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This position has closed. Ryan Specialty removed this listing from their careers page on Oct 6, 2026. The interview prep below is still useful, and there are similar open roles at the bottom of this page.

Healthcare Insurance - Stop Loss Modeler

Ryan Specialty · Remote · $112,000–$140,000 a year · Full time

Posted Aug 28, 2026 · We last checked this listing on Oct 5, 2026

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 an Excel tool you built or improved that saved people time.

What they are checking: Whether they can automate and standardize tools that others rely on.

Tell me about a time you found an error in your own model after it was in use.

What they are checking: Whether they own mistakes and fix them openly, which protects pricing decisions.

What would you do

An underwriter says the rate calculator is giving numbers that look wrong. What do you do?

What they are checking: Whether they investigate quickly and communicate clearly while fixing the issue.

Actuarial and Sales want different things from a report. How do you handle it?

What they are checking: Whether they can gather requirements and build tools that serve several groups.

About the work

Walk me through how you'd build a rating model for a specific stop-loss quote.

What they are checking: Whether they understand how claims data, trend and attachment points drive stop-loss pricing.

How do you check that a financial model's output matches the source data?

What they are checking: Whether they have real quality-check habits for models used in pricing.

What's the difference between specific and aggregate stop-loss coverage?

What they are checking: Whether they have the basic product knowledge needed to model these programs.

How would you use AI to speed up checks or calculations in an Excel-based rating process?

What they are checking: Whether they can apply new tools thoughtfully while keeping results reliable.

How do you document a model so someone else can use and maintain it?

What they are checking: Whether they create documentation that keeps tools usable after handoff.

What portfolio-level metrics would you track for a stop-loss or captive program?

What they are checking: Whether they know which numbers show if a program is healthy.

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.

Practice this out loud

The full job description

As published by Ryan Specialty.

Position Summary This role is responsible for building, maintaining, and improving the financial tools and models that support pricing, rating, and reporting for our stop-loss, reinsurance, and captive programs. This role will collaborate with the actuarial and underwriting teams in support of our goals What will your job entail? Job Responsibilities: • Build, maintain, and improve financial models and analytical tools supporting actuarial pricing, manual rating, and reporting for stop-loss, reinsurance, and captive programs • Translate the data currently being collected into usable and actionable initiatives, and assist with the development, collection, organization, and reporting of additional data meaningful for the firm • Support initiatives to automate and standardize Excel-based tools, including the application of AI to speed up calculations, quality checks, and data organization • Update and maintain rating templates and rate calculators used by the underwriting team for new and renewal business • Perform quality checks and validate the outputs of financial models against source data • Assist in tracking cost drivers, trends, and portfolio-level metrics across stop-loss and captive programs • Collaborate with actuarial, underwriting, finance and sales teams to gather requirements for tools, templates, and reports • Prepare and maintain clear documentation for financial models, tools, and related processes • Support ad hoc data requests and analyses for the Chief Actuary and Actuarial Directors • Maintain and expand working knowledge of healthcare reinsurance, stop-loss, and captive insurance concepts Education/Experience/Skills: • Bachelor's degree in finance, mathematics, statistics, economics, or a related field • 5 years of relevant experience in financial modeling, data analysis, or a similar function • Background in healthcare reinsurance, stop-loss, and/or captive insurance strongly preferred • Advanced Excel skills, with experience building and maintaining complex workbooks, financial models, and related analytical tools • Experience using AI tools (e.g., Claude, ChatGPT) to support data analysis, modeling, or process improvement will be heavily weighted • Familiarity with data manipulation and analytics tools (e.g., SQL, Power BI, Tableau) a plus • Strong attention to detail and accuracy • Strong interpersonal skills (written and verbal) • Committed team player, comfortable supporting senior actuarial staff as needed • Ability to manage multiple priorities and work independently 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 $112,000.00 - $140,000.00 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.