Location: - This will be a hybrid role, and candidates must be local to Chicago. Our hybrid approach has changed and requires employees and contractors to be in the office twice a week with the remaining days WFH. So, the candidate will need to be able to come to the Chicago office on those in-office days, as the majority of the team is based in the Chicago office
Essential Duties & 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, 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 client' 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.
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Skills, Knowledge & Abilities - 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
Jira Align Proficiency - 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.
AI - 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 adoption of AI-driven practices, including ethical considerations, tool onboarding, and continuous learning.
From a candidate standpoint, these are the specific background items we are a looking for - - Experience working on delivering a legal project
- This means the complete focus the project was legal specific
- This does not mean working with legal or compliance to verify a work item
- Ideally, the candidate has P&C Insurance experience
- Next best is insurance experience, but must be recent
- Experience with Claims is a plus
- Experience using AI in the work
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Education & Experience - Scrum Master Certification (CSM) preferred.
- Bachelor’s degree in computer science, Information Technology, or related discipline; or equivalent work experience.
- Typically, a minimum of four 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.
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