In this special edition of Biz, Tech & Brains, we are joined by Chaluk Richards, recently appointed Head of Life & Health Insurance Business at GraceKennedy Financial Group. Until recently, Chaluk led GraceKennedy General Insurance, one of the Caribbean’s most trusted insurers—where his leadership drove remarkable growth. Chaluk is a thought leader – someone who offered us a revelation: about the true meaning of change, about building organizations that breathe humanity into every strategy, and about leadership that doesn’t just speak but shows up.
For us, this was more than an interview — it was an experience, captured here as faithfully as possible…
Krishna: Congratulations on your latest promotion, Chaluk, we’re so thrilled to have you here & can’t wait to see the man behind the excellence. We have noticed that GKGI has evolved massively under your leadership—with strong financials, digital progress, and customer focus.
So naturally, we want to start by understanding – what are your principles guiding this strategy and how do you make technology fit into it?
Chaluk Richards: Thank you for having me here, Krishna.
Our strategy is rooted in the Balanced Scorecard methodology— we flipped the usual focus on profit and revenue to put customers and employees first. When you get those right, results follow. It’s about the right people, with the right tools, doing the right things.
Insurance is sold, not bought — so products must meet both known and unseen needs. That’s why retention is such a focus for us; even our lowest-performing channel holds around 85% retention rate. It all comes down to one thing — customer empowerment. Technology plays a key role, but it’s never the hero — it’s the enabler so each time we design something new, we ask: does it help customers make informed decisions? Does it make insurance feel simpler, does it have the human-touch?
Because for too long, insurance has felt like an interruption — paperwork, offices, documents. We’re changing that, turning it into something seamless, intuitive, and valuable at every touchpoint.
Krishna: That’s wonderful, Chaluk. You emphasized customer empowerment as being central to your strategy. Yet, the protection gap is huge in the market— for example: out of 336 global catastrophe events in 2024; over half of the losses were uninsured. How can insurers leverage technology not just to improve experiences, but to bring protection to more people?
Chaluk Richards: You’re right, the protection gap is a major reality. In the Caribbean, a lot of it comes down to awareness — many people don’t see insurance as protection; they see it as optional. The reality? Most people are just one major illness or disaster away from bankruptcy. That mindset leaves them exposed.
This is where technology becomes transformative. It’s not just about smoother experiences — it’s about extending empowerment at scale. By leveraging both internal data and global datasets, we can understand the common risks and design solutions that truly protect them.
Predictive analytics, digital platforms, and targeted outreach let us reach more people, anticipate needs, and make insurance not just available, but meaningful.
Krishna: Rightly said. And from what we’ve seen, the Jamaican market seems proactive in expanding protection, with microinsurance legislation on its way — how are you leveraging this environment to reach the underserved segments?
Chaluk Richards: Yes, Jamaica has been ahead of the curve, and in fact, GK General is one of the few companies with a strong microinsurance portfolio.
We’ve been working closely with the regulator to pilot products ahead of the legislation — tailored for farmers, the self-employed, and the mass market. We’re also developing Cyber and GAP insurance, among other solutions.
These initiatives have taught us a lot about risks, customer behaviour, and what really works in underserved markets, and we’ve discovered that delivery channels are especially critical because microinsurance products are small and low-cost, and without the right approach, high administrative overhead can quickly make them unviable.
The key lesson for insurers is this: understand your market, test solutions early, and combine insights with technology because that’s how impact multiplies, and when you get the strategy right — how you design, price, and deliver — that is when microinsurance becomes genuinely far-reaching.
Krishna: That’s very insightful, good to see GKGI shaping the market.
You put deep emphasis on innovation & technology here, but we see that technology itself is evolving rapidly. Do you think the Caribbean industry is ready to embrace this— especially in combining humans and AI?
Chaluk Richards: Absolutely. My view on AI is similar to how we saw the Internet introduced — at first, we had to learn how to leverage it properly. AI is no different.
I don’t see it replacing the human workforce; I see it supercharging it. Think of communication: what once took weeks by letter now happens in minutes by email. AI does the same for insurance — it enables faster decisions, quicker responses, and frees people to focus on high-value work.
It’s about empowering people, not replacing them.
Krishna: What a wonderful perspective, Chaluk. With technology reshaping insurance, how open is GK to Insurtech partnerships while balancing core business and innovation?
Chaluk Richards: I believe every business should focus on what it does best. For us, that’s serving our insurance customers — it’s our core strength.
Investing heavily to build technology in-house often demands disproportionate resources, with little chance of recouping the investment. That’s why partnerships matter. Just as we work with audit and actuarial experts, technology partners are critical. By combining strengths, we can deliver real value whilst doing what we do best.
Krishna: Absolutely, the right partnerships are a critical part of any strategic initiative. That said, execution is the other side of the equation. How do you see strategy & execution working together to deliver results?
Chaluk Richards: I’ve always believed it has to be 5% strategy and 95% execution. A great strategy on paper means nothing if the organisation isn’t built to deliver it.
At GK General, once the vision is set, we redesign the organisation to make it real because strategy should never be static; it has to live and breathe through structure, people, and process.
It’s how every decision, every team, and every system works together to create momentum. When those align, execution becomes effortless — and results, inevitable.
Krishna: That’s a powerful point on aligning vision and execution, but some challenges arise despite the right measures. In your journey as a leader, have you faced such moments, and how did you rise above them?
Chaluk Richards: One challenge that many can relate to is dealing with rapid change— the onset of the COVID-19 was a clear example.
As a leader, the responsibility felt enormous — I needed to support customers while ensuring employees felt secure. To respond, we brought the right people together and accelerated decision-making, what used to take a month happened in a day. At the same time, we supported our teams’ well-being with weekly psychology sessions and offered customers flexible payments, extended repayment periods, and shorter-term policies to fit their budgets.
The result wasn’t just that we avoided layoffs or stayed profitable — it was that everyone felt seen and cared for. I think leadership isn’t about having all the answers — it’s about making sure the people who depend on you can keep moving forward.
Krishna: That’s incredible, Chaluk. Leading through tough times clearly tested your ability to make tough decisions. It feels like you continuously strive to be the best version of yourself, is that right?
Chaluk Richards: Yes, absolutely. I believe in getting better every day. After moments like COVID, we don’t just “go back to business”; we pause, reflect, and ask: What worked? What did we learn? What will we carry forward? Extraordinary times teach extraordinary lessons, so why not embed them into your being?
Early in my career, I decided that no matter the role, I wanted to consciously be a good leader. Most people receive technical training but very little guidance on leading — guidance that can create impact beyond work, touching lives. I chose to be a leader who helps people see themselves in the work they do. When they do, ownership sparks, creativity flows, and solutions come alive. That’s the true essence of learning & growth.
Krishna: Amazing…before we end, we have one final question, Chaluk. Your corporate journey has been wonderful — that aside, do you see yourself taking the entrepreneurship route? What is it that you, would like to do beyond what you have already been doing?
Chaluk Richards: That’s a great question. I’m focused on helping people achieve financial independence, which often ties to entrepreneurship. Recently, GKGI held an entrepreneurial showcase, which allowed our team members to share their personal business ventures and helped staff to see themselves not just as employees but as creators of their own future.
I’ve mentored small business owners and am working with a group of young men to build a learning ecosystem where ideas can grow before reaching the market, with real potential to impact lives.
At the same time, I’ve learned the importance of being present. Time is finite, and I’m focusing on what truly matters — family, meaningful work, and living with purpose, because the real measure is how fully you live and how much you help others live fully.
In the end, when people are allowed to be fully themselves, they own their purpose and destiny — and that’s what I want to spend my time nurturing.
Krishna: There couldn’t have been a better ending, Chaluk. Your journey shows that impact isn’t measured in numbers, but in the legacy you leave. Thank you for letting us witness that in action.
Want to know more? Reach us at inquisite@manomay.biz or biztechinsights@manomay.biz.
Biz Tech Insights Team Manomay
Disclaimer: The views and findings expressed in this material are for informational and educational purposes only. It is not intended as a guideline, recommendation, or substitute for any form of Professional (Consulting or Technology) advice. Under no circumstance shall we bear legal responsibility for using or relying on any information mentioned in this article. Unless otherwise specified, the views, case studies, and findings expressed herein are our own. The content displayed here is the Intellectual Property of Manomay Innsurtech Pvt. Ltd. You may not reuse, republish or reprint any of the aforementioned content without our written consent.
Sign up for our newsletters!