Cailyn Healy

Cailyn Healy is an accomplished insurance professional with over fifteen years of experience in Property & Casualty and Life Insurance. She currently serves as the Agency Manager at Comparion Insurance Agency, where she provides strategic leadership, mentorship, and guidance to a team of licensed agents. Throughout her career, Cailyn has focused on driving performance, setting clear goals, and creating tailored business plans to ensure her team’s success while aligning with organizational growth objectives. She is known for fostering a collaborative environment that encourages continuous improvement and professional development.

Cailyn began her career in insurance administration shortly after completing her education, gradually advancing into management roles at Liberty Mutual and Comparion Insurance. She is particularly proud of her transition from administrative roles to full-time recruiting and leadership, finding fulfillment in the tangible impact she makes in her community and in the careers of those she mentors. Her dedication and strategic approach have earned her recognition within the industry, including multiple managerial awards during her tenure at Liberty Mutual.

Beyond her professional achievements, Cailyn is committed to giving back to her community. She actively supports initiatives such as Adopt a Family and the Food Banks of Western Massachusetts, reflecting her belief in service and community engagement. With a Master’s degree in Corporate Communications and Leadership from Northeastern University and additional certifications from The American College of Financial Services, Cailyn combines technical expertise with a motivational leadership style, empowering both her team and clients to achieve their goals.

• LUTCF

• Northeastern University- Master's
• The American College of Financial Services
• Knox College- Bachelor's

• Summer Sales Organization
• Crown Awards for Production