Full-Time

Structured Insurance Director of Casualty

Posted on 4/18/2026

Ryan Specialty

Ryan Specialty

1,001-5,000 employees

Specialty insurance brokerages and underwriting programs

Compensation Overview

$200k - $250k/yr

+ Bonus

New York, NY, USA

In Person

Category
Finance & Banking (1)
Required Skills
Risk Management
Requirements
  • Minimum 8 years of property and casualty underwriting, with significant exposure to complex/structured solutions.
  • Bachelor’s degree required (Risk Management, Actuarial Science, or Business Administration preferred). Equivalent experience considered.
  • State P&C and/or surplus lines licenses required.
Responsibilities
  • Report to Chief Underwriting Officer.
  • Oversee underwriting strategy and workflows for structured casualty opportunities, including casualty program business.
  • Lead development and implementation of casualty coverage strategy, forms, and pricing concepts.
  • Lead the underwriting and development of bespoke structured casualty solutions for complex risks, focusing on profitable growth and long-term sustainability.
  • Together with casualty underwriting team, evaluate, select, and price risks, and develop solutions utilizing structuring techniques while ensuring compliance with underwriting guidelines, carrier standards, and legal and regulatory requirements.
  • Manage portfolio retention, renewal strategies, and active monitoring of complex property and casualty accounts, focusing on portfolio growth that balances with risk assumption metrics.
  • Manage team activity to assure timely review of submissions with casualty team, delivery comprehensive and well-crafted underwriting proposals, and delivery of insurance or captive reinsurance documentation, including rate, quote, and bind processing, premium management, and delivery of policies and endorsements.
  • Lead development and rollout of new traditional and structured casualty risk products, as well as developments of existing underwriting methodology, forms, and structures.
  • Lead comprehensive risk assessments focusing on client’s risk, including coverage, exposure, safety features, and industry.
  • Oversee casualty team underwriting activities to assure that individual and group standards are consistently achieved.
  • Determine and implement appropriate insurance and captive reinsurance structures, including setting of limits, premiums, and terms for structured casualty solutions.
  • Lead negotiations of bespoke terms and conditions with brokers while identifying cross-selling opportunities.
  • Analyze, report on, and help manage risk portfolio.
  • Optimize available data to assist in development of strategies and pricing for different risk structures and product types and adjust underwriting strategies accordingly with senior underwriting leadership.
  • Build and maintain long-term professional relationships with brokers, carriers, captive managers, and corporate clients, while enabling casualty underwriting team to similarly manage such relationships.
  • Coordinate industry events, and Represent the company and affiliates at industry event.
  • Understand emerging market trends and regulatory developments and incorporate recommended and required changes into company processes together company leadership.
  • Develop strategic initiatives to secure new business opportunities and assure renewals to expand the structured casualty portfolio while assuring profitability of the casualty portfolio.
  • Provide mentorship and training to underwriters, ensuring technical excellence, adherence to goals and guidelines, and effective use of systems.
  • Partner with internal teams to optimize processes, integrate new risk solution concepts, technologies, and align departmental goals with global business objectives.
  • Set premium forecasts and budgets, assist in management performance reporting.
Desired Qualifications
  • CPCU, CIC, or equivalent advanced certifications.

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

Simplify Jobs

Simplify's Take

What believers are saying

  • Organic revenue grows 13.5% with 21.2% annual revenue and 19.2% free cash flow margin.
  • Acquires SSRU, 360 Underwriting, and Innovisk to expand Canadian, Irish, and P&C capacity.
  • Raises $400M reinsurance sidecar for $900M multi-year premium in cat risks.

What critics are saying

  • Integration failures from 2024-2025 acquisitions overload operations and dilute focus.
  • MediaAlpha's 69.4% growth bypasses brokers, eroding wholesale margins.
  • $600M notes strain cash flow amid rising rates, limiting reinvestment.

What makes Ryan Specialty unique

  • Ryan Specialty channels complex risks via Wholesale Brokerage, Binding Authority, and Underwriting Management segments.
  • RT Specialty leads as second-largest US wholesale broker with $2.4B 2024 revenue.
  • Specializes in E&S lines like property, casualty, and workers' compensation for hard-to-place risks.

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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

8%

1 year growth

8%

2 year growth

9%
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.ca
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.

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