Assistant Captive Director, Benefits
Gallagher Bassett
Rolling Meadows, IL · Posted August 18, 2026
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About the job
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, 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. How you'll make an impact Join a growing team at the forefront of Medical Stop Loss and Group Captive solutions. As an Assistant Captive Director, Benefits, you will play an influential role in the success and growth of sophisticated captive programs, partnering with clients, brokers, consultants, carrier partners, and other industry professionals to deliver innovative alternative risk solutions. Reporting to the Captive Director, this highly visible position offers the opportunity to become a trusted advisor to captive members while helping shape program strategy, strengthen client relationships, and support the long-term performance of the captive portfolio. You will be at the center of the captive experience, bringing together strategy, analytics, client engagement, and program oversight to help members navigate renewals, understand program performance, identify emerging trends, and make informed decisions. You will also collaborate across the organization and with external partners to anticipate needs, solve complex challenges, and continually enhance the value delivered to captive members. This is an exciting opportunity for someone who enjoys working in a specialized, relationship-driven environment where strategic thinking and business judgment can have a meaningful impact. The role provides broad exposure across Medical Stop Loss, employee benefits, captive insurance, alternative risk financing, underwriting, financial performance, and client strategy, along with opportunities to contribute to new business growth and the continued evolution of the captive platform. Why this opportunity stands out: Work with a highly visible, sophisticated Medical Stop Loss Group Captive programs Serve as a strategic partner to captive members, brokers, consultants, and industry partners Gain broad exposure to alternative risk, underwriting, financial performance, and captive strategy Influence client retention, program growth, and the overall member experience Collaborate with senior leaders and specialists across the business Help shape solutions for complex business and risk challenges to make a meaningful impact About You Required: Bachelor's degree and 3 years related experience OR High School Diploma/GED and 8 years related experience. Appropriate Insurance License Preferred: 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 #LI-MD6 Compensation and benefits 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)
Join a growing team at the forefront of Medical Stop Loss and Group Captive solutions. As an Assistant Captive Director, Benefits, you will play an influential role in the success and growth of sophisticated captive programs, partnering with clients, brokers, consultants, carrier partners, and other industry professionals to deliver innovative alternative risk solutions. Reporting to the Captive Director, this highly visible position offers the opportunity to become a trusted advisor to captive members while helping shape program strategy, strengthen client relationships, and support the long-term performance of the captive portfolio. You will be at the center of the captive experience, bringing together strategy, analytics, client engagement, and program oversight to help members navigate renewals, understand program performance, identify emerging trends, and make informed decisions. You will also collaborate across the organization and with external partners to anticipate needs, solve complex challenges, and continually enhance the value delivered to captive members. This is an exciting opportunity for someone who enjoys working in a specialized, relationship-driven environment where strategic thinking and business judgment can have a meaningful impact. The role provides broad exposure across Medical Stop Loss, employee benefits, captive insurance, alternative risk financing, underwriting, financial performance, and client strategy, along with opportunities to contribute to new business growth and the continued evolution of the captive platform. Why this opportunity stands out: Work with a highly visible, sophisticated Medical Stop Loss Group Captive programs Serve as a strategic partner to captive members, brokers, consultants, and industry partners Gain broad exposure to alternative risk, underwriting, financial performance, and captive strategy Influence client retention, program growth, and the overall member experience Collaborate with senior leaders and specialists across the business Help shape solutions for complex business and risk challenges to make a meaningful impact
Required: Bachelor's degree and 3 years related experience OR High School Diploma/GED and 8 years related experience. Appropriate Insurance License Preferred: 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 #LI-MD6