Director, Product and Agile Delivery

Crum & Forster • Glastonbury, CT

11h • Hybrid

About The Position

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. As part of the C&F Accident & Health Division Specialty Business Unit, we're proud to partner with agencies of all sizes and help them to offer extensive travel protection with major travel insurance benefits as well as non-insurance assistance services. At Travel Insured, we remain steadfast in the commitment to providing dependable coverage, great value, and end-to-end satisfaction for our customers’ travel insurance experience.
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. This role ensures that Product Owners own backlog strategy and acceptance, Scrum Masters optimize team flow and agile ceremonies, and the RTE manages cross team dependencies, PI planning, and program level execution. The manager builds a unified, high performing delivery ecosystem that consistently translates business strategy into high quality, build ready work and predictable, outcome driven releases.
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 be responsible for driving highest standards and fostering a culture of continuous improvement.
This role is preferred hybrid in our Glastonbury, CT, or Eatontown, NJ, or 100% remote (Eastern time zone).

Requirements

• 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.
• 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.

Nice To Haves

• 3-4 years of insurance industry experience is a plus
• Scaled Agile Framework SAFe certifications are a plus

Responsibilities

• 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
• 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.
• 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. Our programs are focused on your whole family’s wellness, including your physical, mental and financial wellbeing
• A core C&F tenet is supporting your career development, so we provide a wealth of ways for you to keep learning, which may include tuition reimbursement, industry-related certifications and professional training to keep you progressing on your chosen path
• A dynamic, ambitious, fun and exciting work environment
• We believe you do well by doing good and want to encourage a spirit of social and community responsibility, matching donation program, volunteer opportunities, and an employee-driven corporate giving program that lets you participate and support your community

What This Job Offers

• Job Type: Full-time
• Career Level: Director