Cocktails With
Kiran Kerr
PBS Group Head of Regional Marketing & Corporate Affairs, Caribbean
Style Observer (SO): How would you describe Kiran in a few words?
Kiran Kerr (KK): I would say collaborative, optimistic and a bit of a problem solver. But I thought it best to ask the people around me for the real answer! They said inclusive, supportive and someone who pushes for the best, while also encouraging them to think things through, come up with a plan and take ownership on the way forward.
SO: What are your non-negotiable/s as an executive?
KK: Integrity, respect and accountability. I believe you can demand timely, quality work without losing sight of how you treat people. Clear communication is also important to me: Be upfront, set expectations, follow through on what you say you’re going to do and when you get something wrong, own it. I value honesty in all aspects of my life, not just at work.
SO: Which five executives living or dead, male or female, would you invite to a company retreat?
KK: Rihanna: She took the influence she built through music and turned it into a business empire. I find it interesting how she made inclusivity part of Fenty from the beginning, expanded the brand into different product lines and then knew when it was time to hand over the day-to-day role and move into the executive chair role. I’d love to hear how she has approached each stage of that growth while keeping the brand authentic to her.
Tim Cook: Taking over Apple after Steve Jobs must have come with an incredible amount of pressure and expectation. He stepped into a company so closely associated with Jobs, knowing that every decision would be compared to what came before. He’s just ended his time as CEO and looking back, he clearly created a legacy of his own, growing the value of the business and launching new products. There’s a lot to learn from how you take on something with such a strong legacy, lead it your own way and ultimately make your own mark.
Jessica Alba: I like that the idea for The Honest Company came from a real problem in her own life, and that she then had to work hard to get people to take her and the idea seriously given her background. She spent years pitching the business, learning the industry and backing herself with real data. But she also knew where she needed expertise and surrounded herself with people who had it. There’s something to be said for not needing to know everything yourself. If you build the right team around you who can fill those gaps, you can still build something really successful.
Kristina Kerr: My sister, who co-leads a small communications agency in Jamaica. I have always admired the resilience it takes to build and sustain a business of your own, particularly in an industry that is constantly changing. In a smaller business, you have to wear many hats, from leading a team to managing clients, finding new business and still making sure the work gets done. I would want her at the table because she brings a very different perspective on leadership and entrepreneurship, and because I know she would ask the questions no one else would.
Thalia Lyn: I admire what she built with Island Grill. She took an idea that was rooted in Jamaica and created a brand that has been able to compete with international players. I would love to hear about the decisions behind that growth, especially since it was not always a straight line, the lessons learned along the way, and what it really takes to build and sustain a successful business in Jamaica. And honestly, I’m sure a lot of people would love to know how she has managed to balance the demands of building a business and her community work while still having a full personal and social life and always looking fabulous while doing it.
Five executives living or dead, male or female, that Kerr would invite to a company retreat? (From left): Tim Cook, Jessica Alba, Thalia Lyn, her sister Kristina Kerr, and Rihanna.
SO: Do please share with us the last business feature you read.
KK: I read an opinion piece in Inc. about why businesses sometimes struggle to successfully introduce AI into the workplace. It looked beyond the technology and training and focused more on the cultural foundation needed to bring teams along on the journey. We talk a lot about what AI can do but getting people comfortable with it, helping them understand how to use it properly and where it can add value is just as important. I see it in marketing too. There can be an expectation that you simply put something into an AI tool and it will create exactly what you need, but you still have to know what you’re trying to achieve, give it the right direction and apply your own judgement to what comes back.
SO: You have travelled extensively throughout the Caribbean. Which country would you give the nod to for ease of conducting business?
KK: That’s a tough one. Every Caribbean market has its own nuances, and I have learnt that what works in one may not work in another. Doing work across the Caribbean is really about understanding the culture, how people operate, and the relationships that exist. Once you understand that, then navigating becomes easier.
SO: What’s your take on imposter syndrome? So many women speak to this as a real challenge.
KK: I’ve definitely experienced it, especially when I’m stepping outside of my comfort zone and taking on something new. That’s usually when the self-doubt creeps in, and I start questioning whether I know enough and if I’m really ready. Interestingly, it came up on a podcast I was listening to recently, and they were talking about how, growing up, we’re often taught to care about what people think. And while that isn’t necessarily a bad thing, overthinking it can sometimes lead us to second-guess ourselves and our capabilities.
When those moments come, I try to remind myself that I’ve gotten to where I am because of the work I’ve done and the experiences I’ve had. But I also remind myself that none of us knows everything. We’re always learning, and sometimes being a little uncomfortable is needed to grow in what we do.
SO: How would you describe your executive style?
KK: I’d say simple and understated. I tend to gravitate towards neutrals like navy, black, brown and white, with gold jewellery and tailored pieces. You’ll usually find me in a pair of tailored pants and heels.
SO: What’s your take on the adage: “Dress how you wish to be addressed”?
KK: Maybe it’s the marketer in me, but I think how we dress is part of the story we tell about ourselves, depending on who we will see, where we are going and how we want to be seen. And my mother always told me to make sure I put myself together, so I’ve always been conscious of how I present myself. Of course, what you wear is only part of it. How you carry yourself and the confidence you bring are just as important.
SO: What are your handbag essentials?
KK: My Phone, Fenty lip gloss, Altoids and my card case.
Kerr’s handbag essentials? Phones, Fenty lip gloss, Altoids and card case. (Photo: Gavin Jones)
SO: Share with us a few of your creature comforts.
KK: A bowl of noodles, a good workout, a heavy duvet and a glass of wine at golden hour.
SO: What are you drinking today?
KK: An Appleton Estate Rare Honey Soother.
Appleton Estate Rare Honey Soother 2oz Appleton Estate 12-Year Old Rum 10z honey 1/2 oz lime juice (Photo: Gavin Jones)
SO: An evening in or out?
KK: Depends on the day! Sunday to Thursday, an evening in is non-negotiable. Come Friday, I’m ready to head out.
SO: Heels or flats?
KK: Heels. Anyone who knows me knows I’m probably showing up in an extremely high pair!
SO: Concert tickets for Olivia Dean in NYC or Celine Dion in Paris?
KK: Celine in Paris, because it’s Paris.
SO: Finally, what’s your personal credo?
KK: Do good work, treat people well and enjoy life!
Sip, sip! (Photo: Gavin Jones)