Senior Director, IT Portfolio Manager

What part will you play? If you’re looking for a place where you can make a meaningful difference, you’ve found it.

The work we do at Markel gives people the confidence to move forward and seize opportunities, and you’ll find your fit amongst our global community of optimists and problem-solvers. We’re always pushing each other to go further because we believe that when we realize our potential, we can help others reach theirs. Join us and play your part in something special! The Senior Director, IT Portfolio Manager is responsible for all aspects of the division’s information technology strategy and associated systems. This includes the direct management of dedicated delivery resources as well as oversight of all aspects of technology support and operations pertaining to the division business functions. This role drives overall technology strategy and directs the planning and implementation of technology related business solutions in support of business application in order to improve cost effectiveness, service quality, and business development.

The Senior Director, IT Portfolio Manager will oversee the strategic planning, execution, and governance of the project portfolio for the Core Technology Services (CTS) organization. Reporting directly to the CTO, this role ensures that CTS initiatives align with organizational priorities, optimizes resource allocation, and delivers business value through disciplined portfolio management. The role is responsible for efficiently delivering key initiatives and maintaining transparent communication across all organizational levels, including executive leadership. The Senior Director, IT Portfolio Manager will lead the strategic planning, execution oversight, and governance of the project portfolio for the Core Technology Services (CTS) organization.  This role is pivotal in ensuring that technology investments are aligned with enterprise priorities, delivered efficiently, and communicated transparently across all levels of the organization—including executive leadership.

Key Responsibilities:

Portfolio Leadership & Governance

• Lead the development and execution of the CTS portfolio strategy in alignment with business goals and the CTO's technology vision.
• Define and manage IT portfolio governance processes, standards, and metrics to ensure consistency, transparency, and accountability.
• Establish and maintain a centralized IT portfolio management function for CTS.
• Lead portfolio planning, prioritization, and resource alignment across Agile and Waterfall initiatives.
• Drive quarterly business reviews (QBRs), portfolio reviews, and executive reporting rhythms.

Executive Communication & Stakeholder Engagement

• Partner with senior business and IT leaders to prioritize initiatives and align project investments with strategic objectives.
• Act as a liaison between executive leadership, technology teams, finance, and business units to drive portfolio transparency and value realization.
• Serve as a key liaison between CTS and business/IT executives.
• Deliver clear, concise updates on portfolio health, risks, and dependencies.
• Develop and execute a communications strategy for internal stakeholders and partners.

Methodology & Delivery Oversight

• Define and enforce consistent project delivery methodologies (Agile, Waterfall, hybrid).
• Monitor and report on the health, performance, risks, and ROI of the IT project portfolio, ensuring that portfolio decisions are informed by data-driven insights and financial analysis, where appropriate.
• Partner with PMO and Agile CoEs to ensure delivery excellence and continuous improvement; l.ead continuous improvement initiatives in portfolio management practices, tools, and methodologies.

Team Leadership

• Manage a team of Project Managers, Release Train Engineers and Scrum Masters, fostering a culture of accountability, transparency, and collaboration, and innovation.
• Provide coaching, performance management, and career development support.

Strategic Alignment

• Collaborate with Enterprise Architecture, Finance, and Business Units to ensure portfolio investments support long-term business goals.
• Influence investment decisions through data-driven insights and scenario planning.

Qualifications

• Education: Bachelor’s degree in Information Technology, Business Administration, or related field required
• 15+ years of experience in IT, with at least 5 years in senior leadership roles overseeing enterprise portfolios, programs, or PMOs; PMP. Agile and/or SAFe certifications a plus.
• IT portfolio, program, or project management, with at least 5 years in a leadership role. Proven ability t