[Hiring] Director, AI Engineering and Automation @Crum & Forster

Role Description

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.

• 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

Qualifications

• 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

Requirements

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

Benefits

• 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, focused on whole family wellness
• Career development support, including tuition reimbursement and professional training
• A dynamic, ambitious, fun, and exciting work environment
• Encouragement of social and community responsibility through matching donation programs and volunteer opportunities