Assistant Captive Director, Benefits

Gallagher•Rolling Meadows, IL

83d

About The Position

The Assistant Captive Director, Benefits is responsible for retaining, growing, and managing one or more Medical Stop Loss (MSL) Group Captives. Reporting to the Captive Director, this highly visible role combines client relationship management, strategic program oversight, and operational leadership. The position serves as a trusted advisor to captive members, clients, brokers, and service providers, and supports the success and long-term growth of complex risk-financing programs. The role guides renewal strategy, supports member engagement, analyzes program performance, and delivers service to captive participants. It partners with clients, brokers, consultants, carrier partners, industry professionals, internal stakeholders, and external partners to help members understand program performance, identify trends, make informed decisions, and navigate complex challenges. The position also supports new business growth and the continued evolution of the captive platform, with exposure to Medical Stop Loss, employee benefits, captive insurance, alternative risk financing, underwriting, financial performance, and client strategy.

Requirements

Minimum of five years of post-qualifying experience within the re/insurance industry.
Minimum of five years of demonstrable team management experience.
Significant knowledge of the insurance marketplace and/or risk management regimes.
Advanced computer literacy, including Excel, Word, and PowerPoint.
Demonstrable ability to manage teams, multitask, and adapt to changing priorities.
Highly motivated and deadline driven, with a commitment to excellent client service.
Excellent verbal, written, and organizational skills, with the ability to engage effectively at all levels.
Demonstrable career progression in previous roles.
Strong working knowledge of captives, benefits, and risk management.

Nice To Haves

Insurance qualification, such as ARe or equivalent.

Responsibilities

Retain, grow, and manage one or more Medical Stop Loss Group Captives.
Serve as a trusted advisor to captive members, clients, brokers, and service providers.
Guide renewal strategy and support member engagement.
Analyze program performance and help members understand results, identify trends, and make informed decisions.
Provide operational leadership and exceptional service to captive participants.
Partner with clients, brokers, consultants, carrier partners, internal stakeholders, and external industry professionals.
Assist with the strategic direction of the team.
Support new business growth and the continued evolution of the captive platform.
Manage teams, multitask, and adapt to changing priorities.