Full-Time

Property and Casualty Underwriting Director

Posted on 2/21/2026

Ryan Specialty

Ryan Specialty

1,001-5,000 employees

Specialty insurance brokerages and underwriting programs

Compensation Overview

$128.4k/yr

+ Bonus

Middletown, NY, USA

In Person

Category
Finance & Banking (1)
Required Skills
Risk Management
Data Analysis
Requirements
  • Bachelor’s degree or Master’s in Risk Management, Actuarial or Business Administration required. Any other related discipline or commensurate work experience considered.
  • 12+ years of experience in Property and Casualty insurance underwriting.
  • 5+ years of management experience.
  • State property and casualty and/or surplus line license is required.
Responsibilities
  • Directs and oversees the comprehensive underwriting process for both new and renewed property and casualty accounts to achieve and exceed profitability targets.
  • Partners with executives and business heads to craft a compelling underwriting strategy, outlines ambitious revenue targets and market expansion plans.
  • Translates the strategic vision of the executives into actionable long-term and short-term plans for the underwriting business, ensuring teams and functions are aligned across the organization.
  • Leads the development of innovative property and casualty products within the underwriting portfolio, leveraging market insights, customer needs, and emerging industry trends.
  • Reviews and authorizes innovative underwriting solutions and structures and recommends changes as needed to deliver business goals.
  • Supervises strategic initiatives and ensures data driven decision making, operational excellence and improved client retention in alignment with Ryan Specialty's vision and objectives.
  • Identifies areas for growth and cross-selling, fosters an innovative culture and drives the team to develop new underwriting practices, guidelines, and processes for increased effectiveness.
  • Oversees comprehensive risk analysis, evaluates factors such as coverage value, location, usage, safety features to make informed decisions on risk acceptance, modification, or decline.
  • Establishes and enforces consistent underwriting best practices within the team, aligning with underwriting guidelines to ensure rating, pricing, profitability, and structuring adequacy.
  • Establishes strong relationships with key brokers, clients, and other stakeholders aimed at growing the business.
  • Provides training and mentorship to underwriting professionals, focusing on underwriting approaches, compliance, policy documentation, administration, and other best practices.
Desired Qualifications
  • Chartered Property Casualty Underwriter (CPCU) or Associate in Risk Management (ARM) a plus

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

  • 21.2% annual revenue growth and 19.2% free cash flow margin drive scalability.
  • $400M reinsurance sidecar provides $900M multi-year P&C capacity.
  • Acquisitions like Innovisk expand revenue by $58M annually.

What critics are saying

  • Six acquisitions in 18 months cause integration failures and cultural clashes.
  • $600M senior notes strain cash flow if rates rise or losses hit.
  • Digital platforms like MediaAlpha bypass brokers, cutting RT commissions 15-20%.

What makes Ryan Specialty unique

  • RT Specialty intermediates complex specialty risks across all 50 states.
  • Binding Authority enables delegated quoting and policy binding for carriers.
  • Underwriting Managers develop proprietary programs for niche industries.

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Benefits

Paid Vacation

Paid Sick Leave

Paid Holidays

Paid Parental Leave

Mental Health Support

Company News

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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