Scrum Master AI-Powered

About Grey Parrot Systems

Grey Parrot Systems (GPARROT) is a women-owned, BEP-certified IT services firm headquartered in Naperville, IL. We partner with mid-market enterprises to deliver AI-first, governance-driven digital transformation. Our team of seasoned CIO/CTO practitioners works side-by-side with clients across retail, logistics, manufacturing, and healthcare — and we're growing.

About the Role

This is not a traditional Scrum Master role. We are looking for someone who has already crossed the line from "aware of AI tools" to "actively using AI tools every single day" — and who can bring other Scrum Masters across that same line. You will use Claude and other AI tools to generate structured, high-quality user stories and acceptance criteria directly from requirements conversations, and you will train and mentor the existing Scrum Master team on how to do the same — building lasting AI fluency and productivity across our delivery practice.

You are a strong Agile practitioner first — you know how to run a great sprint, keep teams unblocked, and drive delivery outcomes. But you are also an AI-first operator who knows how to prompt Claude to generate MCP-aligned user stories, how to use AI to accelerate retrospectives and planning, and how to teach others to do the same without making it feel complicated. If you are a senior Scrum Master who is already working this way — this role was built for you.

Must-Have Skills

• 8+ years of Scrum Master or Agile delivery experience
• Active, daily hands-on use of AI tools — Claude, ChatGPT, GitHub Copilot, or similar — mandatory
• Proven ability to use Claude or similar LLMs to generate structured, high-quality user stories and acceptance criteria from requirements conversations, interview notes, or business context
• Experience writing AI prompts that produce MCP-aligned, developer-ready user stories — structured for AI coding agents and QA automation tools to consume directly
• Strong coaching and mentoring skills — proven ability to train and upskill other Scrum Masters or Agile practitioners on new tools, practices, and workflows
• Deep hands-on Agile / Scrum expertise — sprint planning, backlog grooming, retrospectives, daily standups, and release management
• Experience with Jira — sprint boards, backlog management, velocity tracking, advanced JQL, and reporting
• Strong facilitation, coaching, and stakeholder communication skills
• Certified Scrum Master (CSM), Professional Scrum Master (PSM), or equivalent certification
• Strong written and oral communication skills — comfortable presenting AI-assisted delivery approaches to technical and business stakeholders

What You'll Do

AI-Powered User Story Generation

• Use Claude and other AI tools daily to generate structured, high-quality user stories, acceptance criteria, and definition-of-done from requirements conversations, business briefs, and interview notes
• Design and refine AI prompts that produce MCP-aligned, developer-ready user stories — structured so AI coding agents and QA automation tools can consume and act on them directly
• Work directly with product owners and business stakeholders to capture requirements and immediately translate them into AI-generated, sprint-ready backlog items
• Validate and refine AI-generated user stories — ensuring accuracy, completeness, testability, and alignment with business intent before sprint commitment
• Build a reusable library of AI prompt templates for user story generation, acceptance criteria writing, and definition-of-done creation across GPARROT delivery teams

Scrum Master AI Coaching & Upskilling

• Train, coach, and mentor existing Scrum Masters on how to use Claude and other AI tools effectively and productively in their daily Agile delivery workflows
• Design and deliver practical AI upskilling sessions — hands-on workshops, prompt engineering exercises, and real-sprint AI workflow demonstrations
• Build AI adoption playbooks for Scrum Masters — covering user story generation, retrospective facilitation, sprint planning acceleration, and backlog grooming with AI
• Monitor and measure AI tool adoption and productivity improvements across coached Scrum Masters — adjusting training approaches based on results
• Serve as the GPARROT AI-first Agile practice lead — continuously evaluating new AI tools, prompt patterns, and delivery accelerators and sharing best practices across the team

Core Scrum Master Delivery

• Facilitate all Scrum ceremonies — sprint planning, daily standups, sprint reviews, retrospectives, and backlog grooming — with precision and energy
• Own sprint health — tracking velocity, capacity, burndown, and delivery risks across one or more engineering teams
• Identify, escalate, and remove blockers — technical, organizational, and process-related
• Partner with Product Owners to ensure the backlog is well-defined, prioritized, and sprint-ready
• Track and report on team delivery metrics — velocity, cycle time, sprint completion rate, and quality indicators
• Support the adoption of AI-DLC (AI-Driven Lifecycle) and MCP-based development practices across engineering and QA teams

Tools You'll Use

Claude · ChatGPT · GitHub Copilot · Cursor · Jira · Confluence · Azure DevOps · Miro / FigJam · Microsoft 365 · MCP (Model Context Protocol) · AI Prompt Engineering Frameworks

Nice to Have

• Experience writing MCP-aligned user stories structured for AI coding agents — Claude Code, Cursor, or GitHub Copilot — to generate UI or backend code directly from story context
• Experience with MCP Jira integration — enabling AI agents to read Jira user stories and generate automated test cases
• SAFe Scrum Master (SSM) or SAFe Agilist (SA) certification
• Experience running Scrum at scale — SAFe, LeSS, or Nexus frameworks
• Familiarity with AI-DLC quality engineering practices and MCP Playwright integrations
• Experience in a consulting or IT services firm environment
• Background in prompt engineering — designing reusable prompt templates and AI workflow patterns for delivery teams

Details

• Location: Naperville / Chicago, IL
• Experience: 8+
• Type: Full-Time
• AI Tool Proficiency: Active daily use of Claude and AI tools is mandatory — not optional
• Start: Immediate

Grey Parrot Systems is an Equal Opportunity Employer. As a women-owned, BEP and WBENC-certified firm, diversity and inclusion are core to who we are. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, veteran status, marital status, or any other legally protected characteristic. We strongly encourage applications from candidates of all backgrounds, identities, and experiences — including those from underrepresented groups in technology. Reasonable accommodations are available upon request.

Stay Connected

For more job openings, company updates, and AI industry insights, follow Grey Parrot Systems on LinkedIn.

👉 https://www.linkedin.com/company/gparrot/

We are always looking for talented, driven professionals to join our growing team. Whether this role is the right fit today or not, connect with us and be the first to hear about new opportunities as we expand across Chicago, Detroit, and the Midwest.