Director, AI Engineering and Automation (Remote)

Crum & Forster • Morristown, NJ

13h • Remote

About The Position

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.

Requirements

• 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

Nice To Haves

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

Responsibilities

• 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

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. 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

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Number of Employees: 501-1,000 employees