Diversity isn’t a side initiative - it’s a business imperative. Yet in insurance boardrooms, representation still lags behind rhetoric, and progress is mistaken for parity.
Even as insurers champion risk mitigation and resilience, their leadership remains overwhelmingly white and male. Women make up 59% of the general insurance workforce - but only around 22% hold C-suite roles. For women of color, the numbers are starker: just 3% in the C-suite, and only 2% on boards. Despite making up the majority of the industry’s talent pipeline, women remain underrepresented where decisions are made - and where change can actually happen.
Margaret Resce Milkint (pictured), global insurance practice leader at Diversified Search Group, has spent over three decades pushing for systemic change. For her, this is more than a DEI talking point - it’s about embedding inclusion into the DNA of organizations, fostering executive sponsorship, and redefining what it means to lead in modern insurance.
“None of this happens by accident. So having the intentionality, having the purpose and the commitment - that has to come from the board,” she said.
While she acknowledged that the industry has moved forward, Milkint was quick to point out that progress alone doesn’t equal equity.
“There is a gap,” she said. “But there’s also been great movement. We've got a lot more work to do, but we can't neglect the fact that we've made some strides.”
She recalled a time when “maybe there was a handful of women.” Now, she sees more women in C-suites and boardrooms - but the numbers still fall short.
To accelerate momentum, she argued, commitment must be vocal and collective.
“I like the idea of the noise, because the noise reflects the change,” Milkint said. “When the industry comes together and says, ‘This is how we want to grow, how we want to evolve,’ that makes a difference.”
She sees this shift as an ecosystem - one where shared progress matters more than individual wins. “We’re in an ecosystem together. Collective industry success is what’s important,” she said.
That means setting aside branding and competition and locking arms across companies and sectors to move forward together.
This vision for change isn’t purely top-down. It’s personal. “Making it personal is also important, because we can affect change. We can't wait for other people to do it for us,” she said.
That grassroots momentum, she added, is being powered by women’s groups and industry networks that prioritize community over competition. “Each celebrating each other, not in competition, but in that spirit of community.”
Even so, Milkint cautioned against a common and dangerous misstep - treating inclusion as a bonus rather than a baseline.
“The misstep, if I could generalize it, is not having awareness of the impact and upside of inclusivity in culture,” she said. “That’s when the inclusion, the belonging, the welcome are off to the side and not embedded into the very culture, the very DNA of an organization.”
When inclusion is fully embedded, the effect is transformative. “That’s when it sings in an organization, because then all the voices are heard,” she said. “It’s not off in a silo.”
To ensure meaningful progress, Milkint believes companies must rethink how they develop and elevate talent. Mentorship alone won’t get women and professionals of color into the C-suite. Executive sponsorship is equally critical - and both must be deliberate.
“Mentorship and executive sponsorship are very different, but they go hand in hand,” she said. “Mentors work side by side with their mentee, and they create that bond.”
She described insurance as an “apprentice business,” where future leaders are shaped through proximity and experience. “You learn at the side of another underwriter, actuary, claims professional,” she said.
But beyond technical skill, she emphasized the importance of cultivating gravitas - a quality often perceived as innate, but one she believes can be learned. “Gravitas embodies trust and respect and caring and confidence - all the things that we as an industry are looking for in the modern leader.”
To Milkint, redefining leadership isn’t about lowering standards. It’s about expanding what leadership looks like.
“Leadership requires great focus on technology and financial acumen and data drive, but you have to be able to blend that with the human skills that are equally important.”
