Sr. Scrum Master

The Hartford•Hartford, CT

1d•$108,800 - $163,200•Hybrid

About The Position

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.

Requirements

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 workstreams.
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.

Nice To Haves

Experience supporting enterprise transformation, operating model design, organizational change, or workforce transformation.
Experience working across business, technology, data, governance, and change-management stakeholders.
Experience with Rally, Jira, Azure DevOps, or comparable Agile delivery and visual-management tools.
Proficiency with Excel, PowerPoint, Microsoft Teams, and collaborative planning tools.
Familiarity with ADKAR or another structured change-management framework.
Advanced Scrum Master, SAFe, Lean, or change-management certification.
Insurance industry experience or knowledge.

Responsibilities

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.