Senior Director, AI Transformation - Enterprise Architecture

Fitch Group • Chicago, IL

4d • $230,000 - $260,000 • Hybrid

About The Position

Fitch Group is currently seeking a Senior Director, AI Transformation – Enterprise Architecture based out of our Chicago office. As a Senior Director of AI Transformation within Enterprise Architecture, you will serve as a catalyst for organizational change—evangelizing AI adoption and leading squads through immersive innovation sprints that fundamentally reshape how teams build and deliver software. You will drive the AI transformation of enterprise architecture itself, building the agents and automation that power every phase of the EA lifecycle, from technology evaluation and ARB review to application and service catalog management. Your mission is to lead adoption of the AI-enhanced Development Lifecycle (AI-DLC), champion a new way of working across the organization, and ensure our team stays ahead of emerging technological shifts through continuous research and rapid adoption of new capabilities.
This role sits within Enterprise Architecture and will require building strong, trusted relationships with engineering squad leaders across Fitch Group, Fitch Ratings, Fitch Solutions, and Fitch Learning. Each organization operates with distinct priorities, workflows, and challenges — success in this role depends on the ability to drive adoption through influence and demonstrable value rather than mandate. You will need to tailor your approach to the nuances of each environment, understanding that what works for one group may need to be adapted for another, and earning buy-in by delivering measurable outcomes that speak to each team's specific context.

Requirements

• Enterprise Architecture Expertise: A strong record of designing and evolving enterprise architectures, with the ability to lead AI-driven transformation of EA practices and tooling.
• AI Agent & LLM Experience: Demonstrated experience building AI agents, working with LLMs, and applying agentic patterns to automate complex workflows and business processes.
• AI-DLC & Development Transformation: Experience leading the adoption of AI-enhanced development practices, including AI-assisted coding, testing, and deployment across engineering organizations.
• Sprint Facilitation & Evangelism: Proven ability to design and facilitate innovation sprints, workshops, or similar immersive engagements that drive technology adoption and cultural change.
• Transformational Leadership: Exceptional ability to inspire and influence without direct authority, communicating transformation vision in compelling terms that motivate teams to embrace new ways of working.
• Research & Technology Scouting: A proactive research orientation with the ability to rapidly evaluate emerging technologies and translate findings into practical adoption strategies for the organization.
• Analytical & Consulting Abilities: Excellent planning, analytical, and consultative skills to manage sprint backlogs, prioritize squad engagements, and drive strategic adoption across diverse stakeholder groups.
• Communication & Storytelling: Ability to articulate transformation narratives that connect AI capabilities to business outcomes, making complex technical concepts accessible to executives, product leaders, and engineering teams alike.
• Cross-Functional Influence: Strong interpersonal skills with the ability to build trust and drive alignment across engineering, product, and business teams toward shared transformation goals.

Nice To Haves

• Proven AI Transformation Track Record: A demonstrated history of leading organization-wide AI transformation initiatives, with measurable improvements in team productivity, adoption rates, and development velocity.
• Innovation Sprint Methodology: Experience designing and scaling structured innovation sprint programs, including backlog management, squad prioritization, and repeatable engagement frameworks.
• EA Automation & Agent Development: Hands-on experience building AI agents for enterprise architecture functions such as technology evaluation, architecture review, and catalog management.
• AI-DLC Implementation: Direct experience implementing AI-enhanced development lifecycles across multiple teams, with demonstrated ability to shift organizational culture toward AI-first practices.
• Transformational Communication: Exceptional ability to frame technical transformation in business terms, with experience presenting to senior leadership and building grassroots support simultaneously.
• Forward-Looking Technology Vision: Deep understanding of the rapidly evolving AI landscape with a proven ability to identify and adopt emerging technologies before they become mainstream, keeping the organization ahead of the curve.
• Culture of Continuous Innovation: A passion for building a culture where experimentation and learning are celebrated, with experience creating feedback loops that accelerate organizational learning and technology adoption.
• Research-Driven Leadership: A structured approach to technology research and scouting, with the ability to distill complex emerging trends into clear, actionable recommendations that help the team prepare for and rapidly adopt future technological changes.

Responsibilities

• Run Immersive Innovation Sprints: Plan, schedule, and execute immersive innovation sprints with squads across the organization in close partnership with the Emerging Technology Group. Manage the sprint backlog, prioritize squad engagements, and deliver hands-on sessions that accelerate AI adoption and agent development.
• Transform Enterprise Architecture with AI: Lead the AI transformation of the Enterprise Architecture function by building agents that automate technology evaluation, streamline ARB submission reviews, and intelligently manage the application and service catalog.
• Drive AI-DLC Adoption: Partner with the Emerging Technology Group to lead the organization-wide adoption of the AI-enhanced Development Lifecycle (AI-DLC), equipping squads with the tools, patterns, and practices to integrate AI into every stage of their software delivery process.
• Evangelize a New Way of Working: Act as a transformational leader who communicates the vision for AI-enabled development in compelling, accessible terms. Build excitement and momentum across squads by demonstrating tangible value and celebrating early wins.
• Build EA Lifecycle Agents: Architect and develop AI agents that support every pillar of the EA lifecycle—Evaluate, Design, Build, Govern, Discover, Evolve, and Communicate—positioning Enterprise Architecture as the intelligent system of record.
• Research & Rapid Capability Adoption: Continuously partner with our Emerging Technology Group to evaluate emerging AI technologies, frameworks, and best practices. Translate research findings into actionable recommendations that enable the team to rapidly adopt new capabilities and stay ahead of industry shifts.
• Bridge Business & Technology: Translate transformation goals into clear, actionable architecture strategies. Communicate the value of AI-driven change in business terms that resonate with stakeholders at every level.
• Foster Cross-Functional Collaboration: Partner with software engineering, product management, emerging technology, and IT operations to align AI transformation initiatives with broader enterprise objectives and drive cohesive adoption.
• Transformational Leadership: Inspire and lead through influence, building a coalition of champions across the organization who amplify the AI transformation message and drive adoption within their own teams

Benefits

• Hybrid Work Environment: 2 to 3 days a week in office required based on your line of business and location
• A Culture of Learning & Mobility: Dedicated trainings, leadership development and mentorship programs designed to ensure that your time at Fitch will be a continuous learning opportunity
• Investing in Your Future: Retirement planning and tuition reimbursement programs that empower you to achieve your short and long-term goals
• Promoting Health & Wellbeing: Comprehensive healthcare offerings that enable physical, mental, financial, social, and occupational wellbeing
• Supportive Parenting Policies: Family-friendly policies, including a generous global parental leave plan, designed to help you balance career and family life effectively
• Inclusive Work Environment: A collaborative workplace where all voices are valued, with Employee Resource Groups that unite and empower our colleagues around the globe
• Dedication to Giving Back: Paid volunteer days, matched funding for donations and ample opportunities to volunteer in your community

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed