Senior Scrum Master (Contract)

Tokio Marine HCC - Cyber & Professional Lines Group; United States; Hybrid; USD 96,000 - 152,000; Full time

Job summary

Tokio Marine HCC - Cyber & Professional Lines Group in Encino, CA seeks a Senior Scrum Master for a 1+ year contract. This role leads cross-functional Scrum teams, ensuring accountability and rapid delivery in a hybrid on-site/remote setup.

You will facilitate agile ceremonies, partner with Product Management, and coordinate release readiness across multiple functions to realize business value.

Qualifications

• Bachelor’s degree and 5+ years of project/program management or agile delivery leadership experience.
• Demonstrated ability to lead complex, cross‑functional initiatives in a fast‑paced environment with multiple competing priorities.
• Strong communication and collaboration skills.

Responsibilities

• Lead cross‑functional Scrum teams, clarifying priorities, ownership, timelines, and delivery accountability.
• Facilitate agile routines including backlog refinement, sprint planning, daily coordination, retrospectives, and release planning.
• Partner with Product Management and business leaders to translate objectives into clear Product Goals and backlogs.
• Manage epics, stories, tasks, milestones, dependencies, risks, and resources in Jira.
• Coordinate release readiness and deployment activities across multiple stakeholders to minimize handoffs.

Skills

Project management

Agile delivery leadership

Cross-functional leadership

Jira

Education

Bachelor’s degree

Tools

Jira

Job description

Job Title: Senior Scrum Master (Contract) Location: Encino, CA (Hybrid onsite 1 day a week or remote) Reports to: Senior Project Manager Employment Type: Contract Contract Length: 1+ years

Tokio Marine HCC is a global industry-leading specialty insurance group, backed by the strength and stability of the Tokio Marine Group. Offering over 100 classes of specialty insurance, we empower clients to pursue opportunities confidently through our “Mind Over Risk” philosophy. More than an insurance company, we are an organization built on innovation, unity, and trust.

At our core, we are Always Advancing, driven by innovation and an entrepreneurial spirit that keeps us moving forward. Our people are Experts in Tomorrow, using curiosity and smart working to anticipate what’s next. With a culture rooted in Reaching Out, we foster genuine collaboration and support, ensuring every individual has the opportunity to succeed and make a difference.

Role Overview

The Senior Scrum Master plays a key role in CPLG's evolution to become a faster, more intelligent, and scalable organization. This role leads and coordinates highly visible, cross‑functional Scrum teams across Product Management, Engineering, QA, Infrastructure, Underwriting, Operations, Business Intelligence, and other business functions to deliver measurable business outcomes.

The Senior Scrum Master is responsible for creating the structure, transparency, and accountability needed to move initiatives forward quickly while proactively identifying dependencies, risks, and barriers to execution. This individual facilitates agile delivery, drives cross-functional collaboration and decision‑making, and ensures teams remain focused on priorities from planning through implementation and realization of business results. The Scrum Master is accountable for the Scrum Team's effectiveness, enabling the team to continuously improve its practices within the Scrum framework and coaching team members toward greater self‑management and effectiveness.

Essential Duties & Responsibilities

• Lead and support highly visible, cross‑functional Scrum teams, creating clarity around priorities, ownership, timelines, and accountability for delivery while coaching teams toward greater self‑management.
• Facilitate agile routines including backlog refinement, sprint planning, daily coordination, retrospectives, and release planning.
• Partner with Product Management and business leaders, helping teams identify and apply effective techniques for translating business objectives into clear Product Goals, well‑managed backlogs, actionable initiatives, requirements, and measurable outcomes.
• Manage epics, stories, tasks, milestones, dependencies, risks, and resources through Jira and other project management tools.
• Coordinate activities across Product, Engineering, QA, Infrastructure, Underwriting, Operations, BI, and other stakeholders to minimize handoffs and remove delivery barriers.
• Engage confidently with Engineering and technical teams to understand proposed solutions, ask probing questions, challenge assumptions and estimates when appropriate, and help teams identify practical options for delivering business value efficiently.
• Drive teams toward timely decisions and proactively escalte issues when additional authority, resources, or organizational alignment is required.
• Establish clear plans and communication across multiple concurrent workstreams, ensuring stakeholders understand progress, risks, decisions, and next steps.
• Coordinate release readiness and deployment activities, including testing, implementation planning, dependencies, and post‑launch follow‑through.
• Ensure teams maintain ownership after implementation to confirm intended business outcomes are achieved and identify opportunities for continued improvement.
• Use retrospectives, lessons learned, metrics, root‑cause analysis, and ongoing coaching to help Scrum Teams improve their practices, effectiveness, self‑management, and delivery processes.
• Prepare and facilitate effective meetings with clear objectives, decisions, owners, and next steps.
• Promote a collaborative, accountable, and positive team culture that encourages transparency, active problem‑solving, and continuous improvement.
• Demonstrates the ability to challenge conventional thinking and encourage teams to look beyond established ways of working, identifying creative and practical solutions that accelerate delivery and maximize business value.

Required Knowledge, Skills & Abilities

• Bachelor’s degree and 5+ years of project/program management or agile delivery leadership experience.
• Demonstrated ability to lead complex, cross‑functional initiatives in a fast‑paced environment with multiple competing priorities.
• Strong