Assistant Captive Director, Benefits

Arthur J. Gallagher & Co. (AJG); Rolling Meadows (IL); On-site; USD 120,000 - 160,000; Full time

Job summary

Artex is seeking an Assistant Captive Director, Benefits to retain, grow, and manage Medical Stop Loss Group Captives. You will guide renewal strategy, engage members, analyze performance, and deliver excellent service to captive participants.

This is a highly visible role requiring collaboration with brokers, clients, and service providers. You will lead renewal planning, oversee member meetings, and coordinate cross-functional efforts to ensure accurate underwriting, cash flow, and compliance

Qualifications

• Experience leading teams in re/insurance or risk management.
• Strong client service orientation and relationship building.
• Proven ability to manage multiple priorities and meet deadlines.
• Knowledge of captives, benefits, and risk management concepts.

Responsibilities

• Manage captive renewal processes and present updated underwriting information.
• Coordinate and communicate renewal terms to insureds and brokers.
• Lead regular captive member meetings and prepare supporting materials.
• Oversee loss summaries and provide analysis for Captive Director.
• Ensure compliance with professional standards in service delivery.
• Direct and monitor the captive team’s consultants and projects.

Skills

Team management

Client service

Communication

Risk management

Deadline driven

Tools

Excel

Word

PowerPoint

Job description

Introduction

At Artex, we reimagine what risk management can be and we do it with bold thinking, deep expertise, and an unwavering belief in what’s possible. As part of our global team, you’ll help clients navigate complex risks through creative, forward-looking solutions that go beyond the expected. This is a place where innovation is encouraged, ideas are welcomed, and no two days look the same. We’re a community of confidently curious problem-solvers, opportunity seizers, and collaborative thinkers, working together to challenge convention and shape the future of our industry. Here, you’ll be supported to explore your potential, grow your expertise, and make a meaningful impact on a global scale.

Overview

Assistant Captive Director, Benefits

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, analysing 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 organisations.

How you’ll make an impact

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.

About You

Qualifications and skills required:

• 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, organisational 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

Compensation and benefits

• Competitive compensation
• Comprehensive benefits programs designed to support your well-being
• Career development opportunities and ongoing learning
• A collaborative, people-first culture with accessible leadership
• The opportunity to do meaningful work with global reach and local impact

Gallagher is an affirmative action/equal opportunity employer (Minorities/Females/Veterans/Disabled)