Rose Freeman, Owner of Willow Insurance Corp.
From supporting local youth recreation projects to shaping the future of Saskatchewan’s insurance industry, Rose Freeman believes success is built through giving back. As the Founder and CEO of Willow Insurance Corp., Freeman’s approach to leadership reflects the spirit of International Women’s Day’s 2026 theme, “Give to Gain.”
Freeman founded Willow Insurance 13 years ago and has grown the brokerage into a trusted regional business serving communities across north-central Saskatchewan. With offices in Shell Lake and Debden and a remote broker based in Melfort, Willow Insurance has built its reputation on strong relationships and community commitment.
Her leadership has earned eight national recognitions, including Insurance Broker of the Year (Regional – Prairies & Maritimes), Elite Woman, and Top Broker honors from Insurance Business Canada in 2025.
At the core of Freeman’s business philosophy is an education-based approach to insurance. Her brokerage prioritizes helping clients understand their coverage and available options so they can make informed decisions to protect their families, farms, and businesses.
“Insurance has become incredibly complex. We simplify insurance.” Freeman says. “When clients understand their coverage, they feel empowered to make the best decisions for their future.”
Beyond her brokerage, Freeman contributes to shaping the industry itself. She serves on several committees through the Insurance Brokers’ Association of Saskatchewan, helping guide discussions that influence the future of the provincial insurance sector. She has also been invited to speak at several national conferences, sharing insights as both a rural broker and female entrepreneur.
Community support remains central to Willow Insurance’s mission. The company has contributed financially to projects including the construction of an additional ball diamond in Shell Lake, the development of a new spray park in Canwood, and the continued operation of the Debden curling and skating rinks initiatives that help create opportunities for local youth to stay active and engaged in their communities.
Freeman also serves as a Women for Wishes Ambassador for Make-A-Wish Saskatchewan, helping raise more than $30,000 over the past three years to support life changing wishes for children with critical illnesses.
Within her own workplace, Freeman also prioritizes employee wellbeing. Willow Insurance introduced a Work-Life Support Benefit program designed to support employees with domestic services that help reduce the mental load outside of work and improve overall work-life balance.
“Supporting people whether that’s clients, employees, or community members is at the heart of what we do,” Freeman says. “When we invest in others, we build stronger businesses and stronger communities.”
Freeman believes this philosophy reflects the true meaning of “Give to Gain.” By investing in community, mentoring others, and leading with compassion, she continues to demonstrate how giving back creates lasting impact far beyond business success.
