How Caroline Pay Brings Realness and Authenticity to the Advertising World

How Caroline Pay Brings Realness and Authenticity to the Advertising World

How Caroline Pay Brings Realness and Authenticity to the Advertising World

by Amanda Jaquin

A conversation with Dentsu Creative's Caroline Pay on her "real" approach to creativity, inspiration, and leadership throughout her dynamic career.

Caroline Pay is a creative visionary who knows the transformative power of real stories, real talk, and real life, and how they shape the future of both advertising and work. Caroline has played pivotal roles across agencies and brands alike — Mother, BBH, Grey, W+K, Headspace, and currently Dentsu Creative as CCO...the list goes on. Her career is more than a testament to her skills, but a reflection of her deep commitment to authenticity and meaningful connections.

We caught up with Caroline about creativity, self-care, and the importance of culture and community in her work. Plus, she shares her strategies for navigating a rapidly evolving industry and her advice for the next generation of creatives.
The Luupe: Caroline, you've been an incredible force within the advertising world — from leading creative at iconic agencies like Mother and BBH and now Dentsu, to steering Headspace's global brand and advising incredible mission-oriented brands like Flo Health! How do you adapt your creative vision and approach?
Caroline Pay: It all comes down to really believing in what I’m working on. Mother taught me to never compromise on authenticity, so I really have to drill down into what I’m working on to make sure I really believe in it, before I expect other people to. website in 2003
The Luupe: Could you share a behind-the-scenes story of a campaign you’re particularly proud of?
Pay: Even 20 years on, creating FRANK still remains one of my proudest career moments. Back in the early 2000’s, myself, my creative partner Kim (Gehrig, Director, Somesuch) and our CD Jim (Thornton, ECD, VCCP) had decided very early on that the answer to this telly ad brief was most certainly NOT going to be just a telly ad.
So after months of grafting, researching and selling in across multiple governmental departments, was born.
A nationwide drugs information service, available on the phone, online and on the ground, where young people could go and find out all they needed to know about drugs. This was a major shift away from ‘Just say No!’ campaigns of old, and towards a less judgemental and more informative approach, ensuring kids could make considered and informed decisions when it came to drugs. I am very proud to say that FRANK lives on to this day.
The Luupe: What’s your secret sauce for fostering a creative and collaborative environment, especially in a remote or hybrid setting?
Pay: In person matters! Having grown up in powerful cultures like Mother, BBH and W+K, I know from many years of experience that culture really feeds off proximity to one another. Water cooler chats, eavesdropping, sneaking an over-the-shoulder peak as you pass someone’s screen, awkward chats in the lift, over the kettle, on the way to the tube. My concern with fully remote work is that none of this happily accidental connection gets to happen. And now we have a generation of creative souls that haven’t necessarily felt that yet.
The Luupe: What inspires you?
Pay: Real life. Real talk. Real experiences. Real stories. Real feelings. Real connection, again.
I’ve always been a proper ‘high street’ creative thinker. Coming from Croydon, my cultural references remain pretty mainstream and I’m so comfortable with that.
I’m not one of those high-brow creatives, I’m afraid. Give me real any day of the week!
The Luupe: Given your past roles at Headspace, how do you see the intersection of wellness and creativity impacting the industry? What does self-care look like for you?
Pay: I think and hope that the old habits of working around the clock to prove you’re committed are long gone. These days people do seem to have more balance, more space, more permission to take a little more care of themselves and their mental health. That is one thing we did gain from the pandemic- more upfront realness outside of the office.
For me, self-care looks like very clear boundaries as to when I am working and when I am not. A four-day week. Immovable weekly therapy, with space to process after. I also love being in-office as the energy I get from being amongst my team works way better for me than being home alone and staring at a screen all day.
The Luupe: It’s clear you’re quite passionate about mentoring young women and new parents in the industry. Can you share a transformative moment or piece of advice you’ve given or received?
Pay: See the above! Boundaries are the key, especially as a returning parent. Set them, communicate them, repeat them and most importantly stick to them yourself- once you break them, everyone else will.
Other nuggets include bringing your whole self to work, speaking up in the moment, asking for feedback, and calling out unacceptable behaviours in the room. Oh, and never sit in the background, never offer to take notes/make tea. You deserve your seat at the table.
Headspace Brand Creative
The Luupe: How can brands stay fresh and relevant today without straying too far from their core identity?
Pay: Everything moves so fast these days, we must hold on very tight to our core values. Trying to keep up with everyone and everything it's very easy to swirl and lose yourself in amongst the noise.
We knew at Headspace we needed to really firm up our brand before we ventured outside of the app and into all other channels, other territories. Keeping our identity intact when collaborating with the likes of Amazon, Nike, Disney, Netflix could have been challenging, but I’m glad to say we remained true to ourselves wherever we showed up!
The Luupe: What emerging trends in advertising and brand storytelling are you most excited about?
Pay: I’m very happy to see humour coming back at last! All of those heart-string-pulling stories have had their time, and now we’re getting back to the lols!
We’re also making less and less expected/above-the-line work here at Dentsu Creative. Every project I'm seeing is coming to life in different shapes and sizes, which makes the job way more exciting and way more challenging in equal measure.
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The Luupe: What do you look for in a creative's work that makes them stand out for you to want to hire them? Whether a photographer, director, designer, or other talent.
Pay: For me, it will always be ideas first. Big, brave, simple, fresh thinking, no matter what the medium.
Second is their attitude- ambition, opportunism, empathy, optimism, confidence in their ability. And craft, I have the utmost respect for the detail-oriented people who take their craft to the enth-degree.
The Luupe: As a member of communities like the old girls club, can you share how community has impacted you personally and professionally?
Pay: I realised when I moved to LA quite how much I took my London network for granted! Community is huge for me. Especially because female CCOs are such a minority. Female creative leaders in general are such a minority. So communities such as OGC, Chief, OK Mentor, and the Whatsapp groups I find myself in are a huge support and inspiration.
The Luupe: Finally, what’s something you wish you knew when you started your career?
Pay: Not everyone will like you. Not everyone will like what you do, or how you do it.
So if you ever find yourself being misunderstood, undervalued, disrespected, or unappreciated, move on to somewhere that deserves you and the value you bring to the table.
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Amanda Jaquin
Amanda Jaquin is brand experience manager at The Luupe where she brings energy and ✨ to marketing, design, and community engagement. She lives in Kingston, NY, hates pickles, loves solving puzzles, and has a million tabs open right now.
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