Full-Time

Underwriter 2

Updated on 9/11/2026

Ryan Specialty

Ryan Specialty

1,001-5,000 employees

Specialty insurance brokerages and underwriting programs

Compensation Overview

$85.9k - $100k/yr

+ Bonus

Chicago, IL, USA

In Person

Bachelor's

Category
Insurance (1)
Required Skills
Microsoft Office
Risk Management

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Requirements
  • A bachelor's degree in Risk Management, Business, Finance, Insurance, or a related field; equivalent experience will be considered.
  • At least 5 years of commercial property underwriting experience.
  • Strong understanding of property underwriting principles, policy structures, pricing methodologies, and risk assessment.
  • Experience evaluating complex commercial property risks.
  • Strong analytical, negotiation, and decision-making skills.
  • Excellent communication and relationship management abilities.
  • Proficiency with underwriting systems and Microsoft Office, along with data-driven decision-making.
Responsibilities
  • Underwrite and manage a portfolio of new and renewal property business.
  • Evaluate submissions, loss history, catastrophe modeling results, risk characteristics, and exposure data to make sound underwriting decisions.
  • Assess risk acceptability, coverage requirements, pricing adequacy, and policy structures.
  • Negotiate terms, conditions, deductibles, and pricing with brokers to achieve profitable growth objectives.
  • Develop and maintain strong relationships with wholesale and retail broker partners.
  • Drive new business production while maximizing retention within the assigned portfolio.
  • Collaborate with underwriting, brokerage, operations, claims, and carrier partners to deliver exceptional service.
  • Ensure underwriting decisions comply with company guidelines, carrier requirements, and regulatory standards.
  • Monitor portfolio performance and market trends to identify opportunities and emerging risks.
  • Assist in achieving production, profitability, and retention goals established by leadership.
Desired Qualifications
  • Experience working within an MGA, wholesale, E&S, or specialty insurance environment.
  • Experience underwriting catastrophe-exposed property risks.
  • CPCU, AU, ARM, or other insurance designations.
  • Knowledge of catastrophe modeling tools and property analytics platforms.

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 Jobs

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.