Senior Agile Scrum Master – AI-Driven Delivery & Automation

Our customer is a large United States insurance company that is backed by more than 100 years of experience and provides insurance products and services for businesses and professionals in the United States., Canada and Europe. Headquartered in Chicago, IL, they have more than 20 US locations.

We are seeking a contract Senior Agile Scrum Master – AI-Driven Delivery & Automation to support our Customer's business needs. This role is hybrid (3 days remote and 2 days onsite) in Chicago, IL.

Responsibilities:

• Performs a combination of duties in accordance with departmental guidelines:
• 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, 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 the 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 a 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.

Skills and Qualifications:

• Bachelor’s degree in computer science, Information Technology, or related discipline; or equivalent work experience.
• Scrum Master Certification (CSM) preferred.
• A minimum of 4 years of related work experience, such as project delivery background in an enterprise IT environment, with experience using Agile delivery methods. Previous project management experience preferred. Applicable certifications are preferred.
• Required Skills – AI & Tooling Awareness
• 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 the adoption of AI-driven practices, including ethical considerations, tool onboarding, and continuous learning.
• Hands-on experience using Jira Align to connect strategy to execution, manage program-level backlogs, and visualize dependencies across Agile Release Trains (ARTs). Ability to configure and interpret dashboards, OKRs, and lean metrics.
• Prior experience with Agile Scrum methodology in a Scrum Master role.
• Solid experience acting as a servant-leader with strong coaching and mentoring skills; ability to get work done without assigning/dictating tasks.
• Experience in teams delivering modern software for enterprises using Agile methodologies.
• Strong communication, facilitation, and interpersonal skills, and the ability to work effectively with peers and team members.
• Excellent personal organizational skills and prior experience using Agile management tools such as Jira.
• Proven track record of experience applying App. Dev. best practices on an initiative (e.g., automation, CI/CD pipelines) and consistently adopts these best practices as appropriate

We offer a competitive salary range for this position. Most candidates who join our team are hired at the median of this range, ensuring fair and equitable compensation based on experience and qualifications.

Contractor benefits are available through our 3rd Party Employer of Record (Available upon completion of waiting period for eligible engagements)

Benefits include: Medical, Dental, Vision, 401k.

An Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, or protected veteran status and will not be discriminated against on the basis of disability.