Head of IT Delivery

SiriusPoint • New York, NY

2d • $265,000 - $285,000 • Hybrid

About The Position

SiriusPoint is seeking a Head of IT Delivery to lead its global technology delivery organization and drive execution excellence across the enterprise portfolio. This leadership role is accountable for the successful planning, prioritization, governance, execution, and delivery of technology initiatives that support business growth, regulatory requirements, and strategic transformation. The Head of IT Delivery will oversee portfolio delivery, resource planning, and delivery execution across IT. The successful candidate will work closely with the Transformation Office, Enterprise Architecture, Cyber Security, Data & AI, Infrastructure, Product Leaders, and business stakeholders to ensure predictable, transparent, and value-driven delivery outcomes. You will report to the Chief Information and Technology Officer.

Requirements

• Master’s or bachelor’s degree in business, computer science, computer engineering, electrical engineering, system analysis or a related field of study, or equivalent experience.
• More than 15 years of experience in insurance and reinsurance in various functions, a sound understanding of insurance and reinsurance processes/concepts.
• 10 or more years of experience in at least three disciplines, such as business, information, solution or technical architecture, application development, middleware, information analysis, database management or operations in a multi-tier environment.
• 5 or more years of business experience in strategic and operations planning and/or business analysis.
• Proven track record leading large-scale transformation and technology portfolios.
• Strong financial management, vendor management, and portfolio governance experience.
• Excellent stakeholder management and executive communication skills.
• Familiar with Cloud-based technologies specifically AWS. Deep and up-to-date expertise in SaaS, infrastructure as a service (IaaS), platform as a service (PaaS), SOA, APIs, DevOps and micro services.
• Familiar with information management practices, system development life cycle management (agile, waterfall, hybrid delivery models), IT services management, infrastructure and operations, and EA and ITIL frameworks.
• Exceptional communication skills (verbal and written), presentation skills, soft and interpersonal skills, including teamwork, facilitation and negotiation.
• Strong mathematical skills needed in this area for cost-benefit analysis, budgeting and risk management.
• Exposure and understanding of existing, new and emerging technologies, and processing environments.

Responsibilities

• Lead planning and execution of SiriusPoint’s enterprise IT portfolio.
• Prioritize initiatives based on business value, strategic alignment, regulatory obligations, and resource capacity.
• Manage portfolio roadmaps and enterprise delivery dependencies.
• Ensure delivery commitments support business and transformation objectives.
• Establish and maintain best practices for project, program, and portfolio management.
• Drive consistency of delivery methodologies, governance standards, and execution disciplines.
• Ensure initiatives meet agreed scope, schedule, budget, quality, and business outcome objectives.
• Manage escalation and resolution of delivery risks, issues, and dependencies.
• Develop capacity planning models for resources across internal teams and third-party partners.
• Manage portfolio financials, including budget forecasts, CapEx, OpEx, vendor costs, and benefit realization.
• Provide transparent reporting to executive leadership and governance committees.
• Partner with Architecture and IT Governance teams to ensure adherence to SDLC, architecture standards, and control requirements.
• Establish delivery metrics, KPIs, and executive dashboards.
• Drive continuous improvement in delivery predictability, transparency, quality, and effectiveness.
• Support regulatory, audit, and compliance obligations related to technology delivery.
• Lead IT Delivery functions across SiriusPoint.
• Develop strong partnerships with business executives, transformation leaders, and IT stakeholders.
• Build a culture of accountability, collaboration, and customer-focused execution.
• Manage strategic delivery vendors and system integrators.

Benefits

• Medical
• Dental
• Vision
• FSA Medical and Dependent care
• Health Savings Account (HSA)
• EAP
• Basic Life and AD&D (company paid)
• Basic Long-Term Disability (employer) paid-Taxable income
• Employee paid Long Term Disability(voluntary)
• Company Medical Leave, Parental leave- 8 weeks full pay after 6 months of service
• Voluntary benefits: short term disability, Critical illness, Hospital Indemnity, Accident
• Travel assistance programs Company paid
• 401(k) 6 % safe harbor match, fully vested after two years, pre- and post-tax contributions allowed
• Gym reimbursement
• Legal plan
• Pet Insurance
• Tuition reimbursement
• Generous PTO
• Flexible work arrangement
• Fully stacked pantry on-site
• Team outings
• ERG Groups

What This Job Offers

• Job Type: Full-time
• Career Level: Executive