Head of Enterprise PMO

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 Fitch, A‑ from AM Best and S&P, and A3 from Moody’s.

Head of Enterprise PMO

The Head of Enterprise PMO will lead the design, implementation, and continuous improvement of SiriusPoint’s enterprise‑wide programme management capability. This role is pivotal in embedding a high‑performing, permanent PMO function ensuring robust governance, delivery assurance, and portfolio visibility across all transformation initiatives. Reporting to the Transformation & Change Director, the Head of Enterprise PMO will lead a permanent team of PMO professionals supported by additional flex capacity aligned to the evolving needs of the change portfolio.

Responsibilities

• Leading the Enterprise PMO function to enable consistent, high‑quality delivery across SiriusPoint’s transformation agenda, ensuring it is scalable, resilient, and strategically aligned.
• Overseeing the planning and execution of funding allocation, business case development, value tracking, people allocation, and supplier engagement across the entire change portfolio.
• Managing governance and reporting processes – including Board, ELT, and SLT updates – to ensure transparency, accountability and timely decision‑making.
• Driving adoption and continued usage of Monday.com Change Portfolio Management software including the identification and delivery of functionality enhancements / builds.
• Maintaining robust portfolio controls and assurance mechanisms, while proactively managing risks, issues, and change metrics.
• Contributing to the development of a high‑performing PMO team, fostering a culture of continuous improvement, collaboration and data‑driven decision‑making.
• Managing pool of project manager resource ensuring delivery approach aligns with controls and our Change delivery methodology.
• Overseeing the creation of accurate and robust business cases for potential Transformation & Change initiatives, ensuring benefit realisation is closely tracked and delivery against planned OKRs is achieved.

Key Skills & Abilities

• Proven leadership in large‑scale programme and project delivery within high‑performing insurance environments, with the ability to direct finance, resourcing, governance and reporting functions effectively.
• Strong financial and resource planning acumen, including hands‑on experience in business case generation, funding models, value tracking and OKRs, and supplier oversight across complex change portfolios.
• Deep expertise in governance and assurance, including executive‑level reporting, portfolio controls, and risk and issue management.
• Exceptional stakeholder engagement and influencing skills, with a track record of building trusted relationships at senior leadership and board levels.
• Demonstrated ability to build and embed enterprise PMO functions, lead cross‑functional teams, and support transformations at scale.
• Experience using Change Portfolio Management software (e.g., Monday.com).
• Bachelor’s degree in business, organisational development, project management or a related field; professional certifications in project and programme delivery (e.g., PMP, PRINCE2, MSP) and/or change management (e.g., Prosci, APMG) are highly desirable.
• 10+ years relevant experience in enterprise PMO leadership, transformation or change delivery roles within large, complex organisations.

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

Salary

Estimated annual salary range: $180,000 – $210,000 USD.

Our Purpose, Vision & Culture

Our purpose is to provide security and resilience in an uncertain world. Our vision is to be recognized as a best‑in‑class insurer and reinsurer utilizing deep risk capabilities to protect our customers. Our culture values performance, accountability, and collaboration. Our core values: Integrity, Customer Focused, Solution Driven, Diversity, and Collaboration.

Legal & Visa

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

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

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