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Role Description

As a leading travel insurance provider with more than 25 years in business, Travel Insured International provides trip protection to help each individual travel confidently. This role will lead Product Owners (PO), Business System Analysts (BSA), Release Train Engineers (RTE) and Scrum Masters (SM), and is a senior people leader responsible for orchestrating and maturing the full product delivery operating model across multiple squads and value streams.

• Manage a team of 8-10 resources.
• Coach PO’s, BSA’s on backlog strategy, outcome based prioritization, story quality, and acceptance authority.
• Maintain visibility into Systems Analyst work, requirements quality, and end to end SDLC activities.
• Elevate PO and BSA capabilities across strategic thinking, user value orientation, and release certification.
• Mentor Scrum Masters to drive high performing agile teams through effective ceremonies, impediment removal, flow optimization, and agile coaching.
• Ensure consistent application of agile frameworks (Scrum, Kanban, SAFe), focusing on predictability, transparency, and continuous improvement.
• Standardize ceremonies (daily stand ups, refinement, sprint planning, demos, retros) across teams to ensure consistency and maturity.
• Oversee the RTE’s management of the Agile Release Train (ART), ensuring cross team alignment, dependency mapping, and risk mitigation.
• Ensure PI Planning, Inspect & Adapt (I&A), System Demos, and ART level ceremonies run efficiently and follow a consistent, scalable structure.
• Drive collaboration between RTE, Product Management, Architecture, and Engineering to maintain a unified program level view of delivery.
• Drive a culture of excellence with clear expectations and performance metrics, documentation, and process reinforcement.
• Develop career paths, skill development plans, and readiness for increased responsibility.

Qualifications

• Bachelor’s degree or equivalent from an accredited institution and 10+ years of relevant experience.
• 7+ years of experience required in Product, Business Analysis, Systems Analysis, or related domains.
• 3+ years of experience leading agile product delivery teams (PO, BSA, Scrum Master, RTE, or related functions).
• Demonstrated experience managing multiple agile teams or running an Agile Release Train.
• Deep understanding of backlog management, agile delivery, program increment planning, and cross team coordination.
• Strong coaching skills across Product Ownership, Scrum Mastery, and RTE practices.
• Exceptional communication, stakeholder alignment, and conflict resolution skills.
• Experience defining and optimizing value streams and team topologies.
• 3-4 years of insurance industry experience is a plus.
• Scaled Agile Framework SAFe certifications are a plus.
• Deep understanding of Agile and Scrum methodologies.
• Knowledge of product ownership best practices.
• Exceptional collaboration ability, problem-solving and analytical skills with attention to detail.
• Excellent communication, leadership, and team-building skills.
• Ability to effectively manage multiple projects simultaneously, drive results and prioritize tasks.

Requirements

• Uphold PO/BSA accountability for certification of all work products across the entire SDLC, including UAT, release readiness, and production deployment approval.
• Ensure cross functional alignment among POs, Systems Analysts, UX, QA, Compliance, and Engineering on definition of ready/done and release standards.
• Serve as the escalation point for roadmap conflicts, cross team dependencies, or delivery risks.
• Partner closely with Product Managers to translate epics, OKRs, and strategic themes into executable scope for the ART and squads.
• Partner with Engineering Managers, Architects, and Business Leaders to ensure clear problem statements, feasibility validation, and outcome definition.
• Implement consistent metrics dashboards for team level and ART level performance (predictability, velocity stability, defects, adoption, cycle time).
• Standardize agile and delivery playbooks across POs, Scrum Masters, and the RTE to mature the operating model.
• Drive continuous improvement through retrospectives, coaching plans, and training programs across the delivery organization.
• Back up for any functions of the collective team.
• Other duties as assigned.

Benefits

• Competitive compensation package.
• Generous 401K employer match.
• Employee Stock Purchase plan with employer matching.
• Generous Paid Time Off.
• Excellent benefits that go beyond health, dental & vision, focused on your whole family’s wellness.
• Career development opportunities, including tuition reimbursement, industry-related certifications, and professional training.
• A dynamic, ambitious, fun and exciting work environment.
• Encouragement of social and community responsibility through matching donation programs and volunteer opportunities.