Mentorship, ambition, flexibility and artificial intelligence dominated the conversation as insurance leaders gathered in Toronto for Insurance Business Canada's Women in Insurance Summit Canada.
The numbers set the context: women make up roughly two-thirds of Canada's insurance workforce but hold only 18% of SVP roles, and the share feeding into executive positions has declined by 10% over the past three years. The talent is there – the systems around it are not converting.
For Rola Dagher (pictured), former president and CEO of Cisco Canada and former global channel chief at Dell Technologies, that gap is personal. Dagher arrived in Canada in 1989 as a teenage mother fleeing wartime Lebanon, with no English and no formal degree. She built her career from a telemarketing role at Bell Canada through increasingly senior positions at Dell and Cisco, guided by a three-part framework: learn it, earn it, return it.
"Pressure does not break you, it reveals who you are," Dagher said. "Comfort and growth do not coexist. Period. Full stop."
She urged leaders to praise effort and creativity over intelligence, arguing that telling someone "you're so smart" reinforces a fixed mindset, while recognizing original thinking compounds over time. And she was direct about the obligation that comes with seniority: "There is a beautiful spot in heaven for every woman that actually helps another woman."
That idea – what ambition actually looks like, and who gets to claim it – surfaced repeatedly. Sharla Postic, chief administrative officer at Securian Canada, recalled a time when ambition in a man signalled drive and strategic thinking, while the same quality in a woman was more often labelled as aggressive.
"I'm feeling very encouraged that those perspectives are changing," Postic said, adding that what accelerates readiness for senior roles comes down to exposure, sponsorship, and being trusted to lead through complexity.
Mackenzie Oldfield, team lead in private and not-for-profit financial lines at Chubb, said the shift is already visible among younger professionals, for whom ambition is less about endurance and more about purpose.
"Ambition these days is not about surviving your job," Oldfield said.
She noted that the industry is attracting early-career talent well – through university programs, insurance courses, and campus outreach – but that retention is the harder problem. Stability alone will not hold a generation that values continuous learning, and when someone signals they are ready for more, the worst response is "just keep working at it." Stretch goals, lateral moves, and outside opportunities such as board roles or industry associations do more to retain hungry talent than perks do, she said.
Flexibility came up in the same breath. Brenda Gibson, president and CEO of Red River Mutual, pushed back on the idea that it is purely a generational want, calling it something women have needed for a long time.
"You can say you have a flexible culture," Gibson said, "but are you living and breathing that every day?"
On the business side, artificial intelligence and economic pressure drew equally sharp perspectives. Geneviève Fortier, CEO of Promutuel Insurance, said AI will fundamentally reshape underwriting, pricing, claims management, and customer relationships – and that the bigger risk is not moving too fast but failing to retool business processes in time to capture the value.
In a market shaped by inflation, rising claims costs, and a softening commercial cycle, Fortier said discipline in core operations remains the surest path through.
"If you're not being good at balancing what you have to do short term without losing what you're trying to accomplish mid to long term, you're going to get out of this in a weakened position," she said.
If there was a single thread running through the day, it was this: leadership is not a title – it starts the moment you decide to make space for someone else. Whether that means mentoring a junior colleague, sponsoring a lateral move, or simply speaking to a woman's business impact when she is not in the room, elevation is a daily act, not a destination.
