I’m thrilled to sit down with Simon Glairy, a leading voice in the insurance and Insurtech space, whose expertise in risk management and AI-driven risk assessment has reshaped how we think about innovation in the industry. With a deep commitment to diversity, equity, and inclusion, Simon brings a unique perspective on how these principles intersect with business success. In our conversation, we explore the cultural barriers holding back diverse talent, the evolving definition of leadership, the power of belonging as a driver of performance, and the importance of supporting underrepresented groups like transgender and neurodivergent employees in the workplace.
How do you see the rigid culture in the insurance industry impacting the rise of ethnic talent into leadership roles?
The rigid culture in insurance often acts as a gatekeeper, prioritizing conformity over diversity of thought. It’s not just about explicit bias; it’s the unspoken rules—how you’re expected to look, speak, or network—that can sideline ethnic talent. I’ve seen incredibly skilled individuals passed over for promotions because they didn’t fit the traditional mold of what a leader “should” be. This rigidity stifles innovation and sends a message that only certain backgrounds belong at the top. Breaking this cycle means challenging norms, like outdated dress codes or rigid hierarchies, and actively creating pathways for diverse voices to be heard.
What shifts are you noticing in the qualities valued for leadership within the sector, and how can companies nurture these traits?
Historically, leadership in insurance was about projecting unshakeable strength—think bold, Superman-style traits. But there’s a growing appreciation for what I’d call Clark Kent qualities: empathy, vulnerability, and a willingness to listen. These traits build trust and foster collaboration, which are critical in today’s complex environment. Companies can nurture this by rewarding emotional intelligence in performance reviews, offering mentorship that emphasizes soft skills, and creating safe spaces for leaders to show their human side without fear of judgment.
In what ways can insurance companies better support transgender employees and create truly inclusive workplaces?
Supporting transgender employees starts with tangible actions like employer-backed healthcare that covers gender-affirming care—it’s a powerful signal of commitment. Beyond that, it’s about culture. Genuine allyship means educating staff to dispel myths and fostering an environment where trans colleagues feel safe to be themselves. I’ve seen companies host workshops or bring in advocates to share lived experiences, which can transform perspectives. It’s not just about policy; it’s about day-to-day interactions that affirm someone’s identity and worth.
Why do you think belonging is being recognized as a key driver of performance in the insurance industry?
Belonging isn’t just a feel-good concept; it’s a business imperative. When people feel they belong, they’re more likely to innovate, take risks, and stay resilient through challenges. I’ve worked with teams where a strong sense of belonging led to groundbreaking solutions because everyone felt safe to contribute ideas. Without it, you lose engagement and talent. Belonging turns a workplace from a transaction into a community, and that directly impacts the bottom line through better retention and productivity.
How can companies help employees, especially those returning from maternity leave, feel a stronger sense of belonging?
For employees returning from maternity leave, belonging hinges on flexibility and trust. Offering adjustable schedules or remote work options shows you value their whole life, not just their output. Recognition is equally important—managers should celebrate their return, acknowledge their contributions, and involve them in meaningful projects. I’ve seen simple acts, like a personalized welcome-back plan, make a huge difference. It’s about ensuring they don’t feel sidelined but instead see a clear path to thrive.
What does belonging mean to you personally in the context of this industry, and how have you seen its absence affect teams?
To me, belonging in insurance means feeling valued for who I am, not just what I deliver. It’s about knowing my perspective matters, even if it’s different. I’ve witnessed teams crumble under a lack of belonging—morale drops, turnover spikes, and creativity stalls. One instance that sticks with me is a colleague who left because they felt invisible; their departure cost the company not just talent but institutional knowledge. Companies can counter this by fostering open dialogue, celebrating diverse identities, and ensuring everyone has a seat at the table.
How can neurodivergent individuals turn their unique perspectives into strengths in the workplace, and what support do they need to succeed?
Neurodivergent individuals often bring unparalleled strengths—think outside-the-box problem-solving or intense focus—that can be game-changers in insurance. I’ve seen colleagues excel at spotting patterns in data that others miss, purely because their minds work differently. But they need environments that play to those strengths: clear communication, sensory-friendly spaces, and managers who adapt rather than enforce a one-size-fits-all approach. Support systems like mentorship or tailored accommodations can unlock their potential and benefit the whole organization.
What’s your forecast for the future of diversity and inclusion in the insurance industry over the next decade?
I’m cautiously optimistic about the next decade. We’re seeing real momentum—more companies are prioritizing diversity not as a checkbox but as a core strategy. Technology, like AI, could help reduce bias in hiring and promotions if used ethically. But the challenge will be sustaining this beyond surface-level efforts. I predict we’ll see more focus on intersectionality, addressing overlapping identities, and a push for measurable outcomes over vague promises. If we get it right, insurance could become a model for how tradition and inclusion can coexist and drive success.
