Scrum Master - AI Delivery

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Scrum Master - AI Delivery

PRIMARY PURPOSE: The Scrum Master is responsible for driving predictable, high‑quality delivery across multiple AI initiatives supporting insurance and claims operations. This role serves as a senior Agile delivery leader, reinforcing disciplined Agile practices, protecting sprint commitments, and enabling sustainable delivery velocity in a high‑demand, regulated operational environment. In addition to Scrum leadership, the role applies project management principles to support planning, execution, governance, stakeholder communication, dependency management, risk mitigation, and delivery reporting across complex AI initiatives.

The Scrum Master supports multiple AI delivery teams or complex initiatives working on solutions that directly impact claims workflows, customer experience, financial outcomes, and regulatory compliance. The role operates with a high degree of autonomy, influencing delivery standards, stakeholder expectations, and cross‑team coordination and project execution to ensure successful delivery of strategic business objectives.

ESSENTIAL FUNCTIONS AND RESPONSIBILITIES

• Facilitates and governs Agile ceremonies across one or more AI teams, ensuring Sprint Planning reflects realistic capacity, cross‑team dependencies, and clearly defined objectives grounded in operational priorities. Partners closely with Product Managers/Owners to ensure backlog readiness, story quality, and alignment to claims workflows, system integrations, and compliance requirements prior to sprint commitment.
• Applies project management disciplines to develop and maintain delivery plans, milestone tracking, dependency management, RAID (Risks, Assumptions, Issues, and Dependencies) logs, and governance activities across multiple AI initiatives, ensuring alignment with organizational priorities and delivery timelines.
• Provides advanced delivery oversight using metrics such as velocity, throughput, cycle time, flow efficiency, and unplanned work percentage to identify systemic risks and improvement opportunities. Interprets trends to proactively advise Product and Technology leadership on capacity constraints, delivery trade‑offs, and operational impacts in response to regulatory changes, client escalations, or emergent business needs.
• Anticipates and resolves complex, cross‑functional impediments related to data access, platform integration, security reviews, model validation, vendor dependencies, and shared services. Works directly with Technology, Security, Data, and Architecture leaders to drive resolution, rather than solely escalating issues.
• Coordinates project activities across multiple delivery teams, vendors, and business stakeholders, ensuring alignment of schedules, dependencies, deliverables, and communications throughout the project lifecycle.
• Establishes and reinforces enterprise‑grade Agile delivery discipline, ensuring mid‑sprint scope changes are controlled, exception‑based, and clearly communicated. Coaches stakeholders on the downstream impact of disrupting sprint commitments, supporting informed prioritization decisions at the leadership level.
• Leads continuous improvement efforts beyond the team level by facilitating advanced retrospectives focused on delivery predictability, quality, collaboration effectiveness, and operational outcomes. Actively coaches team members and Product partners, fostering psychological safety, accountability, and maturity in Agile practices across AI initiatives.
• Designs and maintains executive‑level dashboards and reporting, providing transparent visibility into delivery status, risk exposure, and predictability across initiatives. Synthesizes delivery insights into clear narratives that inform leadership decision‑making without creating delivery friction for teams.
• Partners with business and technology leadership to support project governance activities, including executive status reporting, steering committee updates, decision tracking, and change management communications.

ADDITIONAL FUNCTIONS and RESPONSIBILITIES

• Provides mentorship and informal coaching to less experienced Scrum Masters or Agile practitioners, contributing to consistency of Agile practices across the organization.
• Supports the evolution of Agile delivery standards and best practices within AI and analytics delivery.
• Performs other duties as assigned.
• Travel as required.

QUALIFICATIONS

Education & Licensing

Bachelor's degree from an accredited college or university preferred.  Licenses as needed. Project Management Professional (PMP), Certified ScrumMaster (CSM), Professional Scrum Master (PSM), SAFe Scrum Master, or equivalent Agile/Project Management certification preferred.

Experience

Six (6+) years of related experience or equivalent combination of education and experience required. Demonstrated experience supporting complex technical, data or AI-driven delivery teams, preferably within regulated operational environments.  Experience managing cross-functional projects, coordinating multiple workstreams, facilitating executive stakeholder communications, and applying project management methodologies alongside Agile frameworks is strongly preferred.

Skills & Knowledge

• Deep understanding of Agile delivery within regulated industries such as insurance, claims, or financial services
• Strong knowledge of project management principles, including planning, scheduling, risk management, dependency management, governance, and stakeholder communications.
• Advanced facilitation, coaching, negotiation, and conflict resolution skills
• Ability to influence outcomes across matrixed, multi‑LOB enterprise environments
• Strong analytical capability to interpret delivery metrics and translate insights into actionable guidance for leadership
• Experience using Agile and project management tools (e.g., Jira, Azure DevOps, Confluence, Microsoft Project, Smartsheet, or similar) to manage delivery and reporting.

WORK ENVIRONMENT

When applicable and appropriate, consideration will be given to reasonable accommodation.

Mental:  Clear and conceptual thinking ability; excellent judgment, troubleshooting, problem solving, analysis, and discretion; ability to handle work-related stress; ability to handle multiple priorities simultaneously; and ability to meet deadlines

Physical:  Computer keyboarding, travel as required

Auditory/Visual:  Hearing, vision and talking

The statements contained in this document are intended to describe the general nature and level of work being performed by a colleague assigned to this description.  They are not intended to constitute a comprehensive list of functions, duties, or local variances.  Management retains the discretion to add or to change the duties of the position at any time.

Sedgwick is an Equal Opportunity Employer and a Drug-Free Workplace.

If you're excited about this role but your experience doesn't align perfectly with every qualification in the job description, consider applying for it anyway! Sedgwick is building a diverse, equitable, and inclusive workplace and recognizes that each person possesses a unique combination of skills, knowledge, and experience. You may be just the right candidate for this or other roles.