AI-First Senior Engineer & Technical Leader

01460 Continental Casualty Company; Chicago (IL); On-site; USD 72,000 - 141,000; Full time

Job summary

CNA is seeking an AI-first engineering leader to define strategy, architect scalable cloud-native platforms, and guide enterprise teams across domain applications, APIs, and data pipelines. You will help set governance, standards, and a technical vision that aligns with business outcomes while mentoring managers and senior engineers.

The role requires hands-on experience with AI-assisted development tools (Claude, GitHub Copilot, Cursor), a strong background in microservices, CI/CD, security and

Qualifications

• 8+ years of software engineering experience.
• Experience driving AI-assisted development at scale.
• Experience defining standards, frameworks, and best practices.
• Ability to mentor teams and enable AI adoption across engineering organizations.
• Strong understanding of secure coding and compliance in AI-enabled environments.

Responsibilities

• Define and drive the AI-first engineering vision and strategy across development teams.
• Lead and mentor engineering teams in using AI tools effectively and responsibly.
• Establish governance models and best practices for AI-assisted development for quality, security and maintainability.
• Architect and deliver scalable, cloud-native and API-driven solutions across enterprise platforms.
• Guide teams in building production-grade applications using microservices, event-driven architectures, CI/CD.

Skills

AI Engineering

Technical Leadership

AI-assisted Development

Code Governance

Standards & Frameworks

Mentoring Teams

Secure Coding

Cloud-Native Architecture

Microservices & Distributed Systems

API-first & Event-driven

DevOps & CI/CD

Education

Bachelor’s degree in computer science or related discipline

Tools

Claude

GitHub Copilot

Cursor

Job description

CNA is seeking an AI-first engineering leader to define strategy, architect scalable cloud-native platforms, and guide enterprise teams across domain applications, APIs, and data pipelines. You will help set governance, standards, and a technical vision that aligns with business outcomes while mentoring managers and senior engineers.

The role requires hands-on experience with AI-assisted development tools (Claude, GitHub Copilot, Cursor), a strong background in microservices, CI/CD, security and