About Us

Jill O'Sullivan

Jill serves in a dual role as Director of Operations and the head of our Insurance/Medicare brokerage and advisory team. She brings more than 30 years of diverse leadership experience to the firm. She is directly responsible for strategic operations for the O’Sullivan Group client service suite, while leading the organization in the areas of strategy, communications, business development and positioning. In addition to organizational development, she provides leadership in the areas of client relationships, consultative engagements and professional standards and integrity. With a passion for team building and education, Jill also directs staff mentoring and training programs while fueling the company’s unique corporate culture, allowing TOG to attract and develop highly talented and motivated team members.

As a licensed, independent, insurance broker, Jill assists providers in developing, managing and executing their Medicare enrollment strategy to ensure maximum patient retention with a focus on maximizing provider reimbursement. In addition, Jill assists  clients in assessing their employee benefit cost structure and reviewing company funding strategies.

Jill’s many years of expertise has positioned her to be called on regularly to speak as an expert on Employee Benefit and Medicare Enrollment strategies.

Jill holds a BS Degree in Actuarial Science from the University of Illinois and has completed a rigorous course of Actuarial exams. She has completed coursework with Pepperdine University towards a Master’s Degree in Business Administration (MBA). Jill is a licensed Insurance Broker in multiple states and a member of the Insurance Ethics Association.