Scrum Master

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

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) - 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

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.