Director, Product Management

Crum & Forster is a leading travel insurance provider with over 30 years of experience, and they are seeking a Director of Product Management to lead the direct-to-consumer digital product experience at Travel Insured International. The role involves defining product strategy, leading a team of Product Owners, and ensuring high-quality product delivery across various channels.

Responsibilities:

• Define and own the product roadmap for TII’s direct-to-consumer web application, grounded in customer insights, business goals, and competitive context
• Translate executive strategy, OKRs, and commercial priorities into a coherent, sequenced product backlog with measurable outcomes
• Partner with business leaders, marketing, and distribution stakeholders to align roadmap to revenue and retention goals
• Own the product vision for our D2C and B2C Application and partner integration layer
• Lead a team of 8–10 Product Owners across multiple squads
• Establish and enforce high standards for backlog health, story quality, acceptance criteria, and release readiness
• Coach POs to own outcome-based prioritization, UAT, and production sign-off — not just backlog administration
• Develop career paths and growth plans across the product organization
• Partner with engineering managers, architects, and UX to ensure features are feasible, well-defined, and ready to build
• Serve as the escalation point for roadmap conflicts, cross-team dependencies, and delivery risk
• Maintain a healthy, forward-looking pipeline of work across squads; drive intake, prioritization, and refinement processes
• Support PI planning and program-level coordination in partnership with the Release Train Engineer — with a focus on outcomes over ceremony
• Own the end-to-end product delivery of TII’s direct-to-consumer web application — from discovery and design through release and iteration
• Drive feature definition, prioritization, and acceptance for consumer-facing experiences including quoting, purchasing, policy management, and claims entry
• Partner with UX and engineering to translate customer needs into well-scoped, build-ready stories that ship with quality and measurable impact
• Maintain a deep understanding of the D2C funnel — conversion rates, drop-off points, session behavior — and use that data to drive backlog decisions
• Ensure the web application roadmap reflects both near-term feature delivery and the longer-term platform investments needed to sustain velocity
• Own derived product backlogs that support platform modernization efforts — re-platforming initiatives, architecture enablers, and technical foundations that unlock future feature velocity
• Translate implementation epics (infrastructure upgrades, API refactors, component migrations) into sprint-ready stories with clear acceptance criteria and business justification
• Work closely with architects and engineering leads to understand technical dependencies and sequence implementation work alongside feature delivery without compromising either
• Own the integration backlog for partner and distribution channel connectivity — including airline partners, GDS systems, and B2B distribution APIs — ensuring integration work is scoped, prioritized, and delivered as a first-class product concern
• Maintain enough technical fluency to ask the right questions of engineering, validate feasibility assumptions, and hold the team accountable to implementation commitments without micromanaging execution
• Ensure implementation backlogs are tied to measurable outcomes — not just engineering tasks — so stakeholders understand why platform work is being prioritized alongside consumer features
• Uphold Product Owner accountability for certification across the full SDLC, including UAT, compliance review, and release readiness
• Ensure shared definitions of ready and done across product, engineering, QA, and compliance
• Drive continuous improvement through retrospectives, metrics, and coaching — not just process documentation
• Implement product and delivery metrics that matter: conversion rates, funnel drop-off, feature adoption, cycle time, and release predictability
• Use data to make prioritization decisions and to hold the team accountable to outcomes, not just output
• Build a culture of experimentation, user empathy, and evidence-based decision making
• Other duties as assigned

Requirements:

• Bachelor's degree or equivalent from an accredited institution and 10+ years of relevant experience
• 5-10+ years of experience in product management or digital product ownership, with meaningful time spent on consumer-facing web applications
• 7+ years owning digital products in a B2C or D2C context — you have shipped features that real customers use and can speak to the outcomes they drove
• 3–5+ years leading teams of Product Owners, with a track record of elevating PO accountability beyond backlog maintenance into true product ownership
• Proven ability to own both feature-level and implementation-level backlogs — you understand that modernization work and consumer features are not separate tracks, they're the same backlog problem
• Enough technical fluency to engage credibly with engineers and architects: you can read an API spec, understand architectural tradeoffs, and write acceptance criteria for enabler work — not just user stories
• Experience owning or contributing to integration-heavy product work — partner APIs, third-party data feeds, distribution channel connectivity, or similar
• Experience managing product delivery across multiple squads simultaneously, with a strong instinct for sequencing and dependency management
• Strong command of backlog strategy and outcome-based prioritization — you can explain why implementation work belongs in the same roadmap conversation as new features
• 3+ years of insurance industry experience is preferred
• Scaled Agile Framework SAFe certifications are a plus