Senior IT Scrum Master (Contract)

Job Title: Senior IT Scrum Master (Contract)
Location: Encino, CA (Hybrid onsite 3 days a week)
Reports to: Senior Project Manager
Employment Type: Contract
Contract Length: 1+ years
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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 IT 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 IT 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.
When possible, reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.
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.
When possible, reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.
Tokio Marine HCC is an equal opportunity employer that values diversity and inclusion. We offer competitive compensation, comprehensive benefits, and professional growth opportunities within a global organization.
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. The Company is fully committed to ensuring equal pay opportunities for equal work regardless of color, race, sex, national origin, sexual orientation, religion, age, veteran status, disability, pregnancy, citizenship status, genetic information, or any other basis protected by federal, state, or local pay equity laws. You do not need to disclose your criminal history or participate in a background check un