Women don’t ask for promotions as often as men, and as founders, face more stringent questioning from investors about their end goals, according to a group of expert panelists moderated by Insurtech Insights USA President, Megan Kuczynski.
The Women’s Leadership Congress, which recently took place at Insurtech Insights USA 2024 in New York, saw Sabrina Hart, President and CEO of Munich Re Specialty Insurance, Casey Kempton, President, Personal Lines at Nationwide and Margeaux Giles, CEO and Founder of Irys discuss a range of topics related to female advancement in the insurance industry.
Women need more confidence when it comes to remuneration
According to Kempton, who has extensive experience in managing large teams, women simply don’t push for pay rises as often as their male counterparts – and as a result, can often end up being underpaid and feeling disenfranchised.
She told a packed, mainstage audience: “If you’re a woman, you might notice that men frequently ask for raises. In my experience managing both men and women, I’ve never had a woman ask me for a raise, whereas every year there are always three or four men who approach me asking about promotions and higher pay.”
“As a woman, I’ve often faced more intrusive questions. For instance, I’ve been asked if I’m still married to my husband after achieving business success.
Margeaux Giles, CEO and Founder of Irys
Kempton said she didn’t like to generalise when it comes to the sexes, but that after managing people for many years, she’d “observed a significant disparity” between the genders when it comes to requests for a pay rise.
“I’ve often had to encourage women to reflect on their satisfaction with their bonuses, to consider if they received a raise, and to recognise that they deserve it. I’ve urged them to ask for what they deserve, which is a challenging skill to develop. Society doesn’t teach us to have the kind of confidence that says, ‘I just deserve it.’ I believe women should cultivate that confidence to level the playing field.”
Sabrine Hart, agreed with Kempton and said her own personal experiences echoed that. She went on to say the personal confidence in the workplace – and understanding that valued skills rather than inflated expectations, was key in encouraging female promotions.
“Reflecting on our earlier conversation, I do notice a difference in confidence levels, especially early in careers. It’s often said that women feel they need to be 100% ready for a role before they pursue it,” Hart said.
She continued: “I experienced this myself when I was first asked to move from a profit centre role to a CUO position. Despite my high confidence in my previous role, I resisted the move. It took my manager’s encouragement to make me realise that I didn’t need to manage all the products myself—there were capable people for that. Instead, he emphasised the transferable skills I could bring to the role, which ultimately gave me the confidence to make the transition.”
Female founders also face more scrupulosity from investors
As well as a lack of confidence in corporate roles, female founders face more stringent conversations about their business ideas and ROI expectations from investors, said Margeaux Giles, who spoke about her own journey as an entrepreneur and insurtech startup leader, during the panel.
She said that the founding space is already extremely challenging, even for experts in their field – but that being female adds an additional layer of complication. “When building a business, you hopefully have some expertise, proven product-market fit, and you’re seeking funding. Confidence plays a huge role here, particularly in asking for what you’re worth. Presenting a business proposition that could involve tens of millions of dollars can be daunting.
I do notice a difference in confidence levels, especially early in careers. It’s often said that women feel they need to be 100% ready for a role before they pursue it,”
Sabrina Hart, CEO, Munich Re Specialty Insurance
“As a woman, I’ve often faced more intrusive questions. For instance, I’ve been asked if I’m still married to my husband after achieving business success. These types of questions seem aimed at doubting my commitment and capabilities. I’ve also been asked for more documentation and proof than my male counterparts. It’s frustrating to see that male founders, even those with multiple failed ventures, continue to secure funding at higher levels.”
Giles noted that the disparity made her realise the importance of confidently asking for money and setting boundaries. “When investors cross the line, it’s crucial to recognise that they are bidding to own a part of your company. Shifting my perspective from seeking investment to evaluating investors—as if they were potential partners in a relationship — changed how I was treated. I started seeing investors as having to prove themselves worthy of being on my cap table, which made a significant difference in the dynamic.”
She said the mindset shift was a game-changer, because she saw her worth to the investor, rather than the other way around – and was prepared to walk away if the deal wasn’t good enough. “In situations where you’re asking for a raise, it’s crucial to be prepared to take a stand if you’re met with resistance or discomfort. If your request is denied or not taken seriously, you need to be brave enough to say, “I’m leaving.” Recognise your worth and be willing to find a place that values you without having to go through an exhausting process just to get what you deserve.”
Pathways to leadership
Focusing on results and continually moving forward are important ways to ensure women don’t get left behind, said Hart, as she responded to a question about what advice she would give her 25-year-old self climbing the corporate ladder. “Reflecting on practical advice, I’d tell my younger self to learn a second language early on; waiting made it more challenging. Aligning with what Casey mentioned, I’d also advise not to sweat the small stuff.”
She continued: “Early in our careers, we tend to worry about minor issues and anticipate worst-case scenarios, most of which never materialise. Another crucial piece of advice would be to focus on delivering results early—it’s incredibly beneficial. Lastly, an essential leadership and management lesson is not to delay tough decisions. Procrastinating won’t make them any easier.”
Instead of lamenting these challenges, navigate them. Don’t let them erode your sense of self. Be proud of who you are and what you’re learning, and don’t let anyone tear you down.”
Casey Kempton, President, Personal Lines, Nationwide
Kempton concluded: “Particularly as young women, we don’t always receive positive feedback. Questions like, “How do you know that?” or “How come you think that?” often challenge our intuition, making confidence seem like a double-edged sword. It’s essential to maintain confidence without letting doubt erode it, despite these subtle challenges.”
She added: “I’d advise my 25-year-old self to be resilient in the face of being ignored, having your hand unshaken, or being mistaken for the secretary instead of the boss. Learn to shed these experiences like Teflon. Be prepared for interruptions; it’s a reality of our world.
“I’d emphasise not personalising these interactions—they are part of our culture, not a reflection of your worth. Instead of lamenting these challenges, navigate them. Don’t let them erode your sense of self. Be proud of who you are and what you’re learning, and don’t let anyone tear you down.”
Reporting by Joanna England
