Director, Digital Product Management Office

Job Summary

The Director of the Digital Product Management Office leads the strategic planning, execution, and value delivery of digital products across the enterprise. Operating within the Scaled Agile Framework (SAFe), this leader drives alignment between business strategy and technology execution, ensuring that digital assets deliver measurable outcomes.

This role is accountable for advancing digital experiences across customers, insurance agents, and employees, while also spearheading adoption of emerging technologies, including Generative AI (GenAI). The Director will oversee product management, product ownership, and user experience (UX) functions, fostering a high-performing culture that enables innovation and value realization.

Job Responsibilities

           Strategic Leadership & Portfolio Alignment

• Define and champion the vision and strategy for the Digital Product Management Office, ensuring alignment with enterprise goals and business strategy.
• Drive the enterprise roadmap for digital experiences, embedding GenAI capabilities and modern design practices.Program & Execution Oversight
• Lead Program Increment (PI) Planning, ensuring strategic objectives translate into actionable deliverables across Agile Release Trains (ARTs).
• Partner with Business Owners, Product Owners, and ART leaders to achieve cohesive execution and outcome delivery.
• Govern and monitor product portfolio health, ensuring compliance with regulatory, financial, and operational standards.

  Experience & Innovation

• Provide executive leadership for the User Experience (UX) function, embedding design thinking and human-centered design into product delivery.
• Champion innovation by introducing GenAI and other advanced technologies into digital experiences and business processes.
• Continuously scan industry and insurance market trends to inform strategy and competitive positioning.

  Performance Management

• Establish and track OKRs, KPIs, and value realization metrics across product portfolios to ensure measurable impact.
• Ensure digital adoption, customer/agent satisfaction, and employee experience outcomes improve year over year.
• Report outcomes and insights to senior executives, influencing enterprise strategy and funding decisions.People & Culture Leadership
• Lead, mentor, and inspire product managers, product owners, and UX professionals.
• Build a diverse, inclusive, and high-performing product management culture and discipline grounded in accountability and innovation.

Job Qualifications

• 8+ years of experience in product management, with at least 3+ years in a leadership role within a SAFe or Agile enterprise.
• Proven success in managing enterprise-scale digital products, platforms, or transformation initiatives.
• Deep understanding of SAFe principles, Lean Portfolio Management, and Agile Release Trains.
• Strong business acumen with demonstrated ability to translate strategy into execution.
• Exceptional communication, stakeholder engagement, and change leadership skills.
• Preferred: 
• SAFe PMPO or SPC certification.
• Experience in regulated industries such as insurance, financial services, or healthcare.
• Familiarity with enterprise tools (e.g., Jira Align, Aha!, Azure DevOps).
• SAFe PMPO or SPC certification.
• Experience in regulated industries such as insurance, financial services, or healthcare.
• Familiarity with enterprise tools (e.g., Jira Align, Aha!, Azure DevOps).

Location

• Hybrid - defined as working three or more days per week in the office 

Behavioral Competencies

• Collaborates 
• Communicates Effectively 
• Customer Focus 
• Decision Quality 
• Nimble  Learning 
• Builds Effective Team 
• Business Insight 
• Develops Talent 
• Directs Work 
• Ensures Accountability 
• Manages Complexity 

Technical Skills

• IT Product Management 
• Market Research 
• Agile Project Management 
• Product Development Lifecycle 
• Product Roadmap 
• Product Strategy 
• Software Development 
• Cloud Computing 
• API Development 
• Quality Assurance  
• Data Management and Integration 
• Software Proficiency

This job description describes the general nature and level of work performed in this role. It is not intended to be an exhaustive list of all duties, skills, responsibilities, knowledge, etc. These may be subject to change and additional functions may be assigned as needed by management.

Founded in 1848, Westfield is a global leader in property and casualty insurance, delivering superior risk insights and innovative solutions to customers through a diverse portfolio of insurance products. Westfield underwrites commercial, personal, surety, and specialty lines of coverage through a network of leading independent agents and brokers in the United States and specialty products through Lloyd’s of London Syndicate 1200. As a mutual insurance company with more than 3,000 employees, Westfield has revenues in excess of $4 billion and more than $10 billion in assets.