Caroline Pay

In Conversation

Caroline Pay has been a force within the advertising industry for 20 years. Starting her career at Mother, her path has been to shape the culture not only at Mother but at BBH and Grey, working with strong clients such as Boots, Levi's, Tesco and Coke. Swapping London for LA a few years ago, she has recently been immersed in the exponential growth of the global mindfulness app Headspace. Having attended their first meditation event in London, with her friend Rich Pierson she saw them grow from a live events company to the phenomenal global app they are today. She is now the CCO, bringing her vision and creative point of view to their mission of improving the health and happiness of the world. She is also on the board of OK Mentor, and is passionate about what she calls "unleashing the power of creativity in young women".


WF: I know you as a queen of creative agency culture – how has being at home been for you?

CP: Going into the office plays a very important role for me, as a working single mum. As I walk through the doors of the office, a physical transformation happens. I became CP (which is what they call me at work). It helps me mentally change into work Caroline, and I miss that. For me, work has always been a stage. I think back to climbing the concrete stairs at Mother. It was like going onto a stage. It's the same at Headspace. I walk into the open-plan room, and I sing a really high opera note every morning – and whoever's in the office harmonises with the note. It's just ridiculous, but it's an arrival thing. After that I am fully focused on work.

WF: Agency culture has traditionally been a very white male environment. Women have played a lot of supportive roles but fewer creative leadership roles. Did you ever feel your gender was a problem for you?

CP: Early on I think I was lucky. Later on with certain individuals, yes. When I started I was the only girl at Mother. When Kim [Gehrig] and I teamed up we were seen as the ‘the girl team’ (whereas we knew we were just the best team), so we resented that a little bit. As we got older, taking on more responsibility, we realised we were role models. So we did have to take responsibility for equality in advertising and speak up about it and encourage young girls, and call out old men when they were inappropriate.

WF: Did you feel a change when you became an actual mother?
CP: When I got pregnant with Buddy, I thought, ‘Cool, now I can be a stay at home mum and bake apple pies and just relax and garden.’ I had all these weird domestic goddess ideals. And then as soon as I was at home with a baby, I was like, fuck this, this is horrendous! This is not me, I'm terrible at home, I'm terrible without an audience, this baby doesn't appreciate me. You know? So I had a realisation that my job had a huge role for me as a person. I believe I can solve any problem with my thinking, and I wanted to do that, it gave me power and made me happy.

WF: And how did the framework adapt for you?

CP: I was very, very clear that I was setting boundaries. Boundaries are the key to being a working parent, in my opinion. And having a team around you that respect the boundaries – right? You can't set boundaries with idiots because they don't care. But I was really lucky that I was in a senior enough role to set them. And my team were just very respectful, because they knew that when they had me, they had me one million per cent. Then at 6 pm I'd say, ‘See you later’, and then they get me the next day.

WF: It's exciting to think that young women coming into the business might imagine that they can also have an incredible career, be at the top of their game, have a family and that the world will give them the support that they deserve and need. Do you think that is possible now?

CP: It’s really possible. Having Buddy really did focus the role of work in my life. I always say this: you can have it all if you don't try and do it all. Asking for help is the number one lesson in leadership – and I think in parenting and life as well. You can't do everything. But you can have a great job and a great life and a great kid and a great relationship. As long as you don't try and do it all yourself.

WF: I definitely can relate to that. You’re doing amazing things, breaking the glass ceilings, in your day to day life. Watching them shatter around you.

CP: I never accepted no for an answer. Once I was working and if where I was working couldn't feed my crazy ambition, then I’d just go and take it elsewhere. So, at Mother I wanted to run the biggest account, at BBH I wanted to run the biggest account, back at Mother I wanted to run the agency, back at BBH I wanted to run the agency, at Grey I got to run the agency. I was just always striving.

WF: How long have you been at Headspace and what have you seen in that time.

CP: I joined in 2018 at a time where we started going beyond eyes closed, guided app based meditation, to a space beyond the app. So I joined at a time when all of a sudden we were trying loads of new things, when the brand needed to be robust enough to stretch and flex into so many different spaces.

WF: And so what would you say the most important thing is now for Headspace?

CP: The mission is to improve the health and happiness of the world. It's written large on the walls, and we talk about it in most meetings. It is the first time I've ever worked with a brand which genuinely points everything at its mission. What we believe is that if you're going to improve the health and happiness of the world, you have to come in all sorts of different shapes and sizes, languages and voices, and on different channels for people who have different ways of getting headspace. For example, we realise there's only a certain number of people who are going to sit down three or four days a week and close their eyes for 10 minutes. Whereas to sit in front of Netflix for an evening is possible for hundreds of millions of people, or, for example, our Starbucks partnership – 100 million people buy a coffee from Starbucks every day. So how do we as a brand show up in that moment, and add value while they're waiting for their coffee? We aim to make this moment with their coffee even more enjoyable by adding some mindfulness to it. There is no part of Headspace I don't touch, from strategy to recruitment, to internal comms, to products, to events, to music, to animation, to TV shows, to podcasts. Partnerships are a huge part of my job. My role is to bring a creative point of view to the conversation and, I think, to push the ambition as far as we can.

WF: I guess Headspace has a long journey ahead of it because it's going to keep on developing and keep on becoming more and more important. Do you think you’ll need another side hustle?

CP: It's funny, Rich asked me a couple of years ago, maybe a year ago, ‘What does life look like for you after headspace?’ And I can't imagine. I think I'm going to be more and more committed to Headspace.
But my legacy, if I could be such a wanker as to say that word, is in unleashing the potential of the next generation of female leaders. That's what I'm interested in. I feel like I've been given the gift of this experience of growing into a creative leader, in an industry where there aren't that many female creative leaders. At Headspace I'm encouraged to make sure that I continue to build out my network of female leaders. I mentor half a dozen girls at Headspace. I sit on the board of OK Mentor, which is all about helping young girls break into the creative industries. So, when I do get more downtime, it will be put into the next generation of female creative leaders and unleashing the power of creativity in those young women. I feel so excited about that becoming more and more of my life.

WF: You've hinted at some good advice for the young woman who thinks, 'How on earth do I do that?' Things like 'Don't overthink it, follow your gut, don’t be scared, enforce boundaries.’ Is there something we’ve missed?

CP: I think it’d be: be really proud of your ambition and wallow in your ambition and live your ambition. If someone tries to stand in your way or clip your wings or push you down, just walk on by, take it somewhere else.

Image credits can be found here.