Jobs › Ryan Specialty

Wholesale Casualty Brokerage Assistant

Ryan Specialty · Chicago, IL · $25.00–$31.25 an hour · Full time

Posted Sep 21, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you managed lots of small tasks with different deadlines.

What they are checking: Whether they can keep many transactions moving without dropping any.

How do you double-check documents like quotes and binders before they go out?

What they are checking: Whether they have habits that catch errors in documents with legal and financial weight.

Why commercial insurance, and where do you see yourself growing in it?

What they are checking: Whether they want a long-term career in insurance, which the role is designed to build.

Tell me about a time you learned from a mentor and applied it quickly.

What they are checking: Whether they are coachable, which matters in a role built on hands-on training.

What would you do

A broker asks you to send a binder today, but the carrier hasn't confirmed terms. What do you do?

What they are checking: Whether they understand they cannot bind without carrier approval and communicate the delay properly.

You notice a quote has a different limit than what the broker asked for. What do you do?

What they are checking: Whether they speak up about discrepancies before they reach the client.

How do you handle a busy broker who gives you quick, unclear instructions?

What they are checking: Whether they ask smart clarifying questions without slowing the broker down.

About the work

What do you understand about how a wholesale broker works between retail agents and insurance carriers?

What they are checking: Whether they grasp the basic structure of wholesale brokerage they will support every day.

Walk me through how you'd process an endorsement request from a retail agent.

What they are checking: Whether they think through the request, carrier approval, documentation and billing in order.

What does general liability cover in a commercial policy, in your own words?

What they are checking: Whether they have a basic understanding of casualty coverage or the curiosity to learn it.

Practice this interview out loud.

Offer builds a real interview for this exact role at Ryan Specialty from your resume and this job description, asks the questions one at a time, and tells you what landed. The first one is free.

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The full job description

As published by Ryan Specialty.

RT Specialty, a division of Ryan Specialty, is a leading wholesale distributor of specialty insurance products and services. Our experienced brokers are specialized in property, casualty, professional lines, transportation and workers’ compensation, providing creative solutions to retail brokerage firms. We define ourselves through our superior execution on behalf of our clients, which has established us as a leader in the industry. Position Summary The Brokerage Assistant provides operational and administrative support to a dynamic Casualty brokerage team, helping ensure the accurate and timely processing of insurance transactions throughout the policy lifecycle. This role assists with policy administration, endorsements, quoting, binder issuance, account documentation, and account servicing activities while partnering closely with brokers, carrier partners, and internal teams. This is an excellent opportunity for a recent college graduate or early-career professional looking to build a long-term career in commercial insurance and wholesale brokerage. Through hands-on training, direct mentorship, and exposure to carrier and client relationships, the Brokerage Assistant will develop a strong foundation in brokerage operations while gaining opportunities for growth into marketing, client-facing, and brokerage-focused roles. Location: This role will work hybrid out of our Chicago office with Mon-Thurs in office and Friday's work from home. Our office is located at 540 W Madison St Floor 9 Chicago, IL 60647. What will your job entail? • Support the day-to-day servicing and administration of commercial casualty insurance accounts. • Assist brokers with quoting, quote issuance, binder preparation, policy processing, endorsements, and account documentation. • Review policies, endorsements, binders, and related insurance documents to ensure accuracy and completeness. • Prepare renewal marketing materials, submissions, cover letters, and other brokerage-related documentation. • Maintain accurate client, policy, and transaction information within agency management systems and document management platforms. • Organize and maintain account files, ensuring documentation is complete and compliant with internal standards and regulatory requirements. • Respond to inquiries from brokers, underwriters, carrier partners, clients, and internal stakeholders in a professional and timely manner. • Assist with renewal activities, policy servicing, and other account management functions throughout the insurance lifecycle. • Collaborate with brokers, marketing professionals, and operational teams to support successful account execution and client service. • Utilize brokerage technology platforms, including AIM, ImageRight, Microsoft Excel, Outlook, and other business applications. • Support process improvement initiatives and assist with special projects as needed. • Participate in professional development opportunities, industry events, networking functions, and relationship-building activities with carrier and client partners. Qualifications Required • Bachelor's degree in Risk Management & Insurance, Business, Finance, Sales, Marketing, Communications, or a related field. • Active Property & Casualty license or willingness to obtain within the first 90 days of employment • Strong attention to detail and organizational skills. • Ability to manage multiple priorities in a fast-paced environment. • Excellent written and verbal communication skills. • Proficiency with Microsoft Office applications, including Excel and Outlook. • Demonstrated initiative, professionalism, and a desire to learn the insurance industry. Preferred • Internship, coursework, or professional experience in insurance, underwriting, brokerage, financial services, sales, customer service, account management, or related fields. • Familiarity with AIM, ImageRight, agency management systems, or other insurance technology platforms. • Experience utilizing AI-powered productivity tools such as Microsoft Copilot, Claude, ChatGPT, or similar solutions. • Property & Casualty insurance license or willingness to obtain upon hire. What You'll Gain • Hands-on training from experienced Casualty brokerage professionals. • Exposure to commercial insurance placements, underwriting strategy, carrier relationships, and client service. • A collaborative, energetic team environment that values learning, development, and professional growth. • Opportunities to attend industry networking events and build relationships with carrier and client partners. • Multiple long-term career paths, including brokerage operations, marketing, account management, and producer/broker roles. • The ability to build a rewarding career in the wholesale insurance industry while learning directly from experienced professionals. 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 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 hourly rate range for this position is $25.00 - $31.25 per hour. 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 HR@Ryansg.com 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.

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