Scrum Master

Must-Haves:

• 10+ years of Agile delivery experience in complex enterprise environments
• Proven Scrum Master expertise (facilitation, coaching, eliminating anti-patterns—not just running ceremonies)
• Scaled Agile Framework (SAFe) / ART experience including PI Planning readiness and execution
• Strong experience managing dependencies, risks, and impediment resolution
• Hands-on experience with Jira, Jira Align, and Jira Software Plans (Advanced Roadmaps)
• Demonstrated experience ensuring data hygiene and reporting accuracy in Jira tools
• Experience operating within Enterprise Change Management / governance environments
• Ability to drive PI Planning readiness (backlog quality, dependencies, capacity planning)
• Strong partnership experience with Product Owner/Product Manager
• Experience using metrics (WIP, cycle time, throughput, defects, etc.) to improve delivery
• Proven ability to maintain stakeholder transparency with executive-level updates
• Minimum 1 year experience using AI tools (Copilot Chat preferred)
• Experience decomposing work into epics/stories using structured approaches (e.g., story mapping, story splitting)

Plusses:

• Experience supporting Technology Infrastructure teams (Database, Middleware, Messaging)
• Hands-on use of Copilot Chat prompt libraries for backlog refinement and story decomposition
• Strong experience with Jeff Patton-style story mapping techniques
• Experience improving team maturity and agile coaching at scale
• Background in platform lifecycle upgrades, resiliency, and operational improvements
• Advanced knowledge of dependency mapping across ARTs
• Strong facilitation skills for decision-driven workshops vs. status meetings

Job Description:

Insight Global is seeking a Scrum Master to support a leading enterprise financial services client within their Technology Infrastructure organization. This individual will guide an Agile team operating within a Scaled Agile (ART) framework, focusing on delivering high-impact initiatives across database, middleware, and messaging platforms.

The Scrum Master will play a critical role in PI Planning readiness and execution, ensuring backlog quality, dependency alignment, and delivery predictability. They will act as a servant leader and coach, driving continuous improvement by leveraging metrics, Agile best practices, and modern tooling such as Jira, Advanced Roadmaps, and AI-enabled Copilot Chat.

This role requires a highly proactive leader who can manage risk, remove impediments, maintain strong stakeholder communication, and elevate team performance within a complex, governance-heavy environment. It offers strong visibility, cross-functional collaboration, and the opportunity to directly influence delivery excellence across enterprise technology platforms.

Day-to-Day:

• Facilitate Scrum ceremonies (Sprint Planning, Daily Standups, Refinement, Reviews, Retrospectives)
• Drive PI Planning preparation and execution , ensuring readiness of backlog, dependencies, and risks
• Monitor and communicate delivery progress, risks, and dependencies via Jira/Jira Align
• Manage and remove impediments; escalate when necessary
• Partner closely with Product Owner to maintain healthy, prioritized backlog
• Use Advanced Roadmaps (Jira Plans) to validate capacity, sequencing, and dependencies
• Maintain Plans hygiene (resolve warnings, fix estimation gaps, correct dependencies)
• Track and improve team performance using delivery metrics (flow, predictability, quality)
• Coach team on Agile best practices, collaboration, and continuous improvement
• Ensure compliance with enterprise governance and change management policies
• Support release readiness and operational handoffs
• Leverage Copilot Chat to accelerate backlog decomposition and planning