The story of what Rose Freeman built in rural Saskatchewan and
why it’s changing how people experience insurance.
There’s a version of Rose Freeman’s story that sounds like the beginning of a big-city career. Corporate finance. A rising trajectory. A promotion on the table and a skyline waiting.
Not because she was afraid of what was ahead, but because she already knew what success looked like for her. It looked like Saskatchewan. It looked like small towns where people know your name, where a handshake still means something, and where showing up matters more than showing off.
In 2013, Rose did something that surprised many. She purchased a small insurance brokerage in Shell Lake with a background in finance, almost no brokerage experience, and a short window to complete her licensing.
“No opportunity there,” they said.
She heard something entirely different.
She completed her licensing. She wrote the business plan. She took on her first clients. And she welcomed her first daughter, all within months of each other.
What followed was proof that opportunity isn’t granted by a skyline or a postal code. It’s something you create by bringing your own perspective to a place and people that need it.
A few years after opening in Shell Lake, Rose expanded Willow Insurance to a second location in Debden, Saskatchewan, while expecting her second child.
Willow Insurance doubled its premium-written book of business in just four years, a growth that typically takes ten years in the industry.
Rose credits relationships. She credits her team. And she credits a stubborn conviction that if you serve people well, truly well, the rest takes care of itself.
Today, the Willow Insurance family continues to serve communities across north-central Saskatchewan with offices in Shell Lake and Debden, and operates as a remote broker across all of Saskatchewan. The brokerage Rose built from a single location, while expecting her first child, has become one of the most decorated independent brokerages in the province.
“Willow Insurance looks beyond a quick fix to find the right fit.”
That’s not a tagline. It’s how Rose has run this business since day one and the world is taking notice.
Rose doesn’t separate her business from her community. She never has. For her, showing up for the people
around you isn’t a strategy; it’s simply what you do.
In 2023, Rose was selected as an ambassador for the Make-A-Wish Foundation’s inaugural Women For Wishes campaign, one of 100 inspiring women across Canada and one of just 20 from Saskatchewan chosen for this honor. To date, she has raised more than $31,000 for the campaign — every dollar of which stays in Saskatchewan to fulfill children’s wishes across the province.
Right at home, through Willow Insurance, Rose has contributed to the construction of an additional ball diamond in Shell Lake, a new spray park in Canwood, and the continued operation of the Debden curling and skating facility because Rose knows that strong communities don’t happen by accident. They happen because people choose to invest in them.
— Rose Freeman, Founder & CEO
In the last decade alone, Rose Freeman has earned eight national industry recognitions. It is a record that places her among the most decorated insurance brokers in Canada. The awards are notable, but what they represent is more impressive.
They are the industry’s way of saying that what Rose built in Shell Lake, with a finance background, no brokerage experience, and a new baby, matters because it is the product of a true trailblazer.
Insurance Broker of the Year — Regional (Prairies & Maritimes)
Insurance Business Canada 2025
Elite Woman in Insurance
Insurance Business Canada 2022, 2025
Top Insurance Brokers — Canada
Insurance Business Canada 2024, 2025
Cansure Award — Insurance Broker of the Year Finalist
Insurance Business Canada 2022, 2023, 2024
Global Best In Insurance Special Report
Global Best In Insurance International
Rose serves on committees through the Insurance Brokers’ Association of Saskatchewan, helping guide conversations that shape the future of provincial
insurance. She has been invited to speak at national conferences, sharing her perspective as a rural broker, female entrepreneur, and advocate for people-first leadership.
In 2023, she was honoured to speak at the SGI CANADA national convention as the Saskatchewan Delegate, sharing her story of resilience and her belief that kindness is not a soft skill. It is a leadership strategy.
She has also appeared on provincial and national panels, championing women in insurance and rural entrepreneurship across Canada.
Rose’s story has been featured by local and national media. Read the full stories below.
Insurance Business Canada (2026)
Prince Albert Daily Herald (2026)
Insurance Business Canada (2025)
Insurance Business Canada (2022)
Insurance Business Canada (2022)
Rose Freeman is a Saskatchewan mom raising daughters. She teaches them by example, not with words about what matters but by living it in front of them every day.
She believes deeply that resilience isn’t something you find after you’ve made it. It’s something you build through how you show up for your clients, your team, your
community, and the people at home who are watching everything you do.
Her daughters are watching, and what they see is a woman who chose home when the world told her to go bigger. They see a woman who made something extraordinary out of exactly where she was.
“Rose is a living example of resilience — that no matter what challenges life presents, anyone can bounce back and find happiness when they nurture and give kindness to themselves, their families and their communities.” — Michele Charles Gustafson, Business Consultant
She champions women in insurance. She speaks about leadership on national stages, and then she comes home to Shell Lake, because that was always the point.
Willow Insurance is powered by a team of dedicated professionals who share Rose’s
commitment to education, preparation, and genuinely personalized service. Every member
of this team is part of what makes the WillowGuide Experience what it is.
Founder & CEO
Assistant Branch Manager
Commercial Broker – Remote
Personal Lines Broker
Rose and her team are welcoming clients seeking more than a transactional insurance experience. If you value preparation, clear communication, and a relationship that lasts we’d genuinely love to meet you.
Whether you’re protecting a family home, managing farm operations, running a business, or building your Saskatchewan dream, we’re here to guide you through it with clarity, expertise, and care.
— The Willow Insurance Team
