The gendered glass ceiling

Women’s equality in the insurance and financial services industry has come a long way, with nearly half of entry-level positions held by women today.

Still, top women in the field say there’s more work to be done, as only a handful of women in the industry ever make it to the C-suite level despite being just as capable as their male counterparts. 

“I think the glass ceiling looks different than it did 20 years ago, but I would say, in many ways it still exists,” said Michelle Youshock, head of personal lines at World Insurance Group. 

“It’s less overt, it’s more subtle, but it shows up in who gets the stretch assignments, who gets revenue-driving roles, who’s invited into the strategic conversations. I’d say we’ve made a lot of progress — we see women leading divisions, practices and national initiatives. But we’re still struggling to see representation at the highest decision-making levels.”

Gemma Ros, chief technology officer at The Zebra, is one of the many women executives who say the gap is a symptom of something more systematic — a repeated pattern of underrepresentation that should be addressed. 

“The difference that I’m seeing now versus when I first started is fewer overt barriers. Instead, what I’m seeing are more patterns. There’s just systematic under-representation in technical leadership. There are fewer women in profit-and-loss ownership roles, fewer women in CEO pipelines,” Ros said.

And they’re not alone. Of the five women InsuranceNewsNet spoke with, all agreed that a lack of women in the highest career positions has become an elephant in the room that needs to be addressed.

‘Set back from the beginning’

According to the 2025 “Women in the Workplace” report published by the Lean In Foundation and McKinsey & Co., gender equality in the workforce steadily dwindles at each consecutive level.

Most notably, there is what Mary Noble-Tolla, director of research and content at the Lean In Foundation, describes as a significant “drop-off” or “broken rung” for women, beginning at the very first level of career progression.

“What we found over the last 10 years is that the biggest drop-off often isn’t from vice president to C-suite; it’s actually from entry level to manager. There was a tremendous drop where women are not getting promoted out of entry-level roles into manager roles, and that sets them back from the beginning,” Noble-Tolla said.

Lean In’s data shows, for example, that at the entry level, men hold about 32% of roles compared with 28% held by women. Just one level higher, at the manager stage, the gap widens.

That trajectory continues. In the finance industry specifically, the percentage of women in managerial roles goes from around 46% to 38% at the next step up, directors. Eventually, only 27% of women ever reach the C-suite. 

“We call it the broken rung because if you imagine career progression as a ladder, the first rung is broken for women. And then when you look at women of color, it’s even more broken,” Noble-Tolla pointed out.

“It doesn’t just drop off before the C-suite or before leadership — it drops from entry level to manager, it drops from director to VP, it drops from VP to senior vice president and it drops from SVP to C-suite, and that’s been true for the last 10 years.”

A complex cause

For those with personal experience and for researchers, the gendered career gap is a complex issue with multiple possible causes — and solutions.

Lean In’s research suggests “flexibility stigma” is a major factor. It found that women working from home are assumed not to work as hard as men who work from home and that women who work remotely three or more days per week were 50% less likely to get promoted.

“Some companies are rolling back flexible work, and that impacts women more because women tend to be caregivers more than men. It looks like women are being held back by flexibility stigma. That’s the bias women face far more than men when they can use flexible working arrangements,” Noble-Toller explained.

Additionally, the report found that women, especially at the entry level, tend to receive “far less career support” than men despite having the same level of ambition. For example, they are often given fewer leadership training opportunities.

The research aligns with what leaders like Andrea Hecht, chief financial officer at CSAA Insurance Exchange, have found to be the case as well.

“I think, ultimately, it comes down to getting people access to things that are going to put them on the right trajectory to get to that C-level early on in their career. Things such as P&L responsibility, getting assigned to super-visible projects, and I think that it’s one of those things that if you’re not thinking about it intentionally, it may not happen organically,” Hecht said.

On the other hand, many women leaders also believe there’s a cultural tendency for women to unintentionally sell themselves short in the workplace. 

“Generally speaking, I think women are less likely to advocate for themselves. They’re going to wait until somebody comes to them, but you must advocate for yourself,” Angie Welsh, founder and agent at My Annuity Agents, said.

Breakthrough

Identifying the “why” is only part of the equation, however. A bigger question is how equality can be achieved — and Ross believes the answer is less about a dramatic shattering of glass and more about consistent disruption of the status quo.

“For me, breaking the glass ceiling right now is less about making this big, dramatic smash, but more about systematically redesigning how these opportunities are being distributed,” Ross said.

“Where I see the bigger challenge now is not so much around access as it was before when I first started, but it’s really about sponsorship and advocacy. It’s ensuring that women are allowed to fill stretch roles, that they’re given visibility into high-priority and high-impact projects, and that they’re supported when they take calculated risks.”

Diane Delaney, executive director of the Private Risk Management Association, called for more intentional efforts to place women in the highest decision-making roles in the industry.

She said this is something her board has made an extra effort to achieve, with results that have led to richer engagement for the organization.

“I’m hopeful that this is starting to change, but it was intentional. It’s being intentional about how we’re reaching out to high-potential female leaders within our organization and encouraging them to apply for this position or mentoring them,” Delaney said.

Mentorship and women advocating for other women are a huge part of the equation, as almost every executive shared their personal experiences with getting to their position with the help of the leaders who came before them. 

For Youshock, that journey started at home. 

“I have been blessed with a mother who pushed the glass ceilings in the 1980s. She was corporate America, climbing the ladder, leading the charge and showing me how it was done. Representation matters,” an emotional Youshock said as she held back tears.

“I want to be that for others. It’s just super important to me. We must invite them into the room. We must say, ‘Hey, let’s bring you into where the conversations are happening and the decisions are happening.’

Rayne Morgan is a journalist, copywriter, and editor with over 10 years' combined experience in digital content and print media. You can reach her at [email protected].