Grey’s Caroline Pay Explains Why She Left the Agency World to Join Meditation App Headspace as CCO

She starts Sept. 4 in L.A.

Caroline Pay is leaving the agency world. - Credit by Headspace
Headshot of Erik Oster

Grey London joint CCO Caroline Pay has left the agency to join meditation app Headspace in the newly-created role of CCO, effective Sept. 4.

Pay will lead Headspace’s creative team across content, design, marketing and communications, reporting directly to Headspace founder and CEO Rich Pierson.

“Having known and worked alongside Caroline since 2005, I have long regarded her as one of the most dynamic, innovative and original creative voices on the planet. As we enter an exciting era of growth and massive opportunity, there is no one I trust more with the Headspace brand than Caroline,” Pierson said in a statement.

Pay told Adweek she was vacationing in Los Angeles when Pierson approached her with the opportunity, telling her she was “the only person I trust with the brand” and to think it over on her return flight to London.

Although she was not looking to leave her position at Grey, she ultimately found that she couldn’t say no.

“By the time I landed at Heathrow, it was as if the decision had been made for me,” Pay said. “It’s a bit like when you fall in love, it’s like there is no choice, it just happens.”

Pay has been a fan of the Headspace brand since its inception, having attended co-founder Andy Puddicombe’s first Headspace guided meditation event in London and she now uses the app daily with her son. She has also long known Pierson, who like Pay spent several years at BBH London.

“Grey has been a phenomenal experience for me,” Pay said. “In 20 years in the industry, I’ve been incredibly lucky to work at some of the best agencies in the world.”

After leaving BBH London, where she served as deputy executive creative director and managing director, in 2016, she took time off to consider her next move. “I knew I wanted to do something different,” Pay said, “and actually I was looking to go client-side back then.”

“I hate being comfortable, I like being scared, and I like being challenged, and I like learning all the time,” she explained. “At the time … that felt a really good, scary thing to do.”

Instead, Grey London joint CCO Vicki Maguire told her “We’ve decided you’re the new CCO … and we’re doing it together,” Pay explained, “I thought that was literally the best idea in the world.”

Before joining BBH, Pay held roles at agencies including Mother, W+K and Karmarama. She has also played an important role in industry diversity initiatives such as The 3% Conference, SheSays and The Great British Diversity Experiment.

Pay called her time partnering with Maguire at Grey “the most phenomenal year,” adding, “For the first time I was working at a place where they completely understood what I was capable of … they allowed me to be myself in the best possible way.”

Looking forward, Pay is excited by the “huge opportunity to learn” afforded by working to grow a brand at the intersection of technology and wellness, as well as the move to Los Angeles. She hopes to “consolidate the amazing work they’ve achieved so far fulfilling the potential of the brand,” while “building a bigger, more famous, more recognizable brand.”

As their relationships with agencies change, Pay says it makes sense for brands such as Headspace to seek out a “more closer creative guardianship of the brand.”

“You need somebody central to the brand who has a vision for the brand … you need to have one person central that has a creative hold on it.”

@ErikDOster Erik Oster is an agencies reporter for Adweek.