Director, AI Engineering and Automation (Remote)

Crum & Forster (C&F), with a proud history dating to 1822, provides specialty and standard commercial lines insurance products through our admitted and surplus lines insurance companies. C&F enjoys a financial strength rating of "A+" (Superior) by AM Best and is proud of our superior customer service platform. Our claims and risk engineering services are recognized as among the best in the industry.

Our most valuable asset is our people: more than 2500 employees in locations throughout the United States. The company is increasingly winning recognition as a great place to work, earning several workplace and wellness awards for four years running, including the 2025-2026 Great Place to Work® Award for our employee-first focus and our steadfast commitment to diversity, equity and Inclusion.

C&F is part of Fairfax Financial Holdings, a global, billion dollar organization.  For more information about Crum & Forster, please visit our website: www.cfins.com.

Director, AI Engineering & Automation

Overview

The Director, AI Engineering & Automation will lead the development and adoption of AI capabilities across the S&S Digital organization. This role is responsible for identifying opportunities to embed AI into underwriting, operations, digital platforms, and software development workflows.

The leader will build and manage a small, high-impact team focused on rapidly prototyping, operationalizing, and scaling AI solutions that improve productivity, automation, and decision-making across the enterprise.

This role focuses on practical application of AI technologies, including generative AI, large language models, intelligent agents, and developer productivity tools.

What you will do

• Lead the AI Engineering & Automation capability within the Digital organization
• Identify opportunities to embed AI into underwriting, submission processing, operations, and internal systems
• Drive adoption of AI-assisted development practices across engineering teams
• Develop AI copilots, automation tools, and internal knowledge assistants
• Partner with Digital, Data Science, Actuarial, and business stakeholders to deliver practical AI solutions
• Establish architecture and best practices for integrating AI into enterprise systems
• Lead rapid experimentation and prototyping of emerging AI capabilities
• Mentor AI engineers and promote AI adoption across the broader technology organization
• Ensure AI solutions align with security, governance, and compliance standards

What you will bring to C&F

• Bachelor’s or Master’s degree in Computer Science, Engineering, or related field
• 10+ years experience in software engineering, machine learning engineering, or AI systems
• Strong programming experience (Python preferred)
• Experience building production AI or ML systems
• Experience with LLM architectures, AI APIs, or AI agent frameworks
• Experience with cloud platforms (AWS preferred)
• Strong understanding of APIs, microservices, and distributed systems

Desired Skills

• Experience implementing AI-assisted software development tools
• Experience automating business workflows using AI
• Experience leading technical teams and influencing engineering culture
• Insurance industry experience

#LI-MS

#LI-REMOTE

• Competitive compensation package
• Generous 401K employer match
• Employee Stock Purchase plan with employer matching
• Generous Paid Time Off
• Excellent benefits that go beyond health, dental & vision. Our programs are focused on your whole family’s wellness, including your physical, mental and financial wellbeing
• A core C&F tenet is supporting your career development, so we provide a wealth of ways for you to keep learning, which may include tuition reimbursement, industry-related certifications and professional training to keep you progressing on your chosen path
• A dynamic, ambitious, fun and exciting work environment
• We believe you do well by doing good and want to encourage a spirit of social and community responsibility, matching donation program, volunteer opportunities, and an employee-driven corporate giving program that lets you participate and support your community

At C&F you will BELONG

If you require special accommodations, please let us know. We value inclusivity and diversity. We are committed to equal employment opportunity and welcome everyone regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, or Veteran status. If you require special accommodations, please let us know. Belonging at C&F, is a mindset. It’s about fostering a culture of inclusion and connection, where everyone feels valued, heard, and empowered to thrive and where our social impact efforts help strengthen the communities where we live and work.

For California Residents Only:  Information collected and processed as part of your career profile and any job applications you choose to submit are subject to our privacy notices and policies, visit https://www.cfins.com/onlineprivacypolicy/ca/noticeatcollection/  for more information.

Crum & Forster is committed to ensuring a workplace free from discriminatory pay disparities and complying with applicable pay equity laws.  Salary ranges are available for all positions at this location, taking into account roles with a comparable level of responsibility and impact in the relevant labor market and these salary ranges are regularly reviewed and adjusted in accordance with prevailing market conditions. The annualized base pay for the advertised position, located in the specified area, ranges from a minimum of $141,800 o a maximum of $236,400. The actual compensation is determined by various factors, including but not limited to the market pay for the jobs at each level, the responsibilities and skills required for each job, and the employee’s contribution (performance) in that role. To be considered within market range, a salary is at or above the minimum of the range. You may also have the opportunity to participate in discretionary equity (stock) based compensation and/or performance-based variable pay programs.