Agile Coach

The Judge Group; Chicago (IL); On-site; USD 117,000 - 131,000; Full time

Job summary

The Judge Group seeks a Senior Agile Transformation Coach to lead enterprise-wide Agile modernization with a strong AI enablement focus. The role partners with leadership, product teams, and technology groups to establish scalable operating models, optimize value streams, and accelerate product delivery.

You will coach executives and delivery teams on Lean-Agile principles, drive AI-enabled workflows, and design governance, playbooks, and maturity models for sustained change across the

Qualifications

• 10+ years of Agile, Product and transformation leadership in large enterprises.
• Deep expertise with Lean-Agile methodologies and scalable frameworks.
• Proven experience designing portfolio-level Agile transformations and operating models.
• Experience creating playbooks, coaching frameworks, maturity models and exec communications.
• Strong executive presence with facilitation and stakeholder management.
• Pay rate could be 85-95/hr
• Experience with AI assistants, AI agents or AI-enabled workflows.
• Proven ability to drive cultural change and organizational effectiveness at scale.

Responsibilities

• Lead enterprise-wide Agile modernization initiatives across programs and business units.
• Assess Agile maturity and develop transformation roadmaps with measurable outcomes.
• Coach executives, product leaders, PO and delivery teams on Lean-Agile and product thinking.
• Design and implement Agile frameworks, governance, playbooks and maturity assessments.
• Drive adoption of AI-enabled coaching, tools, and workflows to boost planning and reporting.
• Partner with stakeholders to identify AI opportunities to improve agility and delivery.
• Establish and track transformation metrics including flow and team health.

Skills

Lean-Agile methodologies

SAFe/LeSS/Scale frameworks

Executive coaching

Portfolio transformation

AI in transformation

Change management

Job description

We are seeking a Senior Agile Transformation Coach to lead enterprise-wide Agile modernization initiatives, with a strong focus on AI enablement, Lean-Agile adoption, and large-scale organizational transformation. This role will partner with leadership, product teams, and technology organizations to establish scalable operating models, optimize value streams, accelerate product delivery, and embed AI-powered ways of working across the enterprise.

Key Responsibilities

• Lead large-scale Agile and product operating model transformations across programs, portfolios, and business units.
• Assess organizational Agile maturity and develop transformation roadmaps that drive measurable business outcomes.
• Coach executives, product leaders, Product Owners, and delivery teams on Lean-Agile principles, product thinking, value stream management, and continuous improvement.
• Design and implement Agile frameworks, governance models, playbooks, maturity assessments, and enablement content.
• Drive adoption of AI-enabled coaching, AI assistants, agents, and productivity tools to enhance planning, knowledge management, reporting, and team effectiveness.
• Partner with stakeholders to identify opportunities where AI can improve organizational agility, delivery performance, and decision-making.
• Establish and track transformation metrics, including flow, predictability, team health, and maturity measures.

Required Qualifications

• 10+ years of experience leading Agile, Product, and Organizational Transformation initiatives within large enterprise environments, preferably financial services.
• Deep expertise with Lean-Agile methodologies (SAFe, LeSS, Scrum@Scale, DAD, Spotify, or similar frameworks).
• Proven experience designing and executing portfolio-level Agile transformations, value stream organizations, and operating models.
• Experience creating Agile playbooks, coaching frameworks, maturity models, training materials, and executive communications.
• Strong executive presence with exceptional facilitation, influence, and stakeholder management skills.
• Pay rate could be 85-95/hr
• Experience with AI assistants, AI agents, Generative AI solutions, or AI-enabled workflow automation.
• Demonstrated ability to drive cultural change, organizational effectiveness, and continuous improvement at scale.