Director of Technology Product Delivery

Job Type:

Permanent

Build a brilliant future with Hiscox

Director of Technology Product Delivery

About the Role:

Hiscox is seeking a Director of Product Delivery to lead the delivery system supporting our US business. This senior leader will manage and develop direct reports while creating the conditions for durable, cross-functional product teams to solve meaningful customer and business problems safely, quickly and sustainably.

The role will lead our transition from project-oriented delivery toward empowered, product-centric teams while coordinating enterprise initiatives that span value streams, including core-system replacement, cloud migration, standardized APIs, platform modernization and Group priorities. The Director will connect strategy, investment, capacity and execution across Product, Engineering, Quality Engineering, Architecture, Data, Cloud, Cybersecurity, Finance, business functions and strategic partners.

Primary Responsibilities:

1. Product Delivery and Organizational Transformation:

• •Lead the transformation toward empowered product teams, giving teams clear outcomes, strategic context, decision boundaries and accountability for customer and business results.
• •Own the integrated delivery view across value-stream roadmaps, enterprise programs, modernization initiatives, regulatory commitments and Group imperatives.
• •Create transparent mechanisms to resolve conflicts between local product priorities and broader organizational needs, including explicit decisions on funding, capacity, sequencing and trade-offs.
• •Coordinate complex initiatives across teams, platforms, business units and vendors, ensuring clear outcomes, sponsorship, ownership, dependencies, decision paths and measures of success.
• •Maintain a strong network of strategic relationships across the organization to anticipate change, surface dependencies, resolve constraints and connect teams with the right expertise.
• •Manage, coach and develop direct reports, primarily Agile Delivery Leads and Technical Business Analysts; set clear expectations, provide regular feedback, support performance and career development, and shape team topology, workforce plans, sourcing strategy and delivery capability.

2. Delivery Intelligence and Continuous Improvement:

• •Own the delivery measurement system and use Jira as the primary source for transparent, repeatable and actionable delivery insight.
• •Monitor committed versus completed work, capacity and over-allocation, backlog depth and readiness, carryover, cycle time, throughput, work in progress, aging work and rework trends.
• •Use industry-standard delivery platforms, such as Jira, to analyze delivery metrics through reporting, dashboards, filters and other data-analysis capabilities, ensuring definitions and reporting are consistent across teams.
• •Diagnose systemic constraints, unreliable data, workflow friction and recurring delivery failure patterns, then lead corrective action with accountable Product, Engineering, Quality and Delivery leaders.
• •Establish a regular operating cadence for reviewing delivery health, forecast confidence, capacity, risks and improvement actions with teams and senior leaders.
• •Improve end-to-end flow across discovery, design, engineering, quality, security, release and adoption through smaller increments, earlier feedback and proportionate governance.

3. Technology Investment and Agile Cost Tracking:

• •Own the Agile Cost Tracking methodology end to end, providing a transparent and defensible view of technology investment by team, initiative and work category.
• •Maintain the methodology for team and sprint cost rates, initiative classification, Run/Grow/Transform categorization, capitalizable versus expense treatment, delivery or go-live dates and required Jira metadata.
• •Partner with Finance, Accounting and Audit to define rules, validate assumptions, reconcile outputs and maintain evidence that supports financial reporting and auditability.
• •Ensure initiative lists, cost rates, allocation logic and capitalization rules remain current, consistently applied and supported by appropriate controls and data-quality checks.
• •Connect delivery cost to outcomes, capacity and realized value so value-stream owners and executives can make informed investment and prioritization decisions.
• •Own portfolio-level demand, capacity, budget, vendor expenditure, forecasts and value-realization reporting within the role’s scope.

4. Modern Engineering and AI-Enabled Ways of Working :

• •Strengthen continuous discovery and iterative delivery through customer insight, operational expertise, experimentation, prototypes, telemetry and early exposure of working software.
• •Lead responsible adoption of AI-assisted and agentic technologies across the SDLC, including discovery, specification, engineering, code review, testing, security, documentation and release.
• •Build capability in problem framing, context engineering, specification-driven development, agent orchestration, evaluation and human oversight.
• •Measure whether AI-enabled practices improve cycle time, quality, rework, stability, cost, developer experience and business outcomes rather than focusing on tool adoption alone.
• •Embed security, privacy, architecture, regulatory, legal and operational controls into delivery workflows, favoring clear guardrails, automation and traceability over unnecessary approval gates.
• •Ensure releases have clear ownership, business readiness, support arrangements and appropriate transition into ongoing product and service ownership.

Required Experience and Capabilities:

• •Significant senior leadership experience in product delivery, technology delivery, product operations or a comparable role within a complex organization, with accountability for measurable outcomes across multiple teams, portfolios and major initiatives.
• •Demonstrated success coordinating delivery across multiple product teams and major initiatives, managing and developing delivery professionals, and creating an effective operating model across employees, offshore vendor resources and other strategic partners.
• •Experience moving an organization from project- or feature-oriented delivery toward durable, empowered product teams, with evidence of improved decision-making, flow, predictability or business outcomes.
• •Experience coordinating portfolios that combine product roadmaps, major transformation programs, platform modernization, regulatory work and enterprise initiatives.
• •Proven ability to resolve conflicts between local priorities and wider organizational or technology imperatives through transparent investment and capacity decisions.
• •Proficiency using industry-standard delivery management platforms, such as Jira, to analyze delivery performance, interpret dashboards and reports, and turn data into actionable insight.
• •Demonstrated experience using Jira data and delivery metrics such as commitment reliability, carryover, cycle time, throughput, backlog health, work in progress, allocation and rework to identify systemic constraints, lead corrective action and measure improvement.
• •Experience owning technology cost-allocation or Agile cost-tracking methods, including team or sprint cost rates, initiative allocation, capitalization and expense treatment, data-quality controls, reconciliation and partnership with Finance, Accounting or Audit.
• •Strong understanding of modern 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.
• •Demonstrated experience leading the responsible application of AI-assisted or agentic technologies across multiple stages of the SDLC, including appropriate controls, evaluation, human oversight and measurement of impact on cycle time, quality, rework, stability, cost or developer experience.
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