Scrum Master

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

We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment regardless of their race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or recruiting process, please send a request to View email address on click.appcast.io learn more about how we collect, keep, and process your private information, please review Insight Global's Workforce Privacy Policy:


Required Skills & Experience
• 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)


Nice to Have Skills & Experience
• 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


Benefit packages for this role will start on the 1st day of employment and include medical, dental, and vision insurance, as well as HSA, FSA, and DCFSA account options, and 401k retirement account access with employer matching. Employees in this role are also entitled to paid sick leave and/or other paid time off as provided by applicable law.