Director of Technology Product Delivery

Hiscox•Atlanta, GA

2d•Hybrid

About The Position

Hiscox is seeking a Director of Product Delivery to lead the delivery system supporting its US business. This senior leader will manage and develop direct reports and create the conditions for durable, cross-functional product teams to solve customer and business problems safely, quickly and sustainably. The role will lead the transition from project-oriented delivery toward empowered, product-centric teams while coordinating enterprise initiatives spanning 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. The role owns the integrated delivery view across value-stream roadmaps and enterprise programs; delivery measurement and continuous improvement; Agile cost tracking and investment reporting; and responsible adoption of AI-assisted and agentic technologies across the software development lifecycle. The position is hybrid and requires two days in the office weekly.

Requirements

Significant senior leadership experience in product delivery, technology delivery, product operations or a comparable role in 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 establishing an operating model across employees, offshore vendor resources and strategic partners.
Experience shifting 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 combining product roadmaps, transformation programs, platform modernization, regulatory work and enterprise initiatives.
Ability to resolve conflicts between local priorities and broader organizational or technology imperatives through transparent investment and capacity decisions.
Proficiency with industry-standard delivery management platforms such as Jira, including analyzing delivery performance and using dashboards and reports to produce actionable insight.
Experience using Jira data and delivery metrics—including commitment reliability, carryover, cycle time, throughput, backlog health, work in progress, allocation and rework—to identify 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.
Experience leading responsible application of AI-assisted or agentic technologies across multiple SDLC stages, with appropriate controls, evaluation, human oversight and impact measurement.
Experience managing direct reports, including setting expectations, coaching, performance management, career development and leadership development.
Experience leading distributed teams and working effectively with offshore vendor resources across time zones, cultures, organizational boundaries and delivery models.
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.

Nice To Haves

Experience with core-system replacement or modernization while sustaining delivery on existing platforms.
Experience with cloud migration, API standardization, shared-platform adoption or initiatives requiring coordinated investment across independently prioritized teams.
Experience transforming product operating models in federated or multinational organizations, including enabling cohesive global teams across onshore, offshore and vendor resources.
Experience managing data products, AI-enabled products or internal technology platforms as products.
Experience with Jira Product Discovery, Azure DevOps, Confluence, Miro, product analytics, data visualization and portfolio-management tools.

Responsibilities

Lead the transition toward empowered product teams with clear outcomes, strategic context, decision boundaries and accountability for customer and business results.
Own an integrated delivery view across value-stream roadmaps, enterprise programs, modernization initiatives, regulatory commitments and Group imperatives.
Create transparent processes for resolving conflicts between local product priorities and broader organizational needs, including decisions on funding, capacity, sequencing and trade-offs.
Coordinate complex initiatives across teams, platforms, business units and vendors, clarifying outcomes, sponsorship, ownership, dependencies, decision paths and success measures.
Build strategic relationships across the organization to anticipate change, surface dependencies, resolve constraints and connect teams with expertise.
Manage, coach and develop direct reports, primarily Agile Delivery Leads and Technical Business Analysts; set expectations, provide feedback, support performance and career development, and shape team topology, workforce plans, sourcing strategy and delivery capability.
Own the delivery measurement system, using 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 delivery platforms and data-analysis capabilities, including reporting, dashboards and filters, to analyze delivery metrics and ensure consistent definitions and reporting across teams.
Diagnose systemic constraints, unreliable data, workflow friction and recurring delivery failures, and lead corrective action with Product, Engineering, Quality and Delivery leaders.
Establish a regular operating cadence to review 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.
Own the Agile Cost Tracking methodology, providing a transparent and defensible view of technology investment by team, initiative and work category.
Maintain team and sprint cost rates, initiative classification, Run/Grow/Transform categorization, capitalization 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 for financial reporting and auditability.
Keep initiative lists, cost rates, allocation logic and capitalization rules current and consistently applied, with appropriate controls and data-quality checks.
Connect delivery cost to outcomes, capacity and realized value to support informed investment and prioritization decisions.
Own portfolio-level demand, capacity, budget, vendor expenditure, forecasts and value-realization reporting within the role’s scope.
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.
Embed security, privacy, architecture, regulatory, legal and operational controls into delivery workflows, emphasizing clear guardrails, automation and traceability.
Ensure releases have clear ownership, business readiness, support arrangements and appropriate transition into ongoing product and service ownership.

Benefits

Competitive salary and bonus based on personal and company performance.
401(k) with competitive company matching.
Comprehensive health insurance, vision, dental and FSA plans, including medical, limited-purpose and dependent-care FSAs.
Company-paid group term life, short-term disability and long-term disability coverage.
Paid parental leave.
Four-week paid sabbatical after every five years of service.
Financial Adoption Assistance and Medical Travel Reimbursement Programs.
Annual reimbursement up to $600 for health club membership or fees associated with a fitness program.
Dynamic, creative and values-driven culture.
Modern and open office spaces and complimentary drinks.