Program Manager - Group Captives

Ryan Specialty, LLC; Chicago (IL); On-site; USD 116,000 - 145,000; Full time

Benefits offered by this job

Bonuses

Benefits package

Job summary

Ryan Specialty, LLC in Chicago is seeking a proactive Program Manager to oversee the daily operations of group captive insurance programs, coordinating brokers, members, and service providers to ensure smooth execution. You will lead cross-functional teams, manage underwriting data flow from submission to pricing, and help prepare proposals and board materials with accuracy and timeliness.

The role emphasizes strong communication, analytical thinking, and a collaborative culture, with

Qualifications

• Bachelor’s degree in a related field with at least five years in property and casualty insurance, ideally captive programs.
• Strong collaboration across executive leadership, production and underwriting teams.
• Ability to organize, prioritize and communicate complex information clearly.

Responsibilities

• Program Management & Leadership: lead day-to-day operations of captive programs and align with executives.
• Production: oversee underwriting data flow, review submissions, and support pricing models.
• Client & Partner Relationships: maintain brokers, service providers, and member relationships; lead board updates.
• Program Documentation & Financial Oversight: ensure up-to-date board books, financials, renewals, and slide decks.
• Premium Collection & Financial Reconciliation: monitor premium collection and ensure accurate reconciliation.

Skills

Cross-functional collaboration

Strong organizational skills

Excellent written and verbal comms

Analytical thinking

Education

Bachelor’s degree (or equivalent) in a related field

Tools

Microsoft Excel

PowerPoint

Adobe Acrobat

Job description

Position Summary

We are seeking a proactive and detail-oriented Program Manager to oversee the daily operations of assigned group captive insurance programs. In this role, you will manage technical aspects related to brokers, members, and service providers, ensuring smooth and efficient program execution. The Program Manager will work closely with internal teams and external service providers to drive success and contribute to the growth and effectiveness of our group captive programs.

Key Responsibilities

• Program Management & Leadership: Act as your assigned captive(s) Chief Operating Officer by leading the day to day operations, providing support to the team handling many of the technical aspects of the captive. Foster a collaborative environment by working closely with the Captive Executive(s), Business Development Executives and other Program Managers to align on all captive business activities.
• Production: Oversee the flow of underwriting information from submission to proposal production. Review submissions and underwriting data, ensuring accuracy and completeness before sending to actuaries to generate pricing models. Collaborate with the underwriting team to create proposals, ensuring timely and accurate production for the Captive Executive.
• Client & Partner Relationships: Maintain strong relationships with brokers, service providers, and members, ensuring timely and accurate execution of all program activities. Take a lead role in facilitating board meetings, ensuring clear communication of program status and updates.
• Program Documentation & Financial Oversight: Oversee the preparation and submission of underwriting documentation for renewals and board books. Work closely with captive domicile manager to ensure all program documentation is up-to-date and accurate including board books, financials, renewal books, and slide decks.
• Premium Collection & Financial Reconciliation: Monitor the collection of premium and ensure accurate financial reconciliation in collaboration with the captive domicile manager and policy issuing carrier, maintaining financial integrity and compliance.

Travel Expectations

• Minimal to no travel required, aside from attending the annual board meetings, which are typically held at offshore locations.

Key Priorities

• Accuracy and attention to detail in all program deliverables.
• Timeliness in meeting deadlines and managing multiple priorities.
• Building and maintaining strong relationships with brokers, service providers, and clients.
• Fostering a positive, collaborative team culture.

Required Qualifications

Education & Experience

• Bachelor’s degree (or equivalent) in a related field, with a minimum of five (5) years of experience in property and casualty insurance, ideally with exposure to captive programs.

Skills & Competencies

• Proven ability to collaborate effectively with cross-functional teams, including executive leadership and production.
• Strong organizational skills, with the ability to prioritize and manage multiple tasks in a fast-paced environment.
• Excellent written and verbal communication skills, with the ability to present complex information clearly.
• Strong analytical skills, with the ability to solve problems and apply sound judgment to technical and operational challenges.
• High level of proficiency with Microsoft Office applications (especially Excel and PowerPoint) and Adobe Acrobat.
• A positive, proactive attitude with a commitment to customer service and business culture.

Why Join Us

This is an exciting opportunity to play a pivotal role in managing complex captive insurance programs while contributing to a dynamic and growing team. We value individuals who are proactive, communicative, and committed to continuous improvement, both personally and professionally.

This opportunity offers an annual performance-based based target

Ryan Specialty is an Equal Opportunity Employer. We are committed to building and sustaining a diverse workforce throughout the organization. Our vision is an inclusive and equitable workplace where all employees are valued for and evaluated on their performance and contributions. Differences in race, creed, color, religious beliefs, physical or mental capabilities, gender identity or expression, sexual orientation and many other characteristics bring together varied perspectives and add value to the service we provide our clients, trading partners, and communities. This policy extends to all aspects of our employment practices, including but not limited to, recruiting, hiring, discipline, firing, promoting, transferring, compensation, benefits, training, leaves of absence, and other terms, conditions, and benefits of employment.

How We Support Our Teammates

Benefits Curious about Ryan Specialty’s benefits? Explore our employee benefits here! Ryan Specialty seeks to offer our employees a comprehensive and best-in-class benefits package that helps them — and their family members — achieve their physical, financial, and emotional well-being goals. In addition to paid time off for company holidays, vacation, sick and personal days, Ryan offers paid parental leave, mental health services and more. The target salary range for this position is $116,000.00 - $145,000.00 annually. The wage range for this role considers many factors, such as training, transferable skills, work experience, licensure and certification, business needs, and market demands. The pay range is subject to change and may be modified in the future. Full-time roles are eligible for bonuses and benefits. For additional information on Ryan Specialty Total Rewards, visit our website https://benefits.ryansg.com/.

We provide individuals with disabilities reasonable accommodations to participate in the job application or interview process, to perform essential job functions, and to receive other benefits and privileges of employment in accordance with applicable law. Please contact us to request an accommodation at [e-mail] The above is intended to describe this job's general requirements. It is not to be construed as an exhaustive statement of duties, responsibilities, or physical requirements. Nothing in this job description restricts management's right to assign or reassign duties and responsibilities to this job at any time. Reasonable accommodations may be made to enable individuals with disabilities to perform essential functions.

A multi-time winner of Newsweek’s Most Loved Workplaces and Insurance Business’s Top Insurance Employers, Ryan Specialty is home to some of the brightest talent in the insurance industry. Join our team and help provide innovative solutions for insurance brokers, agents and carriers.