Assistant Captive Director, Benefits

Gallagher•Rolling Meadows, IL

12d

About The Position

Reporting to the Captive Director, the Assistant Captive Director, Benefits is responsible for retaining, growing, and managing one or more Medical Stop Loss (MSL) Group Captives. The successful candidate will serve as a trusted advisor to captive members, clients, brokers, and service providers, helping drive the continued success and long-term growth of these complex risk financing programs. This is a highly visible role that combines client relationship management, strategic program oversight, and operational leadership. The individual will play a key role in guiding renewal strategy, supporting member engagement, analyzing program performance, and delivering exceptional service to captive participants. Working closely with internal stakeholders and external partners, this position offers the opportunity to influence business outcomes, solve complex challenges, and contribute to the growth of one of the industry's leading captive insurance organizations.

Requirements

Insurance qualification would be advantageous e.g. ARe or equivalent.
Minimum of five years 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 skills, including Excel, Word and PowerPoint.
Demonstrable ability to manage teams, multi-task and adapt to changing priorities.
Highly motivated individual who is deadline driven and committed to delivering an excellent level of client service.
Excellent verbal, written, organizational skills with the ability to engage effectively at all levels.
Demonstrable career progression in previous roles.
Assisting with strategic direction of the team
Strong working knowledge of captives, benefits, risk management

Responsibilities

Manage the captive renewal process which includes the gathering, assembling and presentation of the updated client underwriting information.
Sell the renewal to current insured and provide explanation for increases and decreases.
Manage the preparation, planning and materials for regular captive Member meetings.
Coordinate the loss summary information for distribution to the clients and the service providers.
Respond to client needs and inquiries in a timely fashion.
Work with Captive Director to follow up with prospects or referrals from our insureds/brokers.
Ensure that collateral is in place for each member and make sure that members understand the new requirements each year as needed.
Maintain various schedules as it relates to the company’s premium payments, letters of credit, loss experience charges and claim payments.
Manage the policy issuance and premium audit processes.
Coordinate the policy errors and omissions review.
Manage the premium invoicing process and monitor cash receivables.
Review new business and renewal loss pick projections from carrier partners.
Review loss summaries on new business and perform initial analysis for the Captive Director.
Maintain the captive’s template of coverage for medical stop loss.
Maintain a positive and professional relationship with captive service providers, clients and their consultants.
Anticipate client and program needs and problem and proactively offer solutions.
Manage systems and account service to comply with corporate professional standards.
Direct and monitor the performance of the captive team’s service consultants.
Work on special projects as required.