Principal AI Enablement & SDLC Coach
Insurance Industry | Chicago, IL Preferred (Remote CST/EST Considered)
Location
- Chicago, IL preferred
- Remote candidates in CST or EST time zones will be considered for the right experience
- Long-term contract opportunity with potential for extensions
About the Opportunity
Our client, a leading organization within the insurance industry, is seeking a Principal AI Enablement & SDLC Coach to lead the next evolution of software engineering through AI-native development practices.
This is a unique opportunity for a senior-level technologist who combines deep software engineering expertise with a passion for coaching, organizational transformation, and developer enablement. You will serve as a trusted advisor to engineering teams, helping modernize software delivery by guiding developers from traditional coding workflows toward AI-augmented software orchestration using Claude Code and other emerging AI technologies.
The ideal candidate brings principal-level engineering experience, strong communication skills, and the credibility to engage senior developers, architects, engineering leaders, and executives.
Key Responsibilities
Lead AI Transformation Across Engineering
- Drive adoption of AI-native software development methodologies across engineering teams.
- Coach developers on transitioning from manual execution to AI-assisted orchestration and accelerated software delivery.
- Facilitate formal training sessions, workshops, office hours, and peer-learning communities.
Develop Enterprise Training Programs
- Design and deliver comprehensive learning paths focused on Claude Code, context engineering, agentic workflows, and AI-assisted development patterns.
- Build training materials and enablement resources that improve developer productivity while maintaining quality and governance standards.
Design Career Evolution Paths
- Partner with engineering leadership and stakeholders to define role-specific AI adoption journeys.
- Help developers understand how responsibilities evolve within AI-augmented engineering environments.
Establish AI Development Standards
- Educate teams on enterprise AI configurations, including Claude project structures, persistent context management, and reusable skill frameworks.
- Promote consistent engineering practices and governance-aligned AI usage.
Partner with Engineering Excellence & AI Governance
- Incorporate security, compliance, governance, and organizational policies into day-to-day developer workflows.
- Collaborate with architecture, security, and platform teams to encourage responsible AI adoption.
Foster Communities of Practice
- Build and lead internal communities focused on AI engineering excellence.
- Create forums that encourage collaboration, knowledge sharing, and continuous learning.
Improve Requirements & SDLC Practices
- Teach engineering teams how to leverage AI to refine user stories, acceptance criteria, technical designs, and delivery workflows.
- Advocate for design-first thinking, TDD practices, and automated quality validation.
Promote Cost-Effective AI Usage
- Guide teams on effective context management, prompt engineering strategies, and responsible token consumption.
- Help teams balance productivity gains with platform efficiency and governance requirements.
Required Qualifications
Technical Leadership
- 15+ years of software engineering, architecture, or SDLC leadership experience.
- Proven success influencing senior engineers, architects, and technical leadership teams.
- Strong understanding of enterprise software development practices and engineering transformation initiatives.
AI-Native Development Expertise
- Demonstrated hands-on experience with Claude Code and AI-assisted software development workflows.
- Experience implementing AI solutions across software delivery lifecycles.
- Ability to evaluate and improve AI-generated output through structured review, validation, and testing practices.
Full Stack Engineering Background
Strong experience with:
- Java
- Spring Boot
- REST/Web APIs
- Microservices Architecture
- Modern relational and NoSQL databases
- React or other modern SPA frameworks
Coaching & Communication
- Exceptional presentation, mentoring, and facilitation skills.
- Ability to communicate effectively with executive, technical, and non-technical audiences.
- Experience building training programs, mentoring developers, or leading technical enablement initiatives.
Organizational Change Management
- Experience leading large-scale technology adoption or transformation programs.
- Ability to support cultural change and drive adoption across engineering communities.
- Strong emotional intelligence and stakeholder management capabilities.
Quality & Engineering Excellence
- Strong advocate of Test-Driven Development (TDD), automated testing, and quality-first engineering practices.
- Ability to teach developers how to validate, refine, and productionize AI-generated solutions.
Enterprise Environment Experience
- Experience operating within complex enterprise environments with security, governance, compliance, and regulatory requirements.
- Strong critical thinking and problem-solving skills with the ability to connect technical execution to business outcomes.
Preferred Qualifications
- Experience with Kubernetes and Docker.
- Cloud experience in AWS, Azure, and/or GCP environments.
- Experience integrating AI workflows into CI/CD pipelines.
- Familiarity with GitHub, GitHub Actions, and modern code quality platforms.
- Experience developing AI guardrails, custom skills, MCP (Model Context Protocol) servers, or internal AI capabilities.
- Previous training, coaching, developer advocacy, or technical enablement experience strongly preferred.
Education & Experience
Experience
- 10+ years of Software Development Lifecycle (SDLC), Architecture, or Engineering Leadership experience
- 2+ years of AI-native development experience
- Bachelor's degree in Computer Science, Engineering, Information Technology, or related field preferred
- Advanced degrees and relevant technical certifications are a plus
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