Senior Scrum Master (Contract)

About the role

• 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
• Help us insure it

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 escalate 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 Agile/Scrum experience; Scrum Master or Product Owner certification preferred. PMP certification a plus.
• Advanced experience with Jira and Confluence and proficiency with Microsoft Office tools.
• Strong leadership presence with excellent communication, facilitation, relationship-building, negotiation, and organizational skills.
• Strong technical acumen and working knowledge of software development and technology delivery. While not expected to have the same depth of expertise as an engineer, this individual must be technically proficient enough to understand proposed solutions, ask informed questions, challenge assumptions and estimates when appropriate, identify potential risks and dependencies, facilitate productive discussions with Engineering and other technical teams, and effectively bridge communication between business and technology teams.
• Strong critical-thinking, problem-solving, risk-management, and issue-resolution skills.
• Ability to identify ambiguity, ask the right questions, drive clarity, and facilitate timely decisions.
• Highly proactive, organized, and comfortable operating with a sense of urgency while maintaining high-quality delivery.
• Insurance industry experience preferred.

Physical Demands

While performing the duties of this job, the employee is occasionally required to stand; walk; sit; use hands to finger, handle, or feel objects, tools or controls; reach with hands and arms; balance; stoop, kneel, crouch or crawl; talk or hear; taste or smell. The employee must occasionally lift and/or move up to 5 pounds. Specific vision abilities required by the job include close vision, distance vision, color vision, peripheral vision, depth perception, and the ability to adjust focus.

Work Environment

• While performing the duties of this job, the employee is exposed to weather conditions prevalent at the time.
• The noise level in the work environment is usually moderate.

Pay and benefits

The pay range for this position is $55 - $58 hourly which includes geographic adjustments, where applicable. The pay range is the range THMCC, in good faith, believes is the range of compensation for this role at the time of this posting. The hired applicant will be offered pay within the entire range based on the candidate's geographic location, qualifications, work experience, education, and/or skill level.

After making a conditional offer and running a background check, if the Company is concerned about a conviction that is directly related to the job, you will be given the chance to explain the circumstances surrounding the conviction or challenge the accuracy of the background report.

Applying our Mind Over Risk philosophy to writing insurance allows our customers to take on opportunity with confidence. That philosophy defines our way of thinking, unites us as a team, and differentiates us from our competitors. We are much more than just an insurance company; we are a good company.