Head of IT Delivery

Who We Are

SiriusPoint is a specialty underwriter providing solutions to clients and brokers around the world. Bermuda-headquartered with offices in New York, London, Stockholm and other locations, we are listed on the New York Stock Exchange (SPNT). We have licenses to write Property & Casualty and Accident & Health insurance and reinsurance globally. Our offering and distribution capabilities are strengthened by a portfolio of strategic partnerships with Managing General Agents and program managers. With over $3.0 billion total capital, SiriusPoint’s operating companies have a financial strength rating of A from AM Best, Fitch and S&P, and A3 from Moody’s.

Join Our Team

We are seeking a Head of IT Delivery to lead SiriusPoint’s 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.

Your responsibilities will include:

Portfolio & Strategic Delivery

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.

Program & Project Delivery

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.

Resource & Financial Management

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.

Delivery Governance & Operational Excellence

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.

Leadership & Stakeholder Management

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.

Your skills and abilities should include:

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.

We aim to retain and attract great people, knowing they can achieve a rewarding and enriching career. We offer a competitive and above market compensation package. The following are some of the benefits and perks we offer our employees:

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

Our CCPA Job Applicant Policy is found here: Sirius-America-CA-Job-Applicant-Privacy-Policy-Final.pdf

SALARY: The estimated annual salary range for this position is mentioned below. This is a good-faith assessment of the salary range for this position only. In determining the actual salary within this range, SiriusPoint will consider a candidate’s relevant experience, location, and other job-related factors.

SALARY RANGE$265,000—$285,000 USD

United behind common goals

At SiriusPoint we work as one team across our global business, and we unite that team behind common goals, understanding the positive impact we can all make at SiriusPoint. We aim to retain and attract great people, knowing they can achieve a rewarding and enriching career.

Our Purpose is to provide security and resilience in an uncertain world.

Our Vision is to be recognized as a best-in-class underwriter utilizing deep risk capabilities to protect our customers. Blending our talent, expertise, and data to provide intelligent risk solutions.

Our culture is one of performance and accountability. Our people are our experts, and you will be empowered to apply your expertise in a supportive, collaborative and purposeful environment.

Our Values are at the heart of our business, and which guide everyday actions and decision making.

Integrity: Integrity, respect and trust are our core principles

Customer Focused: Our customers are the reason we exist

Solution Driven: Creating solutions is our mindset

Diversity: Diversity, inclusion and allyship make us stronger

Collaboration: Collaboration drives outperformance

Why Should You Join SiriusPoint?Our people are our experts, and from day one you will be empowered to apply your expertise in a supportive, collaborative, and purposeful environment. Our Values - Integrity, Customer Focused, Solution Driven, Diversity, and Collaboration - are at the heart of our business, and they guide our everyday actions and decision making. We also unite our global team behind common goals, ensuring you can make a meaningful impact.

We Achieve More TogetherAt SiriusPoint, we know that diversity, inclusion and allyship make us stronger. We value and are committed to supporting the unique voices, backgrounds, cultures, lifestyles, and contributions of the diverse global employee base that make up our business.

We know that a diverse and equitable culture, where all voices are included and heard, is critical to our success as an employer. We are committed to developing our DE&I strategy to ensure that SiriusPoint remains a supportive and empowering place of work.

SiriusPoint’s Talent Acquisition Team values the candidate experience at every stage. It has come to our attention that individuals may be impersonating SiriusPoint recruiters in an effort to obtain money or personal information from job seekers. Please be advised that official communications from SiriusPoint recruiters will originate from authorized SiriusPoint email accounts (ending in @siriuspt.com)", and legitimate employment opportunities can be found through our official careers page (https://job-boards.eu.greenhouse.io/) and authorized recruiting channels: https://www.linkedin.com/company/sirius-point/jobs/

SiriusPoint will never:

Request payment, checks, wire transfers, banking information, or financial account credentials as a condition of employment.

Ask candidates to purchase equipment on our behalf.

Ask candidates to send sensitive personal information, such as Social Security numbers, banking information, or government identification documents, as part of unsolicited recruiting outreach or before a legitimate offer and onboarding process.

SiriusPoint conducts interviews through recognized business communication channels and does not make employment offers without an appropriate interview and evaluation process.

If you believe you have been contacted by someone posing as a SiriusPoint employee, please contact the Talent Acquisition team at TalentAcquisition@siriuspt.com. You should also report the profile to LinkedIn using this online form: Contact form | LinkedIn Help

You may also report suspected fraud to the U.S. Federal Trade Commission at ReportFraud.ftc.gov or the FBI's Internet Crime Complaint Center at ic3.gov.

We are unable to sponsor or take over sponsorship of an employment visa at this time.