Digital Delivery

Healthy Paws is Chubb's pet insurance growth business and one of the largest direct to consumer pet insurance brands in the country. The Digital Delivery Lead owns agile delivery for the Healthy Paws team from planning through production. The role works with product, technology, and partner teams to keep work on schedule and to meet enrollment and retention goals.

The ideal candidate has strong SAFe experience, solid Agile and Product Lifecycle delivery experience, and the facilitation skills to work with both technical and business partners. The role also works with IT and other technical teams to bring AI into delivery workflows and project documentation in practical, repeatable ways.

KEY RESPONSIBILITIES

• Actively facilitate/lead program increment planning, backlog refinement, sprint planning, stand ups, reviews, and retrospectives for the Healthy Paws delivery teams.

• Combine team level PI objectives into program PI objectives and publish them for Healthy Paws and PRS leadership.

• Maintain the PI calendar and design ceremonies that keep teams aligned.

• Own release planning from commit to deployment, including readiness reviews, cutover planning, and post release reviews for Healthy Paws features and integrations, working with IT, MarTech, and vendors.

• Maintain a prioritized program backlog with the Healthy Paws product head and the integrated pod team.

• Track sprint priorities and PI level velocity, burn down, and predictability against growth goals, and report them to leadership with recommended actions.

• Identify, map, and resolve dependencies across Healthy Paws engineering, lead aggregator partners, partner integration teams (including API and platform IT partners), and other third party vendors.

• Coordinate deployment timing across partner teams to avoid late conflicts that affect enrollment flows or policy servicing.

• Serve as the escalation path for cross team blockers, and bring a proposed resolution with each one.

• Serve as the single point of contact for production defects and manage communication with aggregators, third parties, and sponsorship partners.

• Collaborate with Head of AI to build, use, train and promote AI tools within Healthy Paws delivery, including backlog enrichment, retrospective analysis, dependency detection, and automated reporting.

• Coach team members at different levels of agile maturity and promote consistent agile practices.

• Support continuous improvement and experimentation, with retrospectives focused on operational efficiency and annual growth goals.

• Publish data driven delivery updates to Healthy Paws and PRS leadership on digital store health, PI predictability, risks, and milestones.

• Present delivery status in terms business and executive audiences can act on, and report progress against goals and ROI on a regular basis.

• Work with Healthy Paws product, marketing, and CX leads so delivery sequencing reflects pet enrollment and retention priorities.

REQUIRED

• 6 or more years of agile delivery experience, with at least 3 years as a lead, scrum master, or release train engineer.

• Experience planning and facilitating PI Planning in a SAFe or comparable scaled agile environment.

• Experience managing cross team dependencies in matrixed or multi vendor organizations.

• Proficiency with Jira, Azure DevOps, or comparable agile delivery tools.

• Ability to communicate delivery health, risks, and trade offs to senior leadership.

• SAFe Scrum Master (SSM), SAFe Advanced Scrum Master (SASM), or PMP certification, or equivalent demonstrated expertise.

PREFERRED

• Experience in insurance, pet health, or a high volume direct to consumer digital business.

• Familiarity with D2C enrollment flows, API based partner integrations, and digital acquisition technology stacks.

• Hands on experience with AI assisted delivery tools, such as AI supported backlog refinement, automated retrospective summaries, or dependency detection.

• Experience in co-sourced delivery models with onshore and offshore team members.

• Exposure to subscription or recurring revenue business models where renewal and retention matter as much as acquisition.

MEASURES OF SUCCESS

• PI objectives are met or exceeded consistently.

• Impediments are resolved before they affect enrollment or servicing flows.

• Dependencies across Healthy Paws engineering and partner teams are tracked in real time and known well before sprint end.

• Engineering, product, and business stakeholders work from one shared view of delivery health and digital store priorities.

• AI is used in two or three team processes within the first two quarters, with measurable impact on throughput or quality.

• Team members find the ceremonies valuable.

The pay range for the role is $143,000 to $189,000. The specific offer will depend on an applicant’s skills and other factors. This role may also be eligible to participate in a discretionary annual incentive program.  Chubb offers a comprehensive benefits package, more details on which can be found on our careers website.  The disclosed pay range estimate may be adjusted for the applicable geographic differential for the location in which the position is filled.