Director of Technology Product Delivery
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Posted: 10/19/2026Core Competencies
Role fitCore Competencies
Use this summary to align your resume positioning with the role.
Demonstrates expertise in leading product delivery and transformation initiatives within complex organizations, emphasizing Agile methodologies, technology cost-tracking, and effective stakeholder communication. Proficient in managing cross-functional teams and leveraging delivery metrics to drive measurable outcomes.
Highest-signal resume keywords
Agile Delivery ManagementJira ProficiencyProduct Management ExpertiseStakeholder LeadershipAI-Assisted Technology Implementation
Tech Stack
Tools & technologiesAbout the role
Key responsibilities & impact- Lead the delivery system supporting Hiscox USA’s business
- Lead transformation from project-oriented delivery toward empowered, product-centric teams
- Connect strategy, investment, capacity and execution across Product, Engineering, Quality Engineering, Architecture, Data, Cloud, Cybersecurity, Finance, business functions and strategic partners
- Own integrated delivery across value-stream roadmaps, enterprise programs, modernization initiatives, regulatory commitments and Group imperatives
- Coordinate complex initiatives across teams, platforms, business units and vendors
- Manage, coach and develop direct reports, primarily Agile Delivery Leads and Technical Business Analysts
- Own delivery measurement using Jira as the primary source for delivery insight
- Monitor commitment reliability, capacity, backlog health, carryover, cycle time, throughput, work in progress, aging work and rework
- Diagnose systemic constraints and lead corrective actions
- Establish operating cadence for delivery health, forecast confidence, capacity, risks and improvement actions
- Improve flow across discovery, design, engineering, quality, security, release and adoption
- Own Agile Cost Tracking methodology, including cost rates, initiative classification, Run/Grow/Transform categorization and capitalization treatment
- Partner with Finance, Accounting and Audit on rules, reconciliation, controls and auditability
- Own portfolio-level demand, capacity, budget, vendor expenditure, forecasts and value-realization reporting
- Lead responsible adoption of AI-assisted and agentic technologies across the SDLC
- Build capability in problem framing, context engineering, specification-driven development, agent orchestration, evaluation and human oversight
- Measure AI-enabled practices against cycle time, quality, rework, stability, cost, developer experience and business outcomes
- Embed security, privacy, architecture, regulatory, legal and operational controls into delivery workflows
- Ensure releases have ownership, business readiness, support arrangements and transition into product and service ownership
Requirements
What you’ll need- Significant senior leadership experience in product delivery, technology delivery, product operations or a comparable role within a complex organization
- Accountability for measurable outcomes across multiple teams, portfolios and major initiatives
- Experience coordinating delivery across multiple product teams and major initiatives
- Experience managing and developing delivery professionals
- Experience creating an effective operating model across employees, offshore vendor resources and strategic partners
- Experience transitioning from project- or feature-oriented delivery to durable, empowered product teams
- Experience coordinating portfolios combining product roadmaps, transformation programs, platform modernization, regulatory work and enterprise initiatives
- Proficiency using delivery management platforms such as Jira
- Experience using Jira data and delivery metrics to identify systemic constraints and measure improvement
- Experience owning technology cost-allocation or Agile cost-tracking methods
- Strong understanding of product management, continuous discovery, Agile, Lean, DevOps and outcome-based planning, including OKRs or comparable approaches
- Technical fluency across architecture, APIs, cloud platforms, CI/CD, automated testing, observability, security and operational readiness
- Experience leading responsible AI-assisted or agentic technologies across multiple SDLC stages
- Experience managing direct reports, including coaching, performance management and career development
- Experience leading distributed teams and working with offshore vendor resources
- Experience with vendor management, financial management, workforce planning and portfolio capacity management
- Exceptional stakeholder leadership, executive communication, facilitation, conflict resolution and relationship-building skills
- Significant experience in P&C insurance, financial services or another complex, highly regulated industry
- Preferred: core-system replacement or modernization, cloud migration, API standardization, shared-platform adoption, product operating model transformation, data products, AI-enabled products, Jira Product Discovery, Azure DevOps, Confluence, Miro, product analytics, data visualization and portfolio-management tools
Benefits
Comp & perks- Competitive salary and bonus (based on personal & company performance)
- 401(k) with competitive company matching
- Comprehensive health insurance, vision, dental and FSA plans (medical, limited purpose, and dependent care)
- Company paid group term life, short-term disability and long-term disability coverage
- Paid parental leave
- 4 week paid sabbatical after every 5 years of service
- Financial Adoption Assistance and Medical Travel Reimbursement Programs
- Annual reimbursement up to $600 for health club membership or fees associated with any fitness program
- 2024 Cigna’s Well-Being Award best-in-class health and wellness program
- Dynamic, creative and values-driven culture
- Modern and open office spaces, complimentary drinks
ATS Keywords
✓ Tailor your resumeApplicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard Skills
Product DeliveryTechnology DeliveryAgile Cost TrackingContinuous DiscoveryLean MethodologiesDevOps PracticesPortfolio Capacity ManagementSystemic Constraint DiagnosisOperational ReadinessPerformance Management
Soft Skills
Executive CommunicationConflict ResolutionRelationship BuildingCoachingFacilitation
Tools & Technologies
JiraAzure DevOpsConfluenceMiroData Visualization Tools
Industry Keywords
P&C InsuranceFinancial ServicesRegulatory ComplianceCloud MigrationAPI Standardization