Head of Enterprise PMO

Join Our Team    

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. The role will span across two core capabilities: one focused on ensuring disciplined financial and resource tracking are maintained to enable delivery – managing funding, value realisation, people; the other dedicated to maintaining the integrity of the transformation portfolio through strong governance and adherence to change frameworks, creation and maintenance of controls, insightful reporting, and proactive risk and issue management. Together, these capabilities underpin the Enterprise PMO’s ability to drive consistent, high-quality outcomes across our change agenda. 

Responsibilities:

The candidate will focus on the following areas of work:  

• 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.  

 

Your skills and abilities should include: 

• 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. 

 

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