Whitney Benson, 39 – CaptiveSimple – Founder COO/CTO
Whitney is a seasoned insurance professional, entrepreneur, and community advocate with nearly 20 years of industry experience. As COO and Marketing Manager at Paramount Insurance, and co-founder of CaptiveSimple.
Under her leadership, Paramount was named Best Small Brokerage of the Year (2025) by the Insurance Brokers Association of Alberta, and CaptiveSimple was recognized as a finalist for a U.S. Technology Solution Award.
Whitney’s commitment to community matches her entrepreneurial spirit. She launched Paramount’s #30years30charities campaign, supporting organizations like Big Brothers Big Sisters, the Central Alberta Pregnancy Centre, and the Christmas Bureau.
She also spearheaded Central Alberta Brokers’ Day with Canadian Blood Services, filling 70 donor spots, and actively supports causes including Dress for Success Central Alberta, Red Deer Hospice, and the Terry Fox Foundation.
Her dedication to education is evident in her mentorship of Career Assistance Network’s Financial Fast Track students and her work educating Alberta brokers about captives, an innovative model that, if scaled, could redirect significant capital back into local economies.
Whitney’s leadership is grounded in authenticity, compassion, and resilience. She believes in leading by example, showing her children and her community that kindness, hard work, and grace are powerful forms of strength.
Her proudest accomplishments include not only industry accolades, but the personal journey of growing as a woman, mother, and leader learning to embrace imperfection and lead with heart.
She finds inspiration in the lightbulb moments of those she mentors especially women when they realize they are worthy of success, growth, and opportunity. Whitney’s work is a testament to the belief that when we serve others as we climb, we build stronger businesses, communities, and futures.
“Quiet leadership can make a powerful impact”