Kaisy Mae O’Reilly is chief marketing officer of Stuart Weitzman
Introducing “Off the Cuff,” a new Q&A series from Luxury Daily exploring the career paths, current projects and next steps of those shaping the world’s best luxury brands.
The interviews feature a Proust-style twist, allowing readers to get to know industry leaders on a personal level. The tenth edition features Kaisy Mae O’Reilly, SVP, chief marketing officer at Stuart Weitzman.
In this Q&A, Ms. O’Reilly discusses kickstarting her career by working in beauty, the evolution of the luxury consumer's expectations and her passion for Stuart Weitzman's latest campaign, How Lovely to be a Woman, starring talents Aly Raisman, Christy Turlington, Issa Rae, Lucy Liu and Ming Xibe, among other topics. Here is the dialogue:
Serena Williams for Stuart Weitzman. Image credit: Stuart Weitzman
What was your first job ever? What did it teach you?
Growing up in the Philippines, my parents always told my siblings and I that the only inheritance we would ever get from them is our education, and that being a doctor or a lawyer was the ultimate career.
With an incredible amount of hard work, I got a full-ride scholarship for a highly selective medical education program. But as luck would have it, a graduation trip to Hong Kong totally changed the course of my life.
I was bitten hard by the travel bug, and all I wanted to do for the rest of my life was explore new places, immerse myself in different cultures and connect with people from all over the world. I ended up taking up Management Engineering and Economics instead with the hopes of one day becoming either a diplomat or a global executive.
Fast forward to my first job out of college, where I was the Country Assistant Brand Manager for the Personal Care and Cleansing division at Procter & Gamble. With almost two decades of my career at P&G revolving around the Beauty consumer, I have spent an inordinate amount of time trying to understand what women want, what drives hope and desirability and how we can translate those emotions into an actual purchase.
In the end, it’s not just about trying to make the sale at every touchpoint; it’s about how we can connect with her in her everyday context.
Which skills have been critical to your success? Did you gain these skills within or outside of the workplace?
Getting consumers to look at your brand differently or implementing big strategic shifts for your organization requires great storytelling. Whether the audience is your organization or the consumer, it’s important to first think about their context: what background conversations are going on in their mind?
What are their biases? This art of storytelling is about helping your listeners and viewers navigate through their thoughts and emotions, letting them experience and learn something so that they are changed at the end of it — hopefully positively, towards the outcome you are looking for.
Looking back, I probably honed my storytelling craft from years of brand marketing and thinking consumer-first at P&G, but I think this training really began much earlier. In school, I participated in extemporaneous speech and poetry reading competitions, which taught me a lot about projecting emotions through my voice to move the audience.
These experiences have taught me to put myself in my audience's shoes to better connect with them.
What is the best piece of advice you’ve ever received?
It’s actually two pieces of advice, which I call the two "Ps": People and Perspective. People make all the difference.
The biggest breakthrough ideas come when we invest the time to connect, listen and understand, agree or disagree, and dream together as a team. To have a team driven by a shared purpose makes all the difference.
And when things get tough, having a bigger perspective is what I find the most helpful. I try to always remember — or remind my colleagues — that a tough meeting or a tough day does not define who you are. T
here are many other things we should pay attention to and be grateful for, and sometimes it is okay to take a step back and remove yourself from difficult situations. Sometimes taking a moment to ground yourself with that bigger perspective is what you need to come back ready with a solution.
How has your field changed since you started out in luxury, and what do you think your industry will look like in a decade?
Whereas luxury was previously considered a badge of achievement for consumers, these days, the consumer’s preference has evolved to prioritize an experience that is much more personal.
Recently, I’ve noticed brands go through periods of introspection as they take more pride in their heritage and double down on the customers whose beliefs align with their own. As a result, the relationship between the brand and consumer is a lot more considered and truly a reflection of who they are.
I love this era of brand-building. At Stuart Weitzman, for example, creating stylish and comfortable shoes that empower women with strength and confidence is the cornerstone of our brand.
Now, more than ever, is an important time to stand strong as a woman, so we have carefully chosen our latest global ambassadors to be the embodiment of this strong feminine spirit. Looking ahead, the beliefs and values of a brand and what it stands for should not change much — if at all.
Instead, it’s about how brands can effectively reach their consumer that defines the industry. The pace of digital innovation is so astounding to me that it is almost not useful to predict what it could look like in the near future.
Instead, the focus now should be on building the skills to navigate this future — for instance, being able to adapt to change.
What recent projects have ignited your passion for working in luxury?
I’d have to say our “How Lovely to Be a Woman” campaign film, which premiered just recently on September 4th.
I challenged my team to break the category language, to go beyond the traditional fashion campaign and rethink our approach to selecting our global ambassadors and telling their stories. With this campaign, we’re shining the spotlight on the SW woman through our cast of strong, confident, multi-hyphenate women.
A film starring the talents premiered Sept. 4. Image courtesy of Stuart Weitzman/Ned Rogers
Like Aly Raisman, Christy Turlington, Issa Rae, Lucy Liu and Ming Xi, our customer is the woman who does it all: career, family, hobbies and passions, and through everything, she pushes forward — and she does so in style. Our campaign is a celebration of what it means to be a woman today, the perseverance and strength it entails, and a celebration of how lovely, indeed, it is to be a woman.
I’ve always believed in doing good with one’s platform, and with our platform here at Stuart Weitzman, we are continuously striving to make a difference in our customer’s life, to inspire her to feel a little more confident each time and to feel like she can do everything she sets her mind to. Because she can.
Who, in any industry or sphere -- corporate leader, philanthropist, motivational speaker, celebrity, etc. -- would you most like to share a long lunch with and where would you take them?
I would love to have a long lunch with travel novelist and nonfiction author Pico Iyer. Reading his work always transports me to new places, not only in the literal sense of a new location to learn about, but it also never fails to make me wonder, learn something new about myself and find a level of connection to a subculture in some other part of the world.
I can just imagine this conversation with Pico being such a respite and one that I will always remember to take me out of the chaos to a calmer, quieter place where I can remind myself to have that bigger perspective on life I spoke about earlier. I would probably take him to a local diner near where I live, and we’d continue our conversation as we take a walk at a nearby park!
How do you get into the right mindset before a big meeting or presentation?
Preparation leads to confidence. Knowing I have spent enough time preparing, practicing and socializing the content, I’m able to trust myself to deliver the presentation well.
I remind myself that I was given the opportunity to speak because I’m the most qualified person in the room. I am an expert on the subject matter and have earned my right to be at the podium.
Then it’s simply about delivering what I already know.
On your days off, what can you be found doing to relax or have some fun?
I love to host and entertain, and my house in New Jersey is in a constant state of reinvention, depending on the season or the holiday we’re celebrating.
At night, I also try to sneak in time to read — sci-fi and fantasy are my two favorite genres. They help clear my mind of the present and help me imagine possibilities.
What does luxury mean to you?
To me, luxury extends beyond aesthetics or functionality. It is a deeply personal experience in that it can trigger an extraordinary range of emotions within the receiver.
But in the long term, true luxury is the alignment of values and belief systems that make one feel like a part of something bigger. At Stuart Weitzman, we create shoes that empower the modern woman to stand stronger, to step confidently forward, to look and feel her best so she can take on anything that comes her way.
Being inspired with confidence — that’s what luxury truly means to us as a brand.
Whether a product or service, what is your favorite luxury indulgence?
I go back to where it all started: Traveling with my family. Being able to visit new places with my husband and two kids, with our busy schedules, is an indulgence.
Tokyo, towards the end of fall, is next on our list. We’re also big fans of the Disney Parks, and as DVC members, we vacation there at least twice a year!
My family and I look forward to these vacations — we love being transported to new worlds and experiencing new things together!