Director of Technology Product Delivery

About Hiscox Hiscox is a leader in specialist insurance. We seek to provide the best protection and peace of mind for our clients through high quality insurance products, backed with excellent service. We are experts in covering a wide range of personal and commercial risks.

Hiscox

ReinsuranceArt and private clientSpecialityPropertyLocal errors & omissions and commercialGlobal errors and omissionsMarine and energyand Direct products (personalhouseholdcommercial

H

hiscoxgroup.com

1,001-5,000 employees

Insurance

Hamilton

Public Company

126k LinkedIn followers

• 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.
• 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.
• 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.
• 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.
• 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.
• 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, including facilitating a cohesive global workforce 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.

Preferred

• Core-system replacement or modernization while sustaining delivery on existing platforms.
• Cloud migration, API standardization, shared-platform adoption or other initiatives requiring coordinated investment across independently prioritized teams.
• Product operating model transformation in a federated or multinational organization, including experience enabling a cohesive global workforce across onshore, offshore and vendor teams.
• Data products, AI-enabled products or internal technology platforms managed as products.
• Jira Product Discovery, Azure DevOps, Confluence, Miro, product analytics, data visualization and portfolio-management tools.
• The successful candidate will be outcome-oriented, product-minded, enterprise-aware and technically fluent. They will be a pragmatic systems thinker who builds trusted networks, makes trade-offs visible, develops strong leaders, uses data to diagnose and improve the delivery system, and introduces enough structure to enable autonomy without allowing process to become the objective.
• At Hiscox our spirit is in Challenging Convention and everything we do is guided by our Values.
• Courage: Dare to take a risk
• Ownership: Passionate, commercial and accountable
• Integrity: Do the right thing, however hard
• Connected: Together, build something better
• Human: Clear, fair and inclusive

• The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment.
• Please note that this position is hybrid and requires two (2) days in our office weekly**
• 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
• Recipient of 2024 Cigna’s Well-Being Award for having a best-in-class health and wellness program
• Dynamic, creative and values-driven culture
• Modern and open office spaces, complimentary drinks
• Hiscox USA was established in 2006 to focus on the needs underserved and specialty commercial clients via both the regional broker and direct distribution channels and is today the fastest-growing business unit within the Hiscox Group.
• Today, Hiscox USA has a talent force of about 400 employees mostly operating out of 6 major cities. Hiscox USA offers a broad portfolio of commercial products, including technology, cyber & data risk, multiple professional liability lines, media, entertainment, management liability, crime, kidnap & ransom, commercial property and terrorism.
• Work with amazing people and be part of a unique culture