Director, Product and Agile Delivery

Company Overview

Travel Insured International (TII), a Crum & Forster company, is a leading travel insurance provider with more than 30 years in business. As a key component of our Specialty Business Unit within the Accident & Health division, TII provides travel protection plans that help each individual travel confidently. We offer products to consumers and to agency partners of all sizes, committed to providing dependable coverage, great value, and end-to-end satisfaction for all customers.

Travel Insured International is hiring a Director, Product and Agile Delivery. This senior people leader will oversee Product Owners, Business System Analysts, Release Train Engineers, and Scrum Masters to orchestrate and mature the full product delivery operating model across multiple squads and value streams. The manager ensures Product Owners own backlog strategy and acceptance, Scrum Masters optimize team flow, and the RTE manages cross‑team dependencies, PI planning, and program‑level execution.

The role serves as the connective tissue between Product Management, Systems Analysis, Engineering, UX, QA, Compliance, and business stakeholders, ensuring alignment, quality, and flow across the entire SDLC. The ideal candidate will drive highest standards and foster a culture of continuous improvement. The position is preferred hybrid in Glastonbury, CT, or Eatontown, NJ, or 100% remote (Eastern time zone).

• Manage a team of 8‑10 resources.
• Coach Product Owners and Business System Analysts 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.

• Ensure backlogs across all squads are healthy, prioritized, scoped, and tied to measurable outcomes; validate PO/BSA ownership of final acceptance and release sign‑off.
• Establish a unified intake, prioritization, and refinement process to ensure clean flow of work across various roles in the SDLC.

• Oversee Scrum Masters in optimizing flow metrics (WIP, cycle time, throughput, predictability) and removing systemic blockers.
• Oversee the RTE’s orchestration of cross‑team planning, dependency management, and program cadence for all increments.

• 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.
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