Assistant Captive Director, Benefits

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

• 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)