Women in Business Q&A: Leslie Cafferty, The Priceline Group

01/27/2017 10:23 am ET

Leslie Cafferty is the Vice President and Head of Global Communications for The Priceline Group, the world’s 3rd largest global ecommerce company operating six major brands: Booking.com, priceline.com, KAYAK, agoda.com, rentalcars.com and OpenTable.  In this role she is responsible for overseeing all corporate, financial, brand, crisis, executive and internal communications initiatives for the Group, which has dual headquarters in Norwalk, CT and Amsterdam, and operations in more than 200 countries.  At the Group, Cafferty drove the Communications strategy for the company’s largest acquisitions (KAYAK and OpenTable), developed the international consumer brand PR strategy for the Group’s leading business, Booking.com, and overhauled the internal communications strategy for a company of 16,000+ employees. 

Prior to her role at The Priceline Group, Cafferty served as a Vice President of Communications & Marketing at Nielsen, the world’s leading global research company. In this function Cafferty developed the company’s global PR strategy for Nielsen’s fastest-growing division (Digital) and drove the Marketing and PR strategy for Nielsen Twitter TV Ratings, the company’s ground-breaking move into social TV analytics in partnership with Twitter.

Before Nielsen, Cafferty spent eight years at IAC, a leading Internet company operating more than 25 market-leading digital brands including Match.com, Tinder, Vimeo, The Daily Beast, and About.com.  During this time she served as the Director of Corporate Communications, overseeing the Communications strategy for all major corporate transactions including multiple acquisitions, spin-offs, mergers, joint ventures and corporate investments, in addition to driving brand PR initiatives at a number of IAC’s brands, including Electus and Match.com.

Leslie graduated Magna Cum Laude from Lehigh University with a degree in International Relations.

How has your life experience made you the leader you are today?

I grew up in a family that very much valued hard work, integrity and never taking short cuts. That not only instilled a strong work ethic in me, but it taught me two things that have shaped me as a leader today: 1) You have to get your hands dirty if you want things done the right way, and 2) You have to empower others to get their hands dirty if you want to create strong leaders in your organization. I try to lead by example with my teams. I don’t just delegate work. I do work, at every level. When the team is in a pinch or being pushed, I am right there with everyone helping to do whatever we need to do to keep our organization moving the business forward. Diving into work across all levels of the team helps us get done what we need to get done, helps keep my team feeling connected and motivated, and helps me continue to stay relevant in my field. But I have also learned that I can’t always do it all myself, and the best way to let strong talent flourish is to empower them to make decisions and take ownership of the accompanying work streams.

How has your previous employment experience aided your tenure at Booking.com?

I have spent the majority of my career working for Internet companies, and there are a certain set of skills required to thrive and succeed in this environment. Technology companies move quickly. It’s a test-and-learn culture where success happens quickly and failure happens quickly. Expectations are high and resources are lean. People who succeed in in the Internet are people who can creatively identify opportunities, make decisions quickly and use data to inform strategy, investing and prioritization, and this applies to Communications just as much as any other function. I have learned this through many of my own test-and-learn experiences. I have made mistakes along the way, but I have learned how to operate under pressure, make big decisions quickly and inform and defend actions with data. I still make mistakes but I have learned how to navigate the fast-paced world of tech, which has helped me immensely in my role within a company like Booking.com which is one of the largest tech companies globally and growing global scale at an incredibly fast pace.

What have the highlights and challenges been during your tenure at Booking.com?

Working for a global company of this scale will always come with challenges, but those same challenges have also become some of my favorite moments during my tenure at Booking.com. Booking.com is a European business at heart, and expanding into major new markets like China and the U.S. have been major moments of challenge and excitement in recent years. Navigating different media landscapes and different cultures defined by different values with one global consumer product creates a unique set of challenges in every market, but testing our way to moments of success has made my team think in new ways. This has proven thrilling for those unafraid to make small mistakes on the bigger path to success.

My team at Booking.com has also been more internationally diverse than my teams at prior companies. This is absolutely one of the biggest highlights because the perspectives and opinions coming from cultures all over the world has led to some of the most interesting debates and creative experimentation of my career. But this too, is not without its challenges. Navigating cultural differences in work culture – from expectations to time zones and even vacation schedules creates complexities that aren’t as common when operating a team within a single market.

What advice can you offer to women who want a career in your industry?

It’s no secret that we need more women in tech, and I am an advocate for that. My advice to women is not to be intimidated by tech. I think some women are intimidated because it is a male-dominated, or engineer-dominated world, but that is changing. Women are users of tech, yet the products continue to be conceived of, made of and marketed by men, which is a huge opportunity for women. I certainly encourage more women to explore careers in engineering and information technology, but you don’t need an engineering degree to be a successful leader in this space. Yes we need more female engineers, but we need great writers, great marketers, and great business acumen. The biggest and best companies recognize this and there is incredible demand out there for women who put themselves forward.

What is the most important lesson you’ve learned in your career to date?

The absolute more important – but hardest – lesson I’ve learned in my career is to trust my confidence. I have always been a relatively confident person when it comes to my brain power, but I have many times been a victim of intimidation or paralyzed by the fear of failure. I have learned that the only way to excel and move up in my career is to trust my confidence. It means making big calls and taking big risks, but over time, as my risks – based on confident analytical and decision-making skills – have resulted in wins for the company, this has allowed me to slowly begin to trust my instincts more. I too, have failed and made many mistakes, but I have come to find that my superiors often don’t mind mistakes if I can take away critical learnings for the organization.

How do you maintain a work/life balance?

I wish I had a nice, neat answer to that question. The reality is that I don’t believe there is ever balance. When I am working, I think about the time I could be spending with my kids. When I take time for myself, like, say, for a run, I think about the work I could have gotten done within that hour. When my husband and I choose to go out on a Saturday night, we wonder if we should spend more time with the kids. But if we spend a Saturday night with the kids, we wonder if we’re making enough time for our marriage. I question my “balance” all the time, and I have come to learn that second-guessing my choices is, at times, a part of life. But I think that’s part of what makes me human. I have a passion for many different things in life, and an energy to try and do them all well.

I don’t think there is a secret formula for balance. I just think everyone needs to find their own homeostatis. I believe that if people do what they need to do to feel fulfilled as a human, that’s when they truly thrive at work, as a partner, as a mother or at whatever it is they love to do.

What do you think is the biggest issue for women in the workplace?

I think confidence and trusting in confidence can be debilitating for women in the workplace, as I talked about above, but I think this is a personal/people issue, not workplace issue. The business world is far from perfect when it comes to total equality, and every company is responsible for its role in working toward this ultimate end goal, but the reality is that the workplace has come a long way. I am of course lucky to work for a company that places value on women and gender diversity, but the biggest issue is making sure we, as women, take advantage of all that we have in front of us. I encourage women not to let the stigma of inequality impact their focus on doing what they need to do and making the decisions they need to make to positively influence their organization. The more women can lead by example, the more we will create the proof and data needed to make sure the business world continues to understand the value women bring to an organization, thus incentivizing the companies themselves to take on the ownership of gender diversity and equality in the workplace.

How has mentorship made a difference in your professional and personal life?

Mentorship has been incredibly important in my professional life. I have had some amazing male and female mentors along the way that have pushed me far beyond what I thought I was capable of, which ultimately helped catapult my career in many different ways. Mentors can’t be chosen, and are almost impossible to identify. My most influential mentors were people that I never would have anticipated upon initial meeting. They are often people who have challenged me from the outset, but I thrive under the pressure of a challenge. Its many of the people who push me the hardest that have ended up teaching me the most.

The mentors in my personal life are of a very different nature, although not less significant. My life mentors are those who support rather than teach or challenge, but I have come to learn a lot about myself as a mother, a friend, a wife, an executive and as a daughter through the unwavering support of the people I would call my life mentors.

Which other female leaders do you admire and why?

There are so many women I admire, and most are many of the women I have worked with day to day in my own career over the years. I admire commitment and integrity above almost any other character attributes, and it’s more difficult to evaluate the commitment and integrity of people I have not worked directly with. But in terms of very public female leaders, I have always admired Indra Nooyi because during her decade + at Pepsi she has embodied long-term commitment and dedication, growing and shifting the direction of the business, and I believe it must require a level of integrity to have such a long-term positive impact on an organization’s business and culture.

What do you want Booking.com to accomplish in the next year?

Booking.com is truly one of the most remarkable businesses I have ever observed. The business has slowly and quietly become one of the world’s largest e-commerce companies with an incredibly loyal customer base growing all over the world. It’s an extraordinary story of entrepreneurship, a test-and-learn technology culture, incredible diversity and smart, but fearless, business leaders. I want to see the company continue to succeed under the same values and principles that pioneered the creation and success of the business to date, and as a Communications leader, I want to tell the company’s stories in a way that supports our principles, our people and our culture.

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