Assistant Captive Director, Benefits

Artex Risk Solutions; Rolling Meadows (IL); On-site; USD 100,000 - 140,000; Full time

Benefits offered by this job

Competitive compensation

Comprehensive benefits program

Career development opportunities

Collaborative, people-first culture

Job summary

Artex is seeking an Assistant Captive Director, Benefits to lead and grow one or more Medical Stop Loss Group Captives. You will guide renewal strategy, engage members and brokers, analyze performance, and deliver exceptional service.

This highly visible role requires strategic thinking, relationship management, and strong leadership to drive long-term growth. This position reports to the Captive Director and offers opportunities to influence outcomes, collaborate with stakeholders, and advance

Qualifications

• 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 including Excel, Word and PowerPoint.
• Demonstrable ability to manage teams, multi-task and adapt to changing priorities.
• Highly motivated, deadline-driven, and committed to client service.
• Excellent verbal, written, organizational skills 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 including gathering and presenting updated underwriting information.
• Sell the renewal to current insured and explain changes.
• Lead regular captive Member meetings and prepare materials.
• Coordinate loss summary information for clients and service providers.
• Respond to client needs and inquiries promptly.
• Support Captive Director in follow-ups with prospects or referrals.
• Ensure collateral and new requirements are understood by members.
• Maintain schedules for premium payments, LOCs, loss charges, and claims.
• Oversee policy issuance and premium audits.
• Coordinate policy errors and omissions reviews.
• Oversee premium invoicing and cash receipts.
• Review loss projections and summaries for new business and renewals.
• Maintain the captive’s coverage template for medical stop loss.
• Foster positive relationships with service providers and clients.
• Anticipate client and program needs and propose solutions.
• Manage systems and account services to corporate standards.
• Direct and monitor the captive team’s service consultants.
• Contribute to special projects as required.

Skills

Insurance knowledge

Team leadership

Excel

PowerPoint

Communication

Education

Relevant professional qualification (e.g., ARe)

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.

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

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, 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

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)