Kate Sheppard has worked in roles at DDB for more than 20 years, both in New York and Sydney. Following a well-deserved career break, she is now the managing director at Connecting Plots. Sheppard has built high-performing teams with an inclusive, values-driven culture where individuality is celebrated. She is a champion for diversity and an advocate for building a strong agency culture, exemplified at the Succulent Chinese Meal Supper Club, where creative thinking and collaborative ideas flow.
1. You’ve had a brilliant career from Ad Sales assistant at Vogue in the US, and now the MD of Connecting Plots. If you had to pick only one, what would be your career highlight so far?
Sheppard: Meeting IRL one of the OG Ds of DDB – the great Maxwell “Mac” Dane – when he came into the Madison Avenue office in New York for his 96th birthday celebration. I’m a sucker for living legends.
2. You have had extensive agency roles across a diverse category base, e.g., QSR, FMCG, airline, pharma etc. How has this client’s diversity informed your strategic perspective?
Sheppard: It’s definitely kept me on my toes and made me pretty adaptable. But the more categories I’ve worked across, the more I’ve noticed that while the context changes, people don’t. My approach always comes back to the same thing: finding the simple, human truth and using that to help people notice the brand, and hopefully give a damn about what it has to say.
3. I love that Connecting Plots has old school thinkers and new world dreamers. In reality, how does that work?
Sheppard: We’ve got a solid bench of seasoned practitioners – people who’ve seen a lot, made a lot, learnt from their wins and missteps, and carry a kind of resilience that only comes from experience. On the flip side, we’ve also got a collective of new generation thinkers who are curious, punchy, and completely comfortable working in undefined territory.
What’s great is the healthy tension that exists between the two. It’s when experience marries inventiveness that we find the most creative solutions to our clients’ problems.
4. As a young girl, what did you want to be when you grew up?
Sheppard: I wanted to be a businesswoman. Specifically, the type who walked through the airport with a wheelie bag looking glamorous and travelling the world doing ‘business’. This vision landed me in a business degree, later working in the fashion industry for a spell, and eventually travelling both here and overseas with my advertising career. So I reckon the younger me would say I’ve ticked that box.
5. How do I get in on the Succulent Chinese Meal Supper Club, and does this build agency culture?
Sheppard: It’s kind of like the speakeasy of clubs. A secret knock, a subtle wink, and then a dose of good luck. But once you’re in, let the fun times roll!
I think these dinners give a behind-the-scenes look into the sticky agency culture that Tom and Dave have steadily built over the years. You wouldn’t believe the curious conversations and unexpected creative collaborations that emerge when you put like-minded, experience-diverse people around a lazy susan.
6. As an industry, what’s one thing you would change to make us all better?
Sheppard: I would diversify who gets to create and who gets to decide. Despite increased efforts in recent years, our industry still struggles with systemic exclusion and homogeneity.
If we could build more equal hiring pipelines from the ground up, I reckon we’d set ourselves up to future-proof the industry for more authentic storytelling, and ensure decision-making rooms are not the monocultures they are today.
7. What’s keeping your CMO clients awake at night?
Sheppard: Timely question, given we just hosted CP’s annual Cannes Creative Review, which looked at exactly this, canvassing Cannes Lions case studies to test whether creativity actually managed to solve some of our clients’ problems.
Broadly speaking, it’s everything from vanishing attention spans to retailers pilfering more and more budget, performance media delivering diminishing returns, and AI rewriting the rules. It’s no wonder marketers are losing more sleep than ever. The only ones still catching a few winks are those who aren’t fighting the chaos, but playing in it.
8. Who have been your mentors, and what’s the best career advice you have been given?
Sheppard: I’ve had various bosses, clients, and colleagues whom I’ve counted as mentors over the years. But the soundbite I remind myself of often is from Marty O’Halloran, former global CEO of DDB Worldwide. He said, “The only difference between a CEO and an Account Coordinator is the size of the problem”. So I’m never far away from rolling my sleeves up and finding a better way.
9. What’s one thing that’s not on your LinkedIn profile?
Sheppard: I was on the first ever episode of The Gruen Transfer, selling the unsellable in The Pitch segment. We won… with Whale Meat, The Beef of the Sea.
10. Important last question, do your parents know what you do?
Sheppard: My mum technically knows I’ve been making ads for a while now, but her friends still ask her how I’m going at Vogue. ‘Devil Wears Prada’ trumps ‘Mad Men’, it seems.
