We stand apart for our outstanding client service, intelligent risk taking and superior risk adjusted returns for our shareholders. We also proudly maintain an entrepreneurial, disciplined and ethical corporate culture. All qualified applicants will receive consideration for employment without regard to any protected characteristic, including age, color, disability, ethnicity, gender identity, marital status, national origin, pregnancy, race, religion, sex, sexual orientation, veteran status, or any basis prohibited by the laws that govern its operations.

Delivery Lead – Infrastructure & IRM How does this role contribute to our collective success?

The Delivery

Lead – Infrastructure & IRM is accountable for the outcomes of AXIS's portfolio of strategic Infrastructure and Information Risk Management (IRM) investments, spanning infrastructure and cloud modernization, network and end-user technology, technology resilience, and cybersecurity capabilities that protect AXIS's businesses and regions globally.

This is a delivery leadership role: it owns the integrated portfolio, ensures investment is focused on the highest-value priorities, and is measured on the resilience, risk reduction, and business value the portfolio delivers. Reporting to the Strategic Delivery Lead – COO, this role drives disciplined portfolio execution across regions and time zones, actively managing dependencies, delivery risk, and investment performance, and gives sponsors and senior leadership transparent, decision-ready insight into what is being delivered, at what cost, and with what result. Working closely with Infrastructure and IRM leadership, the role influences senior stakeholders to make timely decisions and trade-offs, leads the portfolio's shift to product-aligned, Agile ways of working, and translates strategic priorities into delivered capabilities, sustained adoption, and realized benefits.

Lead annual and multi-year Infrastructure and IRM portfolio planning, working with technology leaders to identify demand, shape scope and estimates, determine resource requirements, and sequence initiatives for budget and investment planning. Challenge and shape business cases to ensure investment is directed to the initiatives that deliver the greatest resilience, risk reduction, and business value.

Ensure

Infrastructure and Security dependencies, including environments, connectivity, security, capacity, testing, and implementation, are built into broader business and application programs from the outset.

Drive Disciplined Portfolio Execution

Lead delivery across strategic initiatives covering infrastructure and cloud modernization, network, end-user technology, identity and access management, security operations, and technology resilience across AXIS's regions and business units, ensuring commitments translate into delivered outcomes. Maintain a forward-looking view of portfolio performance, identify slippage early, and take decisive corrective action to protect outcomes, cost, and quality. Own cross-project, cross-regional, and enterprise dependencies, including sequencing and critical path, and resolve conflicts with other COO, Technology, application, and regional programs before they affect delivery.

Oversee design, build, testing, deployment, cutover, and stabilization with infrastructure, security, and business partners, minimizing disruption to production services and the business. Apply commercial judgment in managing third-party and staff-augmentation partners, including SOW development and renewal, commercial and rate-card analysis, contract consumption, partner performance, and opportunities to optimize delivery cost and capacity.

Deliver

Infrastructure, Security, and AI Outcomes Align Infrastructure, IRM, Architecture, and application delivery teams on backlogs, release plans, and capacity so that effort remains focused on portfolio priorities. Drive delivery of prioritized automation and AI use cases, such as infrastructure automation, AIOps and observability, threat detection and response,



and vulnerability management, from discovery through pilot and scaled rollout, with explicit value expectations and go/no-go decisions. Ensure business and security requirements, acceptance criteria, and value expectations are clearly defined and that solutions include security by design, appropriate human oversight, risk management, and controls.

Hold delivery accountable beyond implementation for effective operational handover, sustained adoption, and measurable value. Lead the Shift to Product-Aligned Delivery Lead the transition of Infrastructure and IRM from project-based delivery to persistent, product-aligned Agile teams, in partnership with Infrastructure and IRM leadership and the COO delivery organization, to deliver outcomes faster and more predictably. Implement portfolio intake, prioritization, and capacity allocation across strategic initiatives, run and maintain activities, technical debt, security remediation, and audit findings.

Use delivery and flow measures, such as predictability, cycle time, and throughput, supported by consistent tooling, to provide portfolio visibility and drive continuous improvement.# Manage Investment, Transparency, and Value Realization Own the portfolio investment, including forecasts, actuals, accruals, and variance, in partnership with Finance, and recommend reallocation of funding and capacity as priorities, risks, or performance change. Provide the Strategic Delivery Lead – COO, Infrastructure and IRM leadership, sponsors, and senior leadership with transparent, decision-ready reporting on progress, spend, risk, and value, including a candid view of portfolio health and the decisions required. Define and track outcome measures and baselines for service availability, resilience, security risk posture, cost, and quality alongside delivery KPIs.

Maintain a benefits register and work with Infrastructure and IRM owners to evidence value realization and risk reduction, recommending changes to initiatives that are no longer delivering expected value.

Govern Delivery

Risk and Control Run proportionate, decision-focused portfolio governance, including steering committees, decision logs, and stage gates, ensuring decisions are made at the right level and acted on. Proactively identify, assess, and manage delivery risks, issues, and dependencies, elevate with clear options and recommendations, and drive timely resolution. Manage scope and change control, assessing the impact of changes on outcomes, investment, schedule, and advantages.

Partner with Risk, Compliance, Legal, and Internal Audit to ensure changes maintain effective IT general and security controls and meet regulatory and cybersecurity requirements across jurisdictions. Ensure delivery controls and audit evidence meet COO delivery and enterprise standards.

Influence Senior

Stakeholders and Drive Adoption Act as a trusted advisor to senior business, technology, and risk stakeholders, framing trade-offs in terms of business impact, risk, and cost, and securing timely decisions. Partner with change management and training teams on change impact, readiness, training, and adoption activities.

Success Measures

Committed portfolio outcomes, including milestones, capabilities, and benefits, delivered on time, within budget, and to agreed quality standards. Dependencies and delivery risks identified early and resolved before they affect outcomes. A transparent, trusted, and consistent view of portfolio progress, spend, risk, and value for senior leadership.

Measurable value realization against the benefits case, including improvements in resilience, service availability, security risk posture, cost and quality.



Successful deployment and sustained adoption of infrastructure, security, automation, and AI capabilities consistently across regions, with minimal disruption to production services and supported by effective controls. Product-aligned ways of working adopted across Infrastructure and IRM, evidenced by stable teams, a prioritized portfolio backlog, and more predictable delivery.

Strong sponsor and senior stakeholder confidence, with timely decisions on priorities and trade-offs. No material control issues or audit findings arising from portfolio changes.

Experience and Qualifications Bachelor's degree required. 10+ years of technology delivery leadership experience, including accountability for outcomes across complex, multi-workstream global infrastructure, security, or technology transformation portfolios.

Experience in insurance or reinsurance, with a solid understanding of how infrastructure, cybersecurity, and information risk support underwriting, claims, and corporate functions and meet industry regulatory expectations; Proven track record of disciplined portfolio execution, including managing dependencies, delivery risk, investment, and governance across multiple stakeholders and third-party partners. Demonstrated commercial judgment, including managing significant technology budgets, shaping business cases, managing vendor commercials, and making value-based trade-offs. Track record of influencing senior executives and sponsors and securing decisions, including preparing and presenting executive-level reporting and steering committee materials.

Demonstrated experience delivering across multiple regions, time zones, and regulatory environments, including working with global and regional leadership.

Experience delivering infrastructure modernization, cloud migration, cybersecurity, automation, or AI-enabled solutions, including the related process, control, and change implications.

Experience leading the shift to Agile or product-aligned delivery in infrastructure, security, or operations-focused technology environments.

Key Capabilities

Outcome-oriented delivery leadership: Turns strategy into outcomes, keeps teams focused on value delivered rather than activity completed, and drives disciplined execution to agreed scope, time, cost, and quality.

Commercial judgment: Makes sound investment, vendor, and prioritization decisions, balancing value, cost, and risk. Understands the insurance and reinsurance business and how infrastructure, security, and information risk capabilities protect and enable it.

Senior stakeholder influence: Builds credibility with senior leaders, frames trade-offs clearly, and drives timely decisions across functions and geographies. Anticipates risks and dependencies, resolves issues, and makes sound trade-offs under pressure. Understands how infrastructure, cloud, security, automation, and AI capabilities improve resilience and reduce risk, and what it takes to deliver and adopt them responsib...

In the office three days per week. Flexibility to work across time zones and travel internationally as required. 100,000 - $135,000 CAD. In addition, you will be offered competitive target incentive compensation, with awards based on overall corporate and individual performance.

On top of this, you will be eligible for a comprehensive and competitive benefits package which includes medical plans for you and your family, health and wellness programs, retirement plans, tuition reimbursement, paid vacation, and much more. We are shaping the direction of Insurance and Reinsurance during a critical and exciting time for the industry. Whether you are a student approaching graduation or a seasoned professional looking for a new environment, AXIS has the right challenges and career opportunities for you.

We offer a comprehensive and competitive benefits package which includes medical plans for employees and their families, health and wellness programs, retirement plans, tuition reimbursement, paid vacation, and much more. #

📌 Delivery Lead - Infrastructure/Irm (Winnipeg)
🏢 AXIS Re
📍 Winnipeg