Assistant Captive Director, Benefits

Arthur J. Gallagher · Rolling Meadows

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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.

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, 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.

• Manage the captive renewal process, including the collection, compilation, analysis, and presentation of updated client underwriting information.
• Lead renewal discussions with insured members, clearly communicating rate changes, coverage modifications, and factors impacting premium increases or decreases.
• Coordinate the planning, preparation, and delivery of materials for recurring captive member meetings.
• Oversee the collection and distribution of loss summary reports to clients and captive service providers.
• Provide responsive, high-quality service by addressing client inquiries and resolving issues in a timely manner.
• Partner with the Captive Director to cultivate new business opportunities and follow up on prospect and referral activity from insureds and brokers.
• Ensure all collateral requirements are met and educate members on annual collateral obligations and changes.
• Maintain and monitor schedules related to premium payments, letters of credit, loss experience charges, and claims payments.
• Manage policy issuance, endorsement activity, and premium audit processes to ensure accuracy and compliance.
• Coordinate policy reviews and errors and omissions (E&O) assessments.
• Oversee premium invoicing activities and monitor accounts receivable to support healthy cash flow management.
• Review new business and renewal loss projections provided by carrier partners and identify key trends and exposures.
• Analyze loss summaries for prospective business and provide initial recommendations and insights to the Captive Director.
• Maintain and update medical stop-loss coverage templates to ensure consistency and accuracy across the captive program.
• Foster strong, professional relationships with captive service providers, clients, brokers, and consultants.
• Anticipate client and program needs, proactively identifying challenges and implementing effective solutions.
• Ensure account management activities and systems adhere to corporate policies, procedures, and professional standards.
• Provide leadership, direction, and performance oversight for the captive service consulting team.
• Support strategic initiatives and special projects that contribute to the growth and success of the captive program.
• Captive program management
• Client relationship management
• Renewal strategy and underwriting coordination
• Alternative risk and captive insurance expertise
• Financial and collateral management
• Loss analysis and reporting
• Team leadership and operational oversight
• Business development support and prospect engagement
• Process improvement and problem solving

• 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

At Gallagher, we believe supporting our colleagues goes far beyond the role itself. For more information, visit our Benefits page.

• 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 

At Gallagher, we are dedicated to building an inclusive and authentic workplace. If your past experience doesn’t align perfectly, we encourage you to join our Talent Community to stay connected to additional career opportunities. At times, we will consider transferable skills from previous roles.

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

• Manage the captive renewal process, including the collection, compilation, analysis, and presentation of updated client underwriting information.
• Lead renewal discussions with insured members, clearly communicating rate changes, coverage modifications, and factors impacting premium increases or decreases.
• Coordinate the planning, preparation, and delivery of materials for recurring captive member meetings.
• Oversee the collection and distribution of loss summary reports to clients and captive service providers.
• Provide responsive, high-quality service by addressing client inquiries and resolving issues in a timely manner.
• Partner with the Captive Director to cultivate new business opportunities and follow up on prospect and referral activity from insureds and brokers.
• Ensure all collateral requirements are met and educate members on annual collateral obligations and changes.
• Maintain and monitor schedules related to premium payments, letters of credit, loss experience charges, and claims payments.
• Manage policy issuance, endorsement activity, and premium audit processes to ensure accuracy and compliance.
• Coordinate policy reviews and errors and omissions (E&O) assessments.
• Oversee premium invoicing activities and monitor accounts receivable to support healthy cash flow management.
• Review new business and renewal loss projections provided by carrier partners and identify key trends and exposures.
• Analyze loss summaries for prospective business and provide initial recommendations and insights to the Captive Director.
• Maintain and update medical stop-loss coverage templates to ensure consistency and accuracy across the captive program.
• Foster strong, professional relationships with captive service providers, clients, brokers, and consultants.
• Anticipate client and program needs, proactively identifying challenges and implementing effective solutions.
• Ensure account management activities and systems adhere to corporate policies, procedures, and professional standards.
• Provide leadership, direction, and performance oversight for the captive service consulting team.
• Support strategic initiatives and special projects that contribute to the growth and success of the captive program.
• Captive program management
• Client relationship management
• Renewal strategy and underwriting coordination
• Alternative risk and captive insurance expertise
• Financial and collateral management
• Loss analysis and reporting
• Team leadership and operational oversight
• Business development support and prospect engagement
• Process improvement and problem solving

• 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

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