Priceline, founded 26 years ago, might be “the OG of the online travel agency category,” but the brand’s marketing languished in recent years as new, savvy competitors including Expedia and Booking.com arose, said Lesley Klein, Priceline’s senior VP of strategy and brand marketing. That’s why, since taking on her role in April 2022, Klein has focused her efforts on modernizing the Norwalk, Connecticut-based brand and shepherding Priceline back into cultural relevance. 

“Especially in a category like travel that’s just booming, the opportunity to help reignite the heart and soul of the brand and make it meaningful to people and culture again has been really exciting,” Klein said.

Klein has transferred the experience she developed from leading WW’s 2018 brand overhaul to spearheading similar efforts in her year and a half at Priceline. She’s introduced a swath of new mediums into Priceline’s marketing—including social media, audio, streaming TV and influencer partnerships—and honed in on social commerce. 

Klein’s renewed focus on digital and social media marketing gave rise to Priceline’s Super Bowl campaign earlier this year, which saw the brand allocate its budget for the Big Game to a $5 million social media campaign with travel deals hidden in digital ads rather than invest in a pricey spot during the game. That campaign also served as Priceline’s first brand platform since 2019 and the first collaboration with the brand’s then newly appointed creative agency of record, Mirimar.

In July, Klein, 39, oversaw Priceline’s first-of-its-kind partnership with Amazon Prime Day, which offered consumers limited-time travel discounts on a custom Prime Day landing page throughout the two-day shopping event. 

“We are vastly outspent in the OTA [online travel agency] category,” Klein said. “And if we do the same thing as everyone else, instead of breaking through with these different opportunities, we are guaranteed to stay in that same position.”

If you could have dinner with one person, alive or dead, who would it be and why?

More than anything, a great dinner companion is a sharp and funny conversationalist. Ali Wong hits the nail on the head about women’s experiences. Her insights are cutting and delivery so precise. They say the best insights come from comedians because they offer a true and pointed look at life. 

What are the top two social media sites you use on a regular basis?

TikTok. To me, it’s most representative of what people are thinking and feeling and doing right now. And like many consumers today, TikTok is becoming my new search engine. [And] LinkedIn. I can’t overstate the value of my professional community and relationships as my career has progressed. 

What’s currently on your bedside reading list?

My bookshelf is an all-over-the-place mix of fiction and nonfiction. I’ve recently been between “The Tibetan Book of Living and Dying” and “How to Talk So Little Kids Will Listen.” I find I’m most able to access my creativity and a state of flow when I’m deep into a novel. I just finished “Tomorrow, Tomorrow and Tomorrow”—highly recommend. 

What was the last show you binge-watched?

"The Bear." I relate to the intensity and passion for a craft, the feeling of getting lost in what you do and the perpetual push and pull of balancing your passion with all the other things that make your life fulfilling.

At what age do you hope to retire?

For people who are innately energetic and ambitious, it’s truly hard to stop. I imagine I’ll always want to be creating and contributing in some capacity, but that may take different forms throughout different chapters of my career.