Director of Technology Product Delivery

Hiscox•Boston, MA

3d•$150,000 - $180,000•Hybrid

About The Position

Hiscox is seeking a senior leader to lead the delivery system supporting its US business. The Director 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 shift from project-oriented delivery to empowered, product-centric teams while coordinating enterprise initiatives across value streams. These include 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 Director will own delivery intelligence and continuous improvement, technology investment and Agile Cost Tracking, and responsible adoption of AI-enabled ways of working across the software development lifecycle. The role includes portfolio-level demand, capacity, budget, vendor expenditure, forecasts and value-realization reporting within its scope. The position is hybrid and requires two days in the office each week. Hiscox USA has about 400 employees, mostly operating from six major cities, and offers commercial insurance products to specialty commercial clients.

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 creating an effective 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 that combine product roadmaps, major 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, interpreting dashboards and reports, and turning data into actionable insight.
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.
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 building leadership capability.
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 other initiatives requiring coordinated investment across independently prioritized teams.
Experience with product operating model transformation in a federated or multinational organization, including enabling a cohesive global workforce across onshore, offshore and vendor teams.
Experience with data products, AI-enabled products or internal technology platforms managed 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 the integrated delivery view across value-stream roadmaps, enterprise programs, modernization initiatives, regulatory commitments and Group priorities.
Create transparent processes for resolving conflicts between product priorities and wider organizational needs, including funding, capacity, sequencing and trade-off decisions.
Coordinate complex initiatives across teams, platforms, business units and vendors, defining outcomes, sponsorship, ownership, dependencies, decision paths and measures of success.
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 of transparent 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 such as Jira to analyze metrics through reports, dashboards, filters and other data-analysis capabilities, maintaining consistent definitions and reporting.
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 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.
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 and 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 financial reporting and audit evidence.
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 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 SDLC activities, 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 the impact of AI-enabled practices on cycle time, quality, rework, stability, cost, developer experience and business outcomes.
Embed security, privacy, architecture, regulatory, legal and operational controls in delivery workflows, emphasizing clear guardrails, automation and traceability.
Ensure releases have clear ownership, business readiness, support arrangements and transition to ongoing product and service ownership.
Uphold Hiscox’s values of Courage, Ownership, Integrity, Connected and Human.

Benefits

Competitive salary and bonus based on personal and company performance.
401(k) with competitive company matching.
Comprehensive health insurance, vision and dental plans, and flexible spending accounts for medical, limited-purpose and dependent-care expenses.
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.
Health and wellness program recognized with the 2024 Cigna Well-Being Award.
Dynamic, creative and values-driven culture.
Modern and open office spaces with complimentary drinks.