Scrum Master

About the role

Seeking a Scrum Master that has managed large initiatives. This is a contract position based in Chicago, Illinois.

Responsibilities

• Serves, leads, coaches, and supports multiple Agile Scrum Teams on complex initiatives, with teams consisting of internal & external (onshore and offshore) as well as business and technical resources in the delivery of IT and business products and solutions.
• Responsible for product delivery.
• Facilitates Scrum ceremonies and agile practices (such as daily standups, sprint review meetings, retrospective meetings, cross-team coordination, and etc.), alongside the product owner, ensuring that Scrum Teams adhere to the Scrum values of courage, focus, commitment, respect and openness in delivering IT solutions.
• Identifies and resolves delivery impediments to optimize delivery flow.
• Appropriately leads resolution of complex impediments and escalates impediments that cannot be resolved to senior leadership.
• Manages risks and issues and acts to ensure they do not recur.
• Fosters an environment of continuous improvement / learning and drives substantial improvement to the team (e.g., via the retrospective process).
• Guides team members in achieving maturity in Agile principles and Scrum practices, developing a proven track record of driving consistent velocity and velocity increases on mature teams.
• Proactively monitors and assesses team health and project needs.
• Serves as recognized Agile subject matter expert, thought leader, and mentor with extensive knowledge of Agile processes, tools, best practices, and standards.
• Provides guidance to more junior Scrum Masters on Agile Reviews and provides feedback on potential new tools / processes in the Agile space and is a visible champion for adopting them once ratified.
• Contributes to maturing Agile at CNA through proactively bringing suggestions to COE / COPs.
• Creates a strong team environment, with high team morale and cohesion.
• Supports the Product Owner in managing backlog and guides the Product Owner / Scrum Team in prioritization, including maintaining relevant metrics.
• Maintains strong relationships within their Agile team, particularly with the Product Owner.
• Coordinates interactions within and outside the Scrum Team.
• Builds a trusting and safe environment within the team, Product Owners, and other stakeholders.
• Facilitates and manages conflict resolution within the team and key stakeholders; escalates more serious conflicts to leadership.
• Promotes practices that ensure delivery of quality products, ensuring that transparency is maintained around delivery progress, quality and schedule.
• May perform additional duties as assigned.

Qualifications

• Applied AI Literacy: Demonstrated understanding of how Artificial Intelligence (AI) and Machine Learning (ML) concepts intersect with Agile delivery—e.g., predictive analytics for sprint planning, intelligent backlog grooming, or automation of reporting.
• Tool Familiarity: Working knowledge of AI-enhanced platforms such as Jira Automation, Rovo, GitHub Copilot, Lucid AI, or Microsoft Copilot, with the ability to leverage these tools to streamline workflows, facilitate retrospectives, and enhance team productivity.
• Data-Informed Decision Making: Ability to interpret AI-generated insights (e.g., velocity trends, risk flags, sentiment analysis) and translate them into actionable guidance for teams.
• Change Enablement: Experience coaching teams through adoption of AI-driven practices, including ethical considerations, tool onboarding, and continuous learning.

Pay

$65 - 75 per hour

Schedule

9am to 5pm

Education

Bachelors