Women in Insurance Live returned to Chicago on September 16, and this year’s edition was the biggest yet. More than 500 attendees packed the Fairmont Chicago for a full day of panels, networking, and hard conversations about where the industry is headed, while the afternoon before the main event saw 200 leaders set sail on an architectural cruise along the Chicago River, trading skyline views for candid, off-the-record talk ahead of the main program.
A day built on honesty and momentum
From the opening session, one theme carried through nearly every conversation on stage: leaders don’t always have complete information, and the job is to move forward anyway. Katie Flynn, Chief Financial Officer at Safety National, set that tone early. “We don’t always have all the information we need to make a decision, and we do the best we can with what we’ve got,” she said, pointing to clear communication and transparency with stakeholders as the anchor for navigating that uncertainty.
That appetite for candor extended to the industry’s relationship with artificial intelligence, a subject that touched nearly every session on the agenda. Marie Fay Molina, Partner and EVP of Revenue at C3 Risk and Insurance Services, described a room grappling openly with the fear that often accompanies transformation..” We’re all still learning, still wanting to share best practices on how to tackle complex problems like talent retention. In this war for talent, how do we retain and attract our best people? How do we work with change management and transformation in the age of AI? That’s been a very common theme throughout the day. And then also, how do we continue to mentor and support the next generation of talent?”
Jody Kaufman Davis, Co-President of HW Kaufman Group, framed the shift as a call to participate rather than watch from the sidelines. “Leaders being really present with their teams, co-creating with their teams, being transparent, and really being part of the process, as opposed to letting things happen, will make a really big difference,” she said, adding that the day’s biggest takeaway was simple: “Raising your hand to take on something that might be uncomfortable.”
Mentorship, sponsorship, and paying it forward
Alongside the AI conversation ran an equally strong current: the responsibility senior women feel to open doors for the next generation. Justina Morris, Senior Vice President at Alliant Insurance Services’ Healthcare Practice, pointed to a gap many in the room recognized in themselves. “A lot of the women in the room raised their hand that they didn’t have mentors, they didn’t have sponsors,” she said. “That was one of the key things that everybody should walk away from here.”
Karen Williams, Senior Managing Director in the Private Equity Vertical at Brown & Brown, brought decades of perspective to that same point, urging younger professionals to build the skills that will outlast automation. “The skill sets that need to be developed for the future” include communication, “actively seeking discomfort,” and making decisions when information is incomplete, she said, adding that sponsorship conversations happening “behind closed doors” remain one of the most powerful tools for advancing women in the industry.
Karen Latona, Vice President of the Midwest Region at AmTrust Insurance, closed her session by dismantling advice she was given early in her career, that empathy was a weakness. “I feel empathy is a superpower, especially as a leader,” she said. Looking ahead, she named talent as the industry’s most urgent challenge, with retirements accelerating faster than new talent is coming in, and called on the room to help the next generation see insurance as the wide-open career path it is: “You’re not limited.”
Celebrating the women shaping the industry
The day closed with a dedicated presentation honoring a group of elite women in insurance, recognizing the outsized impact they’ve had on their companies and the broader industry, from building new practices to reshaping how their organizations train and retain talent.
See you in 2027
Women in Insurance Live has quickly become one of the industry’s must-attend gatherings, and this year’s Chicago edition proved why. The conversations, the connections made on the river cruise, and the honest reckoning with where insurance is headed all point to one thing: this community is only getting stronger. Women in Insurance Live will be back next year, and this is one conversation you won’t want to miss.
