to ensure accountability.

Culture

DIANE: Tell us something about your brand that the ordinary consumer might not know.
LESLIE: Booking.com actually has very large homes/apartments/vacation rentals offerings, in case you thought Airbnb was your only option.

DIANE: What are some ways you’ve been able to bridge culture gaps across your global offices? Generational gaps?
LESLIE: We are a very large global business with operations all over the world, with more than 140 nationalities represented across our offices. This means that we have many cultural influences across our employee base — something we celebrate as we believe that diverse points of view are critical not only to our success but also to make sure that we can truly understand our customers’ needs wherever they are in the world.

While we embrace our diverse culture, we are united in our collective mission to make it easier for everyone to experience the world. This is our North Star and unites our 20,000+ employees globally.

The Work

DIANE: How is generative AI helping you and your team to be better communicators? And tell us a little about the Innovation & Enablement Team there.
LESLIE: Gen AI will have far-reaching impacts across all of society — spanning industries and functions within business. It’s early days but we want to be ahead of the adoption curve, not behind it. While we are all interested in testing the new technologies available — and there are SO many — if it’s everyone’s job, then it’s no one’s job, which is why we are creating an enablement team within our communications department, which will have annual goals related to testing, implementing and scaling the right technologies across our organization.

Gen AI tools can help with overall ideation, content creation, image and design creation, editing, and more. How well the tools can be prompted to tailor to your company’s or leader’s tone is the difference between good and great output. We are also in the process of building our own databases with tailored information that can help us easily scale communications plans on various topics. A lot more to do in 2025!

DIANE: What are a few major trends and developments facing the travel industry?
LESLIE: Personalization is the biggest trend we are seeing in travel right now, and this trend spans far beyond just the flight or hotel.

The options for consumers are endless, and travel is so much more than just the destination. It’s what you do there and how you experience things that makes or breaks a great trip. Digital travel assistants who know who you are, your preferences (red wine or white? Steak or vegetarian? Vacation home or hotel? Skydiving or hiking?) will be able to create experiences that today may take days or months to research and plan. These tools will be powered by gen AI and we are already testing and rolling these out across our major brands.

DIANE: What are some key trends you’re seeing for communications for 2025?

LESLIE: Further diversification of channels and content formats globally both externally (TikTok, live chat, vlogs, voicechat, livestreaming, etc.) and internally (Slack, email, workplace, WhatsApp, etc.) Communicators need to know where their audience is and how to communicate with them on their channel of choice. A one-size-fits-all message does not work in today’s world. It’s becoming much more complex and dynamic to get it right.

Self

DIANE: What are some ways you unwind on a typical workday?
LESLIE: The best part of my day is if I can get in some exercise. I find it is truly a time to step outside of myself, my inbox and all of the immediate to-do’s and think at a higher level. What is most important for today? What will I prioritize? What am I not thinking about that I should be? At the end of the day,

I enjoy cooking, which helps me transition from a high-intensity mood to a more relaxed mood.

DIANE: What are you still working on improving?

LESLIE: I am always working on prioritization… Am I spending my time (in work and in life) in the right places that are having the highest impact on me personally, my company, my team, my family, etc. It’s really hard to know but I ask for feedback from those around me often.

DIANE: Travel is a big part of your life – what’s your favorite destination and what’s on your travel wish list?
LESLIE: It’s hard to pin one place! I want to see as much of the world as I can in my lifetime, and new places and experiences give me energy. My first trip to Japan stands out as a memory for me of an incredible place that reminded me how much of the world I still need to experience.

Other Tidbits

Favorite book:
Jane Eyre

Best Advice:
Life is full of chance and luck, far more than one’s own ability to control it.

Worst Advice:
Take up rowing (I invested in the machine but never use it!)

Best Mistake:
All of them. Mistakes are how you learn.

To all Wonder Women: If you’re looking to connect with other women leaders in communications, consider joining us for the next Ragan’s Business Summit & Retreat in September 2025: Details are here.