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Portfolio Agile Coach III

Chicago, IL, US • Posted 16 hours ago • Updated 5 hours ago

Full Time

On-site

Fitment

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Job Details

Skills

Agile Coaching
Insurance
Organizational Development
Orchestration
Educate
Collaboration
Knowledge Sharing
User Stories
Management
Prompt Engineering
Productivity
Software Engineering
IT Management
Enterprise Software
Testing
Java
Spring Framework
Microservices
NoSQL
Database
React.js
SPA
Communication
Presentations
Facilitation
Mentorship
Organizational Change Management
Stakeholder Management
Test-driven Development
Automated Testing
Information Security Governance
Regulatory Compliance
Critical Thinking
Conflict Resolution
Problem Solving
Kubernetes
Docker
Cloud Computing
Amazon Web Services
Microsoft Azure
Google Cloud
Google Cloud Platform
Workflow
Continuous Integration
Continuous Delivery
GitHub
Microsoft Certified Professional
Servers
Training
Coaching
Software Development
Software Development Methodology
Leadership
Artificial Intelligence
Computer Science
Information Technology

Agile Coaching
Insurance
Organizational Development
Orchestration
Educate
Collaboration
Knowledge Sharing
User Stories
Management
Prompt Engineering
Productivity
Software Engineering
IT Management
Enterprise Software
Testing
Java
Spring Framework
Microservices
NoSQL
Database
React.js
SPA
Communication
Presentations
Facilitation
Mentorship
Organizational Change Management
Stakeholder Management
Test-driven Development
Automated Testing
Information Security Governance
Regulatory Compliance
Critical Thinking
Conflict Resolution
Problem Solving
Kubernetes
Docker
Cloud Computing
Amazon Web Services
Microsoft Azure
Google Cloud
Google Cloud Platform
Workflow
Continuous Integration
Continuous Delivery
GitHub
Microsoft Certified Professional
Servers
Training
Coaching
Software Development
Software Development Methodology
Leadership
Artificial Intelligence
Computer Science
Information Technology

Summary

Location: Chicago, Illinois
Type: Contract
Job #107186

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 Google Cloud Platform 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

#LI-DO1

Employers have access to artificial intelligence language tools (“AI”) that help generate and enhance job descriptions and AI may have been used to create this description. The position description has been reviewed for accuracy and Dice believes it to correctly reflect the job opportunity.

Dice Id: 10111081
Position Id: 8084a3b7e3eeda35349b20e3508ed8be
Posted 16 hours ago

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