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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.

AI Delivery Lead-RT Specialty

Ryan Specialty · Chicago, IL · $140,000–$175,000 a year · Full time

Posted Aug 21, 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 AI solution you built hands-on alongside business users. What did you build and what was your part?

What they are checking: Whether they can actually build, since the posting expects solutioning work and not just managing delivery.

Tell me about a time a business leader wanted something from AI that it couldn't reliably do. How did you handle that conversation?

What they are checking: Whether they can set honest expectations with senior people without losing their trust or support.

Tell me about a project you led where the technology worked but people didn't adopt it. What did you learn?

What they are checking: Whether they see adoption and change management as part of delivery rather than someone else's problem.

What would you do

Requests are coming from business customers, Forward Deployed Engineers and front-office Vibe Coders all at once. How do you decide what gets built first?

What they are checking: Whether they can prioritize across very different requesters in a way people accept as fair and tied to strategy.

A broker built a tool on their own that uses client data and is now sharing it with their team. What do you do?

What they are checking: Whether they can bring citizen-built AI under governance without killing the enthusiasm that produced it.

You have more good AI ideas than engineers. How do you keep the people whose requests are waiting from losing interest?

What they are checking: Whether they can manage a backlog transparently so the intake process keeps its credibility with the business.

Describe how you'd explain the status of the AI Innovation Center's portfolio to division leadership in fifteen minutes.

What they are checking: Whether they can turn a messy portfolio of projects into a clear, honest picture leaders can make decisions from.

About the work

You own all AI intake for the division. Walk me through how you'd triage a new request that comes in from a front-office team.

What they are checking: Whether they have a clear method for judging value, feasibility and risk before committing scarce engineering time.

In a wholesale specialty insurance business, where do you think AI could make the biggest real difference for brokers, and where would you be careful?

What they are checking: Whether they understand the insurance workflow well enough to separate useful use cases from risky or shallow ones.

How do you decide whether an AI pilot has worked well enough to scale, or should be stopped?

What they are checking: Whether they define success measures up front and are willing to end projects that are not delivering.

What delivery governance would you put in place for AI work that touches client data, pricing or underwriting submissions?

What they are checking: Whether they think about data privacy, accuracy checks and accountability before an AI tool reaches production use.

Practice this interview out loud.

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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 AI Delivery Lead serves as the central orchestrator of RT Specialty’s AI Innovation Center, owning the end-to-end intake, triage, and delivery governance of AI initiatives across the division. This role partners with business leaders, engineers, and front-office users to ensure that every AI opportunity is assessed, resourced, and executed in alignment with RT’s strategic objectives. What will your job entail? Responsibilities • Own divisional AI intake: serve as the primary point of contact for all incoming AI opportunity requests from business customers, Forward Deployed Engineers, and front-office Vibe Coders. • Provide hands-on solutioning support for front-office teams where no suitable solutioning is available, actively building AI solutions alongside business users rather than simply managing their delivery. • Drive innovation and cutting-edge results in the creation of usable, applicable and transformational processes and applications with AI. • Consistently evaluate AI tools and vendors to ensure RT’s position as the leader in available resources inside and outside the firm. • Facilitate triage sessions in partnership with the RT COO, CIO, RT Transformation, Portfolio Manager, Architecture, and OCM Director to assess each incoming idea for AI build viability, strategic alignment, and optimal delivery pattern. • Guide talent pool allocation by matching initiatives to the appropriate resources based on complexity, architectural significance, and enterprise standards requirements. • Continuously assess whether in-flight initiatives remain appropriately classified as scope and complexity evolve, re-routing resources as needed. • Maintain and communicate the AI product backlog, ensuring deferred ideas are logged, prioritized, and revisited as resources and strategic conditions change. • Prevent redundant AI initiatives by maintaining awareness of all active projects across front-office teams and facilitating collaboration where use cases overlap. • Partner with the Portfolio Manager to connect the AI initiative portfolio to the broader PMO portfolio, ensuring dependencies are visible and governance is applied consistently. Requirements • AI Initiative Management – You have hands-on experience managing AI or technology initiatives from intake through delivery, with a demonstrated ability to assess use case viability and match solutions to the right delivery approach. • Applied AI Fluency – Comfort evaluating the feasibility of AI and automation use cases without necessarily building them yourself. Familiarity with low-code/no-code AI tooling, Vibe Coding platforms, and when to escalate to engineering resources. • Cross-functional Facilitation – Proven ability to lead structured decision-making sessions with diverse stakeholders (technology, operations, compliance, senior leadership) and drive to clear, documented outcomes. • Strategic Prioritization – Skilled at evaluating competing demands against organizational strategy, resource constraints, and interdependencies to make and communicate clear prioritization decisions. • Bachelor’s or Master’s degree in a relevant field (e.g. Computer Science, Engineering, Business), and/or relevant industry experience • Bachelor's degree and at least 3 years of enterprise technology deployment OCM experience OR a High School Diploma / GED and at least 7 years of OCM experience • Experience in insurance processes is desired. • Experience in participating in cross-functional projects and influencing key stakeholders. • Experience in engaging individuals, teams, and leadership to drive successful change. • Excellent written, verbal, and presentation skills • Demonstrated organizational, business process and project management skills. • Intellectual curiosity and the ability to quickly learn. • Comfort working at a fast pace and with ambiguity. • Serious attention to detail and proven ability to manage multiple, competing priorities. • Keen emotional intelligence • ***** 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 $140,000.00 - $175,000.00 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.