When Rose Freeman (pictured) was offered the classic corporate dream – a promotion in finance and a move to a big‑city tower – she realised, almost to her own surprise, that it wasn’t her dream at all. Instead, she went home.
Back in rural Saskatchewan, where people warned her there was “no opportunity,” Freeman built Willow Insurance Corporation around a very different idea of success: that opportunity isn’t something granted by a skyline or a postal code, but something you create by bringing your own perspective to an industry that needs it.
That rethinking of what a career (and a company) can look like is exactly what Freeman will bring to the stage as a panellist at this year’s Women in Insurance Summit. As Founder and CEO of Willow, she has quietly turned her values into operating decisions that challenge some of the industry’s deepest assumptions about work, flexibility and who gets to lead.
Ask Freeman what meaningful progress for women in insurance will look like over the next decade, and she doesn’t hesitate: far better representation in leadership, backed by systems that don’t quietly penalise people (often women) for their lives outside the office.
“Insurance is full of women in frontline and junior roles,” she notes, “but as you go up the ladder, those roles are still disproportionately held by men. That’s not representative of who actually keeps this industry running.”
Some of the barriers are obvious: travel‑heavy roles, rigid hours, expectations that key meetings happen when caregivers are needed at home. Others are more subtle: the mental load of planning dinners, coordinating childcare, managing a household on top of demanding jobs. Rather than simply acknowledging these realities, Freeman has started redesigning work at Willow to account for them.
This year, the company introduced a work‑life balance spending account, funded entirely by the employer. Staff can use it for prepared meal services, cleaning, laundry, or professional organisers – any support that helps reduce the domestic mental load so they can show up fully at work and at home.
“If you’re spending your entire weekend doing laundry, cleaning and cooking, you’re not actually getting a break. Lifting some of that load helps level the playing field.”
Willow also offers 100% remote roles, a decision driven partly by the realities of recruiting in a rural labour market, but just as much by a belief that traditional work structures no longer fit how people live.
“Our rigid nine‑to‑five, Monday‑to‑Friday model is old and obsolete,” Freeman says. “It simply doesn’t work for everyone anymore. If we want more women at the table, we have to look hard at those structures and be willing to change them.”
Freeman likes to quote Bill Bernbach, an American advertising creative director: “It’s not a principle until it costs you money.” It’s a standard she applies rigorously to her own business.
“Every organisation has a list of values,” she says. “But if you only hold them when it’s convenient, they’re not really principles.”
At Willow, those principles have very real price tags. The work‑life balance account is fully employer‑paid. The company has closed its doors on Mondays in July and August to give the team time to regroup in the face of regulatory and market changes. And advisors routinely spend more time with clients than a pure volume model would recommend.
She describes it with a story about two people chopping wood: one works straight through, the other disappears at lunch and still chops more wood every day. When asked where he goes, he answers: “I go home and sharpen my axe.”
“Closing on Mondays absolutely cost us money in the short term,” Freeman says. “But it sharpened our axe. The team was more confident, better prepared and less burnt out. Long term, that’s what supports quality of work – and that’s what supports careers.”
The same philosophy underpins Willow’s education‑first approach to clients. The firm has moved away from quick walk‑in transactions toward booked, hour‑long conversations that explore clients’ risks, priorities and budgets in detail.
“The perfect insurance policy is the one that lets you sleep at night and fits your budget,” she says. “That looks different for everyone. You can’t get there in 15 minutes purely by chasing the lowest premium.”
Freeman is open about how closely her business life and family life have intertwined. As a self‑employed owner, she had three children without access to traditional maternity leave. The office became part workplace, part nursery, and, over time, a classroom.
Her kids grew up around the brokerage, first in bouncers and small desks in the corner, later learning to print reports, count money and make simple phone calls. They write and sign the giant presentation cheques Willow donates to local projects – a ball diamond, a spray park, a skating and curling facility – and present them at community meetings.
“They understand that our business is part of how the community runs, and that volunteers and local organisations make all of these things possible,” Freeman says. “Those are lessons you can’t teach only in theory.”
She also sees a direct link between the “million tabs open” mental load that many women carry and the kind of critical thinking good insurance work demands. Planning kids’ activities, meals, carpools and schedules five steps ahead, she argues, translates surprisingly well into anticipating clients’ unspoken risks.
“A client might say they just need house insurance,” she explains. “Then in passing they mention they’re going to the cabin on the weekend and riding quads. That’s when you stop and say, ‘Hold on, none of that was on your list. Let’s make sure it’s properly covered.’ You have to be able to read between the lines.”
For Freeman, that ability to see around corners (something many women develop out of sheer necessity) is not a weakness or distraction. It is a leadership asset the industry should value far more.
Join the Women in Insurance Summit Canada 2026 on June 2 at Universal Eventspace in Vaughan, ON, to turn representation into leadership. Hear from industry leaders, build your network, and leave with practical strategies to advance women into decision‑making roles.
