Diane Brassard
Head of Education and Advocacy
With over 30 years of experience spanning claims, underwriting, automation, and operational leadership, Diane Brassard serves as Head of Education and Advocacy at Roots. In this role, Diane bridges decades of insurance expertise with cutting-edge AI solutions—helping organizations understand, embrace, and implement intelligent automation to transform how insurance gets done.
Before joining Roots, Diane served as BPO Engagement Owner at WR Berkley – Regional Shared Services, where she was responsible for managing the strategic relationship between business stakeholders and BPO partners. In this role, she oversaw the successful execution of offshore initiatives, ensured service alignment with underwriting and claims teams, and drove process improvements to enhance operational performance and scalability.
Prior to that, she served as AVP and Director of Underwriting Operations at Berkley Mid-Atlantic Insurance Group and held senior underwriting operations roles at Colony Specialty (Argo Group), including leadership over Marine business functions.
Earlier in her career, Diane spent more than two decades at The Main Street America Group, progressing through roles in claims, training, automation, and technology deployment. Throughout her tenure, she focused on improving experiences for both internal teams and agent-facing customers—delivering training, process enhancements, and automation solutions that increased service quality and supported operational growth across the organization.
Today, Diane leads the development of Roots thought leadership and educational strategy—creating webinars, workshops, and white papers that empower insurers to confidently adopt AI-powered solutions. Her comprehensive industry perspective and passion for operational transformation make her a powerful advocate for the future of intelligent insurance.
