Senior Scrum Master / Project Manager – Insurance

Job Description

Senior Scrum Master / Project Manager – Insurance / Telematics

We are seeking a Senior Scrum Master / Project Manager with strong insurance industry experience to support complex, cross-functional Telematics technology initiatives. The ideal candidate will have experience managing initiatives across multiple Agile teams, driving portfolio-level planning, resolving dependencies and blockers, and partnering with Engineering, Product, Business, and technology leadership.

This is not a team-only Scrum Master role. Candidates should demonstrate strong program/initiative-level project management experience across multiple teams and technology domains.

Key Responsibilities:

• Lead planning, coordination, execution, and delivery of complex cross-functional technology initiatives.
• Manage initiative plans, milestones, RAID items, risks, dependencies, blockers, and delivery timelines.
• Facilitate portfolio-level planning, roadmap alignment, dependency management, and stakeholder communication.
• Partner with Engineering Managers, Product Owners, Business Partners, Scrum Masters, and technical teams.
• Drive resolution of cross-team dependencies, risks, and blockers.
• Use Agile/Lean-Agile practices and delivery metrics to improve predictability, transparency, flow, and execution.
• Support Jira standardization, configuration, dashboards, reporting, workflows, and delivery data quality.
• Track large-scale initiatives, dependencies, risks, and delivery metrics across complex technology portfolios.
• Translate complex technical work into clear plans, milestones, status reporting, and executive communications.
• Coach teams and stakeholders on effective planning, execution, continuous improvement, and accountability.
• Support change management and ensure consistent communication and follow-through.

Required Qualifications:

• Bachelor''s degree in Business, Computer Science, Humanities, or a related field.
• 5+ years of relevant experience.
• Previous experience working in the insurance industry is required.
• Experience working across multiple Agile teams and different delivery environments.
• Strong program/project/initiative management experience across multiple teams or technology domains.
• Strong knowledge of business functions, operations, strategies, and objectives.
• Extensive experience with Jira configuration, dashboards, reporting, workflows, and delivery metrics.
• Proven experience managing risks, dependencies, blockers, RAID items, milestones, and cross-team coordination.
• Experience with software engineering delivery, technical planning, release coordination, and delivery risks.
• Strong communication and stakeholder management skills.

Preferred Qualifications:

• Lean-Agile certifications or advanced training such as PSM II, ICP-ATF, or ICP-ACC.
• Telematics industry/product experience.
• Knowledge of Telematics products, data flows, fleet technology, Accident Assistance, or related insurance technology.
• Experience with large-scale technology portfolios and cross-domain initiatives.
• Strong technical understanding of software development and engineering processes.