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Connector Underwriting Associate

Ryan Specialty · Chicago, IL · $64,000–$80,000 a year · Full time

Posted Sep 17, 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 caught an error before it reached a customer.

What they are checking: Whether they have the attention to detail binding operations require.

How do you handle a high volume of policy transactions without losing accuracy?

What they are checking: Whether they use routines and checks to keep quality steady at volume.

How do you stay organized when you're supporting several carriers with different guidelines?

What they are checking: Whether they can track varying requirements accurately across many carriers.

What would you do

RT Connector issues policies with a click. Where do you think errors are most likely in that process?

What they are checking: Whether they think about how automation can hide mistakes and where a human check adds value.

A retail agent needs a policy bound today but a required document is missing. What do you do?

What they are checking: Whether they hold to binding requirements while helping the agent fix the gap quickly.

An agent calls upset that their policy documents are wrong. How do you handle it?

What they are checking: Whether they own the fix and communicate clearly with retail partners.

If you saw the same binding issue happening repeatedly, what would you do?

What they are checking: Whether they raise process problems so the team can fix the root cause.

About the work

Walk me through what you check before binding a policy to make sure it follows underwriting guidelines.

What they are checking: Whether they know the key checks on subjectivities, eligibility and quoted terms before coverage is bound.

What's the difference between E&S and admitted insurance, and why does it matter for small commercial business?

What they are checking: Whether they understand the excess and surplus market and its filing and tax requirements.

What are surplus lines tax and filing requirements, and who is responsible for them?

What they are checking: Whether they understand regulatory steps that make an E&S policy compliant.

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 RT Connector allows retail insurance agents to efficiently access multiple lines of coverage from multiple carriers for their E&S small commercial business. Through one single, streamlined application, RT Connector offers bindable quotes from multiple carriers and will issue policies with the click of a button. The Connector Underwriting Associate is a pivotal role within the RT Connector support team environment, focusing on the efficient and quality-driven management of binding operations. This individual is responsible for overseeing the binding process, ensuring that all printed materials are finished to the highest standards and meet customer specifications. What will your job entail? • Assists the process of binding insurance policies, ensuring accuracy and compliance with binding underwriting guidelines and regulatory requirements. • Employ expertise to execute complex tasks ensuring maximum efficiency and effectiveness. • Act as a training resource, mentoring and guiding team members to foster skill development and optimize performance. • Evaluates renewals, new business and endorsements according to guidelines outlined in the business requirements documents and within their authority level. • Manages underwriting applications with the information necessary to rate, document and issue accurate and compliant policies. • Reviews and processes policy endorsements, including changes to coverage, limits, or policy terms, ensuring accuracy and timely implementation and tracks cancellation notifications, non- renewal, and renewal solicitation notifications. • Review inspection reports to assess risk quality and to confirm exposure base accuracy. • Maintains comprehensive and organized records of all binding transactions and related documentation, including policy details, endorsements, and client information. • Communicates with clients to collect required information, explains policy terms and conditions, and addresses any questions or concerns related to the binding process. • Executes the work assigned by the Connector activity workgroup in the standard service timeline. • Collaborate with other underwriting team members, Support, and Product Managers to gain a comprehensive understanding of the Connector processes and workflows. • Provides feedback to internal team members regarding trends and efficiency opportunities. • Assists the Connector team with any ad hoc tasks and special requests as needed. Work Experience: • Minimum of 5-7 years of work experience in Insurance Industry or Binding Underwriting. • Preferred experience in Excess & Surplus Lines • Preferred experience as an Underwriter Associate • Preferred experience in ConceptOne Education: • Bachelor's degree required; Risk Management and Insurance Business Administration, Business Operations and Sales preferred. • Any other related discipline or commensurate work experience considered. Licenses & Certifications: • Preferred: Active designation from Risk & Insurance Education Alliance or The Institutes • ***** Applicants must be authorized to work for any employer in the U.S. We are unable to sponsor or take over sponsorship of an employment visa at this time***** 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 salary range for this position is $64,000.00 - $80,000.00 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 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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