Full-Time

Microsoft Systems Engineer

Posted on 9/9/2025

Ryan Specialty

Ryan Specialty

1,001-5,000 employees

Specialty insurance brokerages and underwriting programs

Compensation Overview

$104k - $130k/yr

+ Bonus

No H1B Sponsorship

Cheektowaga, NY, USA + 3 more

More locations: Chicago, IL, USA | Carmel, IN, USA | Kansas City, MO, USA

In Person

Category
IT & Security (1)
Required Skills
PowerShell
Microsoft Azure
Requirements
  • Degree in Management Information System, Computer Science or a comparable technical degree.
  • Minimum of 10 years of hands-on experience with enterprise networks, email systems and telecom systems.
  • Experience with Microsoft Exchange, Microsoft server operating systems, Azure Cloud computing, Azure computer/storage, AVD, VMWare, Office 365/Azure AD administration, and Intune/SCCM/WSUS or equivalent experience is required.
  • Extensive PowerShell scripting knowledge
  • Ability to work in a fast-paced environment
  • Willingness to ‘do what it takes’ to deliver as needed
  • Excellent interpersonal skills
  • Exceptionally self-motivated and directed
  • Keen attention to detail
Responsibilities
  • Provide governance for a stable and responsive server environment that supports all the needs of the business and our application development and support teams.
  • Create redundancy for all key infrastructure systems.
  • Work with the application support teams to provide the infrastructure required to create application redundancy for our key business applications.
  • Enhance our Infrastructure monitoring and observability.
  • Implement system automations for enhanced efficiency.
  • Develop processes to streamline the successful integration of acquisitions.
  • Maintain technical documentation for supported systems.
  • Provide technical training and knowledge transfer to junior team members.
  • Participation in an on-call rotation schedule as requested.
  • 10% Travel as necessary.

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.

INACTIVE