Remote Risk Management Jobs in Madison, CT (NOW HIRING)

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 to help each individual travel confidently.

Travel Insured International is proud to offer products to consumers and to agency partners of all sizes. We're committed to providing dependable coverage, great value, and end-to-end satisfaction for all customers.

Travel Insured International (TII), is hiring a Director, Product Management

As a leading travel insurance provider with more than 30 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.

We are looking for an experienced Director of Product Management to own and drive the direct-to-consumer digital product experience at TII. This is a product leadership role, not a delivery management role. You will define what we build, why we build it, and how we measure success - leading a team of Product Owners who translate product strategy into high-quality, outcome-driven releases across our D2C web application and B2B partner distribution channels.

You will serve as the connective tissue between business strategy, engineering, UX, QA, compliance, and our distribution partners - holding the team to a high bar on product quality, user value, and delivery predictability. This role reports into the VP, Digital Transformation and is part of an active technology modernization program.

This role is preferred hybrid in our Glastonbury, CT, or Eatontown, NJ, or 100% remote (Eastern time zone).

What you will do:

Product Strategy & Roadmap

• 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.

Product Ownership & Team Leadership

• 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.

Delivery Partnership & Execution

• 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.

D2C Web Application Delivery

• 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.

Implementation & Modernization Backlog Ownership

• 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.

Quality & SDLC Accountability

• 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.

Measurement & Continuous Improvement

• 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

What you will bring to C&F

• 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

#LI-MS

#LI-REMOTE

• 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

At C&F you will BELONG

If you require special accommodations, please let us know. We value inclusivity and diversity. We are committed to equal employment opportunity and welcome everyone regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, or Veteran status. If you require special accommodations, please let us know. Belonging at C&F, is a mindset. It's about fostering a culture of inclusion and connection, where everyone feels valued, heard, and empowered to thrive and where our social impact efforts help strengthen the communities where we live and work.

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Crum & Forster is committed to ensuring a workplace free from discriminatory pay disparities and complying with applicable pay equity laws.  Salary ranges are available for all positions at this location, taking into account roles with a comparable level of responsibility and impact in the relevant labor market and these salary ranges are regularly reviewed and adjusted in accordance with prevailing market conditions. The annualized base pay for the advertised position, located in the specified area, ranges from a minimum of $100,800 to a maximum of $170,500. The actual compensation is determined by various factors, including but not limited to the market pay for the jobs at each level, the responsibilities and skills required for each job, and the employee's contribution (performance) in that role. To be considered within market range, a salary is at or above the minimum of the range. You may also have the opportunity to participate in discretionary equity (stock) based compensation and/or performance-based variable pay programs.