Sr. Scrum Master

We’re determined to make a difference and are proud to be an insurance company that goes well beyond coverages and policies. Working here means having every opportunity to achieve your goals - and to help others accomplish theirs, too. Join our team as we help shape the future.

The Hartford is seeking a Sr. Scrum Master to support the End-to-End (E2E) Operating Model Pillar within Strategic Workforce Transformation (SWT). This role will help a cross-functional team deliver an integrated operating model that connects strategy, execution, and measurable outcomes. As facilitator, delivery partner, and Agile practitioner, the Scrum Master will strengthen transparency, accountability, dependency management, and continuous improvement while partnering with pillar and workstream leads, Product Owners, business and technology stakeholders, and other SWT pillars.

• Facilitates planning, team coordination, backlog refinement, reviews, retrospectives, and other working sessions needed to advance E2E Operating Model outcomes.
• Partners with pillar and workstream leads to translate strategic objectives into a prioritized, outcome-based backlog with clear owners, milestones, and acceptance criteria.
• Establishes a consistent delivery cadence and provides visibility into progress, decisions, risks, issues, dependencies, and impediments.
• Coordinates dependencies and handoffs across SWT pillars, business and technology partners, and related transformation efforts.
• Facilitates alignment on the future-state operating model, including roles, decision rights, governance, workflows, measures, and enabling capabilities.
• Drives action-item follow-through and escalates issues that could affect scope, sequencing, readiness, or delivery.
• Uses visual management and delivery tools to maintain an integrated view of priorities, milestones, dependencies, and outcomes.
• Supports roadmap, milestone, decision, pilot, and implementation-readiness planning.
• Enables timely decisions by bringing together the right stakeholders, data, and options and documenting outcomes and implications.
• Promotes transparency, trust, shared accountability, experimentation, and continuous improvement.
• Delivers concise leadership updates on progress, outcomes, risks, decisions, and support needs.
• Supports adoption through stakeholder engagement, change readiness, communications, and transition planning.

This role will have a Hybrid work schedule, with the expectation of working in an office (Hartford, CT, Charlotte, NC or Columbus, OH) 3 days a week (Tuesday through Thursday).

• 5+ years of experience as a Scrum Master, Agile delivery lead, project manager, or transformation practitioner supporting complex, cross-functional initiatives.
• Working knowledge of Scrum, Kanban, Lean, ART, and scaled delivery practices, with the judgment to tailor methods to a transformation team.
• Demonstrated ability to facilitate senior, cross-functional stakeholders; navigate ambiguity; and move teams from discussion to decisions and action.
• Experience managing integrated backlogs, roadmaps, milestones, risks, issues, dependencies, and actions across multiple work streams.
• Strong written, verbal, and visual communication skills, including the ability to synthesize complex information for leadership audiences.
• Strong collaboration, conflict-resolution, and influencing skills, with the ability to build alignment without formal authority.
• Analytical and systems-thinking skills, with the ability to use qualitative and quantitative insights to identify constraints and improve delivery.
• Scrum Master certification, such as CSM or PSM I.

• Experience supporting enterprise transformation, operating model…