Full-Time

Director IT

Software Development

Deadline 7/22/27
AmTrust Financial

AmTrust Financial

1,001-5,000 employees

Multinational property and casualty insurer

Compensation Overview

$114.7k - $135k/yr

Cleveland, OH, USA

Hybrid

Hybrid role; in-office presence in Cleveland, OH; some remote work as needed.

Category
Engineering Management (1)
Requirements
  • Bachelor’s degree in Information Technology, Computer Science, Business Administration, or a related field.
  • Minimum of 5 years of experience in IT management or at least 5 years in a leadership role within the insurance industry, preferably in policy system technology.
  • Proven track record of successfully managing complex IT development delivery from inception to completion.
  • Experience with policy systems, data management, and analytics tools.
  • Strong leadership and team management skills, with the ability to inspire and motivate others.
  • Excellent project management skills, including planning, execution, and risk management.
  • Strong communication and interpersonal skills, with the ability to collaborate effectively with various stakeholders.
  • In-depth knowledge of IT infrastructure, applications, and emerging technologies relevant to policy maintenance.
  • Analytical mindset with the ability to leverage data to drive decision-making and process improvements.
  • Strong problem-solving skills and the ability to handle multiple priorities in a fast-paced environment.
  • Commitment to continuous learning and staying abreast of industry trends and best practices.
  • Strategic thinker with a vision for leveraging technology to achieve business objectives.
  • Results-oriented with a focus on delivering high-quality outcomes.
  • Adaptable and open to change, with a willingness to embrace new challenges and opportunities.
  • Customer-centric approach with a commitment to enhancing the CPP experience for policyholders.
  • Integrity and professionalism, with a strong ethical foundation.
Responsibilities
  • Lead the development, implementation, and maintenance of IT systems and applications that support the CPP application.
  • Collaborate with CPP management and other stakeholders to identify technology needs and develop strategic plans to meet those needs.
  • Oversee the integration of new technologies and systems into existing CPP processes, ensuring minimal disruption and maximum efficiency.
  • Manage a team of IT professionals, providing guidance, training, and support to ensure high performance and professional development.
  • Monitor system performance, troubleshoot issues, and implement solutions to enhance system reliability and user experience.
  • Ensure compliance with industry regulations and company policies regarding data security and privacy.
  • Collaborate with IT teams to integrate emerging technologies and best practices into CPP operations.
  • Ensure data integrity, accuracy, and security in compliance with industry regulations and company policies.
  • Lead and mentor a team of IT professionals, providing direction, support, and development opportunities.
  • Foster a culture of collaboration, innovation, and continuous improvement within the IT team.
  • Manage resource allocation and project prioritization to ensure the timely and successful delivery of IT initiatives.
  • Establish performance metrics and conduct regular evaluations to ensure team effectiveness and alignment with departmental goals.
  • Overseeing a team of about 15-20 Software Developers.
  • Plan, execute, and oversee IT projects related to CPP, including system upgrades, migrations, and integrations.
  • Develop project plans, timelines, and budgets, ensuring adherence to scope, schedule, and cost constraints.
  • Coordinate cross-functional teams and stakeholders to ensure project objectives are met and risks are mitigated.
  • Monitor project progress, provide regular status updates, and implement corrective actions as needed.
  • Act as a liaison between the CPP department and IT teams, ensuring clear communication and understanding of requirements and priorities.
  • Partner with business leaders to identify opportunities for IT-driven improvements in CPP operations.
  • Engage with external vendors and partners to evaluate and implement technological solutions that enhance CPP processing.
  • Represent the CPP IT function in leadership meetings and contribute to strategic decision-making.

AmTrust Financial Services provides property and casualty insurance for businesses through three global segments: Small Commercial Business Insurance, Specialty Risk and Extended Warranty, and Specialty Middle-Market Property and Casualty Program Insurance. Its products work by underwriting and issuing workers’ compensation, general liability, and other specialty coverages tailored to the size and risk profile of small to mid-sized businesses, with policy administration and claims handled within its program structures. The company differentiates itself by targeting niche markets with program-style insurance and a global, diversified mix of standard and specialty coverages. Its goal is to protect businesses from P&C risks while growing market share across its global segments and expanding its specialized programs to new customers and regions.

Company Size

1,001-5,000

Company Stage

N/A

Total Funding

$246.1M

Headquarters

New York City, New York

Founded

1998

Simplify Jobs

Simplify's Take

What believers are saying

  • AmTrust recognized as 2026 Best and Brightest Company for employee engagement.
  • Andi Stroud appointed SVP for Georgia, leveraging 30+ years expertise.
  • AmTrust declares quarterly cash dividends on preferred stock.

What critics are saying

  • Fidelity National acquires First Nationwide commercial operations, eroding title revenue.
  • Blackstone spins off MGAs into ANV Group, stripping high-margin fees.
  • Repeated MGA divestitures signal shareholder pressure for full privatization.

What makes AmTrust Financial unique

  • AmTrust launches E&S Premier group with Curt Fletcher and Matt Thomas leading.
  • AmTrust expands E&S division into property, environmental, and builders risk lines.
  • AmTrust partners with Trawick International to innovate travel insurance products.

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People at AmTrust Financial who can refer or advise you

Benefits

Health Insurance

Dental Insurance

Life Insurance

401(k) Retirement Plan

401(k) Company Match

Paid Time Off

Company News

Business Wire
Feb 10th, 2026
AmTrust International launches APRA-licensed insurer in Australia to expand legal expenses coverage

AmTrust International has launched AmTrust Specialty Limited, an APRA-licenced entity in Australia, marking a significant expansion for the global specialty insurer. The move enables the company to scale its Legal Expenses Insurance offering in response to consistent demand from intermediaries, funders and legal professionals. The company will provide After the Event and Before the Event insurance products, supporting individuals and businesses pursuing or defending legal action by covering financial risks. These products will be distributed through insurance intermediaries, litigation funders and solicitors. AmTrust International, a subsidiary of AmTrust Financial Services, specialises in property, mortgage and credit, warranty, professional lines, legal expenses and medical malpractice insurance. The Australian launch reflects the company's long-term commitment to building a sustainable presence in the country's mature legal landscape.

Insurance Journal
Sep 17th, 2025
People Moves: AmTrust Names Fletcher and Thomas to Lead New E&S Premier Group; The Fidelis Partnership Makes Leadership Promotions

AmTrust Financial Services Inc., headquartered in New York City, appointed Curt Fletcher as senior vice president and Matt Thomas as vice president of AmTrust's newly established E&S Premier group within the company's excess and surplus (E&S) division.

Insurance Journal
Sep 16th, 2025
AmTrust Expands E&S Division, Spins Off Some MGAs With Blackstone

AmTrust Financial Services has a busy day on Sept. 15 as it expanded its excess & surplus division to include new lines, appointed leadership, and announced an agreement with Blackstone Credit & Insurance to spin off certain managing general agencies into a new, independent company.

WorkCompWire
Sep 5th, 2025
AmTrust Names Carl Canales EVP, Head of Field Operations for North American P&C

New York, NY - AmTrust Financial Services, Inc., recently announced the appointment of Carl Canales as Executive Vice President (EVP), Head of Field Operations for North American P&C.

The Manila Times
Jul 29th, 2025
Trawick International Announces Strategic Partnership with AmTrust to Enhance Travel Insurance Offerings

By combining Trawick's deep market expertise with AmTrust's industry-leading underwriting capabilities, the partnership will fuel the development of innovative trip cancellation and travel protection plans that better serve today's travelers.