Cocktails With – Abigail Davis

Style Observer (SO): How would you describe Abigail in a few words?

Abigail Davis (AD): A true multi-hyphenate. A corporate leader by day, an MC by night, and in between, a mentor to young girls and community volunteer. I thrive at the intersection of it all because success means very little if it isn’t shared. Across strategy and the stage, my work is the same: Developing people and creating spaces where collective success is both achieved and celebrated. The next generation is watching, and I want them to see what’s possible when a woman refuses to choose just one lane.

SO: How was it co-hosting the Sagicor Corporate Group Awards?

AD: Electric. There’s a particular kind of energy in a room full of high performers who’ve worked hard all year and finally get to exhale and celebrate, and as a co-host, you’re the architect of that energy. You build it, you direct it, you decide where it peaks. It was also a privilege to share the stage with, and learn from in real time, an icon in the business, Jenny Jenny (Jennifer Small), who was nothing short of generous and encouraging throughout. What I took from the experience, even after years on the mic, is that growth doesn’t have a finish line. The ceiling keeps rising, and that’s the fun of it.

SO: Was this your first major gig?

AD: Not at all! I’ve been hosting for a few years now, across a wide range of audiences and occasions, mostly in the corporate space. I’ve held rooms of a few dozen and rooms of a few thousand, across corporate awards, media launches, seminars, panels, podcasts, and milestone anniversaries. Every major gig feels like the first in its own way, because the audience, the stakes, and the story are always different. That’s what keeps the craft exciting.

SO: What, in your opinion, makes a good host?

AD: Preparation you can’t see. A good host prepares; a great one overprepares and makes it look effortless. Everything underneath: the running order, the transitions, the contingency plans for when things go sideways, all these things must be worked out long before you hit the stage. Beyond that, genuine presence. You have to actually like the room you’re in. People can feel when you’re reading off a page versus when you’re in real conversation with them and engaging with something they’re clearly passionate about. And finally, service. Contrary to what one might think, the night is never about the host. It’s about the honorees, the brand, the moment. Your job is to create the space where everyone else shines.

SO: Changing gears now, your day job is financial analysis…
Were you able to sit with five accomplished business leaders, living or dead, who would they be and why?

AD: 1. Warren Buffett. My career began in investment analysis, and Buffett remains the clearest living example of what long-term, principled capital allocation looks like. I’d want to hear how he’s navigated markets through every major shift of the last half-century, and what he believes separates sustainable wealth from noise. That’s a conversation I’d want to take notes in.

2. Sun Tzu, The Art of War has shaped how leaders think about strategy for over 2,000 years, and I’d love to ask the man himself what he makes of modern corporate life. I suspect the principles hold up better than most of our quarterly frameworks.

3. Dario Amodei, co-founder and CEO of Anthropic. Anthropic is the company behind Claude, one of the world’s leading AI systems, and is widely recognised as a frontier lab in generative AI. I recently completed my MBA thesis on bridging the AI skills gap in financial institutions, and the research made one thing clear: The conversation around responsible, thoughtful AI adoption is the conversation of our time. Amodei sits at the centre of it, and Anthropic’s focus on building AI that is safe, steerable, and genuinely useful maps directly onto where I believe financial services needs to go.

4. Emma Grede. Founding partner of Skims, co-founder and CEO of Good American, and, simply put, a corporate baddie in every sense I align with. She’s built generational brands by spotting gaps no one else saw, moves with precision, and carries herself with the kind of confidence that reminds you excellence and elegance aren’t mutually exclusive. I’d want to learn how she protects her instincts while scaling at that level. Also, I’d like to know her skincare routine. For research purposes, of course!

5. Rihanna. The ultimate multi-hyphenate, and a personal north star for anyone trying to build a career that refuses to fit in one box. She’s a singer, actress, fashion designer, beauty mogul, and a self-made billionaire who has somehow made it all look easy. I’d want to know how she protects her creative instincts while running an empire, because that’s the balancing act anyone working across disciplines learns to live with. And honestly, I’d just like to say I had dinner with Rihanna!

SO: Were you able to fix a few pressing issues faced by the average Jamaican what would they be and what would your solutions be?

AD: First, financial literacy. Not at the “manage your daily expenses” level, but real fluency around insurance, investing and generational wealth-building. I’d make financial fundamentals a core subject at the secondary level, sitting alongside mathematics and english rather than an elective. More importantly, I’d pair the curriculum with mandatory, hands-on investment exposure through structured partnerships with financial institutions. Even a $100-a-week investment account per student would do more for long-term wealth-building than any textbook, because it would teach the two lessons that matter most: The habit of investing early, and the quiet, transformative power of compounding over time. Outside the classroom, I’d pair it all with strong community-facing programming, because financial literacy shouldn’t stop at school.

Second, the skills gap in a digital economy. My recent MBA research looked at how financial institutions are reskilling their workforces for AI, and the lessons translate directly home. The jobs our economy is creating are not the ones it used to create, and we need structured, accessible pathways for Jamaicans to meet that shift head-on, not in 10 years, but now. That means meaningful public-private partnerships, scholarship pipelines into high-demand fields, and practical certification routes that lead to real employment, not just aspiration. Upskilling can’t be a buzzword we use at conferences. It has to be an infrastructure we actually build.

SO: On a lighter note now… Which song are you currently obsessed with?

AD: I’m Getting Ready by Tasha Cobbs and Nicki Minaj.

SO: How would you describe your style?

AD: Elevated, intentional, and unafraid of colour. I lean into structured pieces as my foundation, like sharp blazers and clean silhouettes, pieces that mean business. Then I add one element that warrants a second look: A statement sleeve, a pop of colour or a bold shoe. I love a monochrome moment, but when the occasion calls for drama, I give it drama whether that’s a gown or a power suit!

SO: Heels or flats?

AD: Heels, most definitely!

SO: An evening in or out?

AD: Out. I love interacting with people and spending time with friends and family.

SO: What’s your preferred Appleton cocktail?

AD: Jamaican Daiquiri.

SO: Looking back, what advice would you give to 10-year-old Abigail Davis?

AD: You’re not too much. You’re just enough. The uncertain road is the path, so don’t let anyone convince you it isn’t. You’re going to try a lot of things: Stages, spreadsheets, classrooms and the boardroom and for a while it will feel like you’re supposed to pick one. You’re not. Every stop is depositing something you’ll draw on later, so collect generously. Keep saying yes to the rooms that scare you a little, because that’s usually where the growth is hiding. And remember: “The girl the world tries to shrink grows into a woman the world has to make room for. Trust her.”

SO: Share with us the title of the last book read.

AD: Walk Through Fire: A Memoir of Love, Loss, and Triumph by Sheila Johnson. She’s the co-founder of
BET and the first African-American woman billionaire. The book is a deeply personal account of reinvention at the highest levels. It landed for me at exactly the right time, because as someone building a corporate career and a creative portfolio, I’m drawn to women who’ve made reinvention look intentional rather than accidental. It’s a reminder that the women we now call icons were, at some point, simply women who refused to stay where life had placed them.

SO: Were you forced to pack up and leave Ja (in 24 hours) for an undisclosed destination, what would your travel essentials be?

AD: My passport and travel documents for sure. My full Apple ecosystem, because if I’m disappearing, I’m staying connected. Two versatile outfits that can take me from a meeting to a dinner to whatever the night decides, plus a swimsuit just in case. One classic nude pumps, one pair of sandals and my hot pink crocs. My on-the-go cosmetics bag, already packed and ready, because a woman should never have to think twice about her routine. My signature perfume that reminds me of home, so nowhere feels too foreign.

SO: Finally, what’s your personal philosophy?

AD: Work like it depends on you, trust God like it depends on Him and let excellence be the evidence.

Abigail Davis raises a Jamaican Daiquiri. toast Joseph Wellington

Appleton Estate Jamaican Daiquiri 2 oz Appleton Signature Rum 0.75 oz simple syrup 0.75 oz lime juice Joseph Wellington

Abigail Davis’s ultimate round table of accomplished leaders, living or dead, would include (from left) Dario Amodei, Rihanna, Sun Tzu, Warren Buffet and Emma Grede.

Words to live by….

Abigail Davis co-hosting the 2026 Sagicor Corporate Group Awards. LH Mulitmedia

Davis says her full Apple ecosystem.

…and her signature scent Burberry Goddess EDP are some of her travel essentials.

Davis was recently inspired by Sheila Johnson’s Walk Through Fire: A Memoir of Love, Loss, and Triumph.