Senior Agile Coach

Job Description

Senior Agile Transformation & AI Enablement Lead

Job Type: Contract

Experience: 10+ Years

Industry: Banking / Financial Services

Location: Downtown Chicago, Hybrid role (3 days/week to work, rest from home)

Position Overview

We are seeking a Senior Agile Transformation & AI Enablement Lead to drive enterprise Agile transformation and modernization across a large financial services technology organization.

This role operates at the enterprise, portfolio, and program levels, helping scale Agile practices, product management, and product ownership capabilities across approximately 150 Agile teams.

The ideal candidate brings extensive experience leading large-scale Agile transformations, developing portfolio-level operating models and value streams, and creating practical Agile frameworks and guidance. Experience developing or leveraging AI agents to enhance Agile assessments and organizational effectiveness is highly desirable.

Key Responsibilities

• Lead enterprise and portfolio-level Agile transformation initiatives, influencing technology, business, and operations leadership.
• Establish and scale Agile frameworks, operating models, value streams, and transformation roadmaps.
• Coach product owners, business analysts, architects, and development leaders on product discovery, backlog management, prioritization, and delivery practices.
• Conduct Agile maturity and health assessments, identify improvement opportunities, and develop actionable transformation plans.
• Establish program metrics, maturity models, flow measurements, and delivery predictability indicators.
• Develop enterprise Agile playbooks, coaching frameworks, assessment tools, guidance materials, and thought leadership content.
• Explore and develop AI-enabled solutions and agents to automate Agile assessments, analyze team artifacts, and improve coaching effectiveness.
• Evaluate AI-generated insights and recommendations with appropriate human oversight.

Required Qualifications

• 10+ years of experience in Agile coaching, product management, and organizational transformation within large financial services or enterprise environments.
• Direct experience leading scaled Agile execution across financial services technology portfolios.
• Experience transitioning traditional waterfall project structures into Lean-Agile value streams.
• Strong knowledge of scaled Agile frameworks such as SAFe, LeSS, DAD, Spotify, or View email address on ziprecruiter.com.
• Experience establishing portfolio-level workflows, operating models, and transformation roadmaps.
• Proven ability to develop Agile playbooks, maturity models, coaching frameworks, and enterprise guidance.
• Exceptional written and verbal communication skills, including the ability to influence senior leadership.

Preferred Qualifications

• Experience developing, implementing, or experimenting with AI assistants, AI agents, or generative AI solutions.
• Experience using AI to automate assessments, analyze Agile artifacts, and improve organizational productivity.
• Experience in large, complex, regulated financial institutions.

Mandatory Submission Requirement – Writing Samples

Candidates must submit writing samples along with their initial resume.

Acceptable examples include published articles, blogs, whitepapers, LinkedIn posts, internal Agile guidance, playbooks, or thought leadership materials.