Sr. Scrum Master - Liberty Mutual Global Risk Solutions, Claims Tech

Description
At Liberty, you'll thrive in a hybrid setting that fosters in-person collaboration, innovation and growth. This approach optimizes both remote and in-person interactions, enabling you to connect and ideate with your team and deepen valuable relationships across the company, while still enjoying the flexibility of remote work for focused tasks and projects. This position follows a hybrid work model (2 days onsite) and is open to candidates located in Portsmouth, NH; Boston, MA; Plano, TX; Indianapolis, IN; and Columbus, OH.

Evergreen Workers' Compensation Transformation Program (Flagship Initiative)

We deliver our customers peace of mind every day by helping them protect what they value most. Our passion for placing the customer at the center of everything we do is driving a transformational shift at Liberty Mutual. Operating as a tech start-up within a Fortune 100 company, we are leading a digital disruption that will redefine how people experience insurance.

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Evergreen Vision

We will be trusted advisors in Workers Compensation by deploying our deep expertise to manage claims accurately and efficiently, producing the best outcomes for our customers and injured workers, while also providing best in class insights to improve risk management decision making.

Modern & Scalable Platform for WC

Replacement of existing claims core platform, with a new cloud platform for claims ops. that enables holistic claims handling along with modern capabilities that are market relevant, scalable, and future ready

Business Transformation

Reimagining of key business processes and functions to drive efficient processing and adherence to the best-in-class ways of handing claims

Technology Modernization Acceleration

Retirement of existing claims platform and modernization of the surrounding ecosystem with flexible, composable architecture with modular integrations

Extensible Solution Ecosystem

Improve overall technology landscape by building & enhancing shared scalable component solutions that can be leveraged beyond Evergreen
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The Opportunity

Join Evergreen - Liberty Mutual's multi-year, business-led, tech-enabled transformation of our Workers' Compensation line. Reporting to the Senior Director of Technology, you will serve as the Sr. Scrum Master / RTE-like leader driving execution across 10+ agile teams. You will own program-level metrics and Jira data, building the dashboards, forecasts, and reports that give Program Execution Leads clear, timely visibility into progress, risks, and feasible delivery options, and you'll coordinate cross-team cadence, dependency management, and issue resolution to keep delivery on track.

• Own program metrics and reporting for Evergreen - define, maintain, and continuously improve the KPI set, dashboards, and data quality that measure team execution across 10+ agile teams.
• Provide timely, actionable visibility to Program Execution Leads and senior stakeholders on team progress, delivery forecasts, risks, and trade-off options; publish regular program health reports and an up-to-date risk & mitigation register.
• Translate Jira data into clear insights: build and maintain Epic/Story hygiene, advanced JQL queries, automated dashboards, custom reports, and scorecards (velocity, predictability, lead time/cycle time, throughput, WIP, blocked time, defect/escape rates, etc.).
• Drive forecasting and capacity planning using Jira metrics and historical trends; surface feasible delivery options and recommend pragmatic adjustments to scope, staffing, or schedule.
• Pair up with the RTE, and collaborate with the Program Managers to coordinate program-level cadence: lead Scrum-of-Scrums, PI/Program planning sessions, dependency reviews, Inspect & Adapt, and other cross-team ceremonies that sustain alignment and delivery momentum.
• Proactively identify bottlenecks and impediments across teams; remove or escalate blockers, coordinate cross-team resolution, and track closure to ensure timely delivery.
• Partner closely with RTE, Product, Engineering, Architecture, and PMO to align priorities, manage dependencies, and ensure release readiness and deployment coordination.
• Implement and enforce ticket hygiene, workflow standards, and governance in Jira to ensure traceability, consistent estimations, and reliable data for decision-making.
• Design and operationalize automated reporting and alerts (via Jira, Confluence, BI tools, or integrations) to reduce manual status work and accelerate issue detection.
• Coach and mentor Scrum Masters, Product Owners, and delivery leads on agile best practices, data-driven decision making, and using Jira effectively to improve predictability and throughput.
• Lead continuous improvement initiatives informed by metrics and team feedback - run experiments, measure impact, and socialize outcomes to raise delivery maturity across the program.
• Ensure metrics and reporting are auditable and defensible - validate data sources, resolve discrepancies, and maintain documentation of measurement definitions and thresholds.
• Serve as a servant leader and trusted advisor: facilitate tough conversations, surface trade-offs, and present recommended options and consequences to Program Execution Leads and stakeholders to enable timely decisions.
• Contribute to tooling and process improvements (automations, Advanced Roadmaps/Jira Align, plugins, integrations) that scale program reporting and reduce overhead.

• 7+ years delivering software using Agile methods, with 3+ years as a Scrum Master / RTE-like role supporting multi-team programs (10+ teams).
• Proven experience coaching and operating at scale (SAFe, LeSS, Scrum@Scale or equivalent) - running PI/Program-level planning, dependency management, Inspect & Adapt, and cross-team facilitation.
• Deep, hands-on Atlassian Jira expertise (Admin or power-user): epic/story management, board and workflow design, advanced JQL, automation, custom fields, Advanced Roadmaps / Jira Align, and ticket hygiene best practices.
• Demonstrated ability to design and implement program-wide execution metrics and dashboards (velocity, predictability, lead time/cycle time, throughput, WIP, blocked work), using Jira and BI/analytics tools (e.g., Power BI, Tableau, Confluence).
• Data-driven mindset with experience using Jira data to forecast delivery, identify bottlenecks, measure outcomes, and drive continuous improvement.
• Strong facilitation, coaching, and servant-leader skills - skilled at removing impediments, escalating appropriately, and influencing without direct authority across engineering, product, and leadership.
• Solid understanding of modern software delivery (CI/CD, DevSecOps practices) and enough technical fluency to partner effectively with engineering teams.
• Excellent written and verbal communication skills and experience producing concise program status reporting for senior stakeholders.
• Relevant certifications preferred: CSM/PSM, SAFe SM/SPC or RTE, and Atlassian Jira Administrator or Jira Project Administrator.
• Bachelor's degree in computer science, Engineering, Business, or equivalent practical experience.

• A life-long learner who stays on top of technology trends and encourages experimentation.
• A pragmatic, inclusive leader who builds psychological safety, values diverse perspectives, and empowers teams to take smart risks.
• A go-getter who owns outcomes, raises the bar for reliability, security, scalability, and cost efficiency-and inspires others to do the same.
• A collaborator who drives consensus across business, operations, and technology stakeholders.

• California
• Los Angeles Incorporated
• Los Angeles Unincorporated
• Philadelphia
• San Francisco