Principal AI Enablement & SDLC Coach

About the role

We are seeking a Principal AI-Native Enablement & Training Coach to lead the technical transformation and organizational change management for our engineering community. In this role, you will act as the architect of our developer 'Golden Path,' guiding engineering teams from manual coding execution toward an AI-augmented orchestration model using modern AI tools like Claude Code. You will bridge technical credibility with educational leadership to build a high-performing, AI-empowered software culture.

Location: Chicago, Illinois

Job type: Contract

Education: Bachelors

Responsibilities

• Design and deliver comprehensive training programs focused on AI-assisted development, context engineering, and iterative verification loops.
• Mentor and upskill engineering teams through workshops, peer-to-peer enablement sessions, and open office hours.
• Establish standard configurations and persistent AI guidelines (e.g., .claudecode , CLAUDE.md ) to align AI tools with enterprise engineering standards.
• Partner with AI Governance and Security teams to embed compliance rules, security guardrails, and automated quality gates into daily IDE workflows.

Requirements

• 15+ years of hands-on experience in full-stack software development with strong expertise in Java, Spring Boot, microservices, and React.
• Proven track record in technical coaching, developer enablement, or leading enterprise-level organizational change management.
• Practical experience utilizing AI-assisted development platforms (e.g., Claude Code, GitHub Copilot) and context engineering techniques.
• Exceptional presentation and communication skills, with the ability to engage both executive leadership and senior engineers effectively.

Qualifications

• Experience with cloud-native tooling, including Docker, Kubernetes, and modern CI/CD pipelines.
• Knowledge of custom AI extension frameworks, Model Context Protocol (MCP) servers, or custom guardrail integration.
• Strong background in Test-Driven Development (TDD) and automated software quality architecture.

Skills

• AI
• Cloud Native Architecture
• peer learning
• Containerization
• Docker
• modern Java
• Kubernetes
• microservices
• peer-to-peer
• React
• Spring Boot
• SDLC
• Test-Driven Development (TDD)
• Web APIs
• communication
• high emotional intelligence
• passion
• empathy
• architecture
• architecting
• Automation
• Organizational Change Management
• OCM
• Optimization Strategies