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Ryan Specialty

Ryan Specialty

Specialty insurance brokerages and underwriting programs

AI Delivery Lead - RT Specialty

Full-Time
$140k - $175k/yr

+ Bonus

Mid
Bachelor's, Master's
Chicago, IL, USA
In Person
No H1B Sponsorship

About the job

Requirements
  • Hands-on experience managing AI or technology initiatives from intake through delivery, including assessing use case viability and matching solutions to the appropriate delivery approach.
  • Familiarity with low-code/no-code AI tooling and Vibe Coding platforms, including knowing when to escalate work to engineering resources.
  • Proven ability to lead structured decision-making sessions with technology, operations, compliance, and senior leadership stakeholders and drive clear, documented outcomes.
  • Ability to evaluate competing demands against organizational strategy, resource constraints, and interdependencies and communicate prioritization decisions.
  • A Bachelor's or Master's degree in a relevant field such as Computer Science, Engineering, or Business, and/or relevant industry experience.
  • At least 3 years of enterprise technology deployment organizational change management experience with a bachelor's degree, or at least 7 years of organizational change management experience with a high school diploma or GED.
  • Experience participating in cross-functional projects and influencing key stakeholders.
  • Experience engaging individuals, teams, and leadership to drive successful change.
  • Excellent written, verbal, and presentation skills.
  • Organizational, business process, and project management skills.
  • Ability to quickly learn.
  • Ability to work at a fast pace and with ambiguity.
  • Serious attention to detail and ability to manage multiple, competing priorities.
  • Keen emotional intelligence.
  • Must be authorized to work for any employer in the United States.
Responsibilities
  • Own divisional AI intake as the primary point of contact for incoming AI opportunity requests from business customers, Forward Deployed Engineers, and front-office Vibe Coders.
  • Provide hands-on solutioning support for front-office teams by actively building AI solutions alongside business users when no suitable solution is available.
  • Create usable, applicable, and transformational AI-enabled processes and applications.
  • Evaluate AI tools and vendors to maintain access to leading internal and external resources.
  • Facilitate triage sessions with the RT COO, CIO, RT Transformation, Portfolio Manager, Architecture, and OCM Director to assess AI build viability, strategic alignment, and delivery approach.
  • Guide talent-pool allocation by matching initiatives to resources based on complexity, architectural significance, and enterprise standards requirements.
  • Reassess the classification of in-flight initiatives as scope and complexity evolve and reroute resources as needed.
  • Maintain and communicate the AI product backlog, logging, prioritizing, and revisiting deferred ideas as resources and strategic conditions change.
  • Prevent redundant AI initiatives by tracking active front-office projects and facilitating collaboration when use cases overlap.
  • Partner with the Portfolio Manager to connect the AI initiative portfolio to the broader PMO portfolio, making dependencies visible and applying governance consistently.
Desired Qualifications
  • Experience with insurance processes.

About the company

Ryan Specialty provides specialty insurance products and solutions to insurance brokers, agents, and carriers. It operates through three segments: Wholesale Brokerage (RT Specialty) to place complex risks, Binding Authority for managing general underwriters to quote and service policies, and Underwriting Management to develop proprietary programs under delegated authority. The company differentiates itself by combining broker access, delegated underwriting authority, and proprietary programs to serve hard-to-place risks, with a strong US presence and international reach. Its goal is to deliver tailored risk solutions for specialty and hard-to-place risks while expanding its international specialty insurance market.

Company Size

1,001-5,000

Company Stage

IPO

Headquarters

Chicago, Illinois

Founded

2010

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Simplify's Take

What believers are saying

  • Q2 2026 revenue rose 7.2% to $916.6 million; adjusted EPS grew 12.1%.
  • 2025 revenue crossed $3 billion, with 10.1% organic growth and 15 straight growth years.
  • A $300 million buyback and 8% dividend hike signal strong cash generation.

What critics are saying

  • Q2 2026 net income fell 13.1%, while margin slipped to 35.7%.
  • Empower charges $160 million through 2028, with 95% requiring cash.
  • Property pricing fell 25%-35% on large accounts in Q4 2025, pressuring 2026 growth.

What makes Ryan Specialty unique

  • Ryan Specialty's delegated-authority platform generated $1.4 billion revenue in 2025, 47% of total.
  • Empower Program targets brokerage, binding, and underwriting integration across specialties by 2028.
  • RAC Re and AXIS-Lloyd's partnerships expand specialty catastrophe capacity and underwriting control.

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Benefits

Paid Vacation

Paid Sick Leave

Paid Holidays

Paid Parental Leave

Mental Health Support

Growth & Insights and Company News

Headcount

6 month growth

16%

1 year growth

16%

2 year growth

18%
Yahoo Finance
Mar 11th, 2026
Ryan Specialty and MediaAlpha are small-cap stocks to target, while EverQuote lags behind

MediaAlpha, an insurance marketplace technology platform, has demonstrated strong momentum with 69.4% annual revenue growth over the past two years. The company, which connects insurance carriers with consumers, is trading at a market capitalisation of $544.6 million. The platform processes nearly 10 million consumer referrals monthly across property, casualty, health and life insurance products. Forecasted revenue growth of 11.8% for the next 12 months suggests sustained momentum. Earnings per share growth of 564% annually has significantly outpaced revenue expansion, indicating improving profitability as the business scales. Ryan Specialty, a wholesale insurance broker founded in 2010, posted impressive metrics including 21.2% annual revenue growth and a robust 19.2% free cash flow margin. The company trades at $4.73 billion market capitalisation.

Yahoo Finance
Feb 3rd, 2026
Ryan Specialty tops Wall Street picks with 36% upside, while Mister Car Wash and Donnelley Financial face headwinds

Ryan Specialty, a wholesale insurance broker founded in 2010, is attracting Wall Street attention with a consensus price target of $64.31, implying 35.5% upside. The company has demonstrated strong organic revenue growth averaging 12.8% over the past two years. Ryan Specialty's earnings per share grew 23.1% annually over the last two years, significantly outpacing peers. The company maintains a robust free cash flow margin of 18.9%, enabling consistent capital reinvestment and returns. Meanwhile, analysts remain bullish on Mister Car Wash and Donnelley Financial Solutions despite concerning fundamentals. Mister Car Wash faces weak same-store sales trends and high debt levels, whilst Donnelley Financial Solutions has seen sales decline 3% annually over five years. Independent analysis suggests caution on these stocks despite Wall Street's optimistic price targets.

Insurance Canada
Nov 7th, 2025
Ryan Specialty Acquires Stewart Specialty Risk

Ryan Specialty has signed a definitive agreement to acquire Stewart Specialty Risk Underwriting Ltd. (SSRU), a Canadian managing general underwriter based in Toronto. SSRU, founded in 2016 by Stephen Stewart, specializes in high-hazard property and casualty solutions and will join the Ryan Specialty Underwriting Managers division. SSRU has a strong distribution network across all 13 Canadian provinces and territories.

Artemis
Sep 5th, 2025
Ryan Specialty raises $400M reinsurance sidecar

Ryan Specialty launched a collateralized reinsurance sidecar, Ryan Alternative Capital Re, Ltd., raising $400 million, backed by Flexpoint Ford and Sixth Street. This vehicle supports Ryan Specialty Underwriting Managers' P&C insurance business, providing $900 million in multi-year premium capacity. The initiative, in collaboration with AXIS Capital and Lloyd's of London, aims to enhance specialty cat and non-cat risk capacity. Deutsche Bank Securities acted as the structuring and placement agent.

Business Wire
May 21st, 2025
Ryan Specialty Acquires 360° Underwriting

Ryan Specialty enters Ireland with acquisition of 360 Underwriting.