VP, Planning & Practice

Job Title

VP, Planning & Practices

The VP, Planning & Practices is a key leader within the Transformation & Delivery Office (TDO), responsible for driving disciplined planning and delivery practices across the strategic portfolio. This role leads the mechanisms, standards, tools, and operating rhythms that help programs plan effectively, manage dependencies, maintain execution visibility, and deliver with greater predictability and consistency.

The role is accountable for portfolio planning processes, integrated roadmap management, planning events, delivery standards, and adoption of common tools and ways of working. This leader partners closely with program leaders, business stakeholders, technology teams, finance, and governance partners to improve execution quality and establish a scalable planning and delivery model across Commercial Insurance.

* The title and career band/level for this position are flexible based on the candidate's experience.

Portfolio Planning

• Lead planning processes across the TDO portfolio, including annual and quarterly planning, integrated roadmap development, and major planning events.
• Establish planning standards for scope, milestones, dependencies, resource needs, and execution timelines.
• Coordinate planning across strategic initiatives so priorities, sequencing, and trade-offs are visible and manageable.
• Partner with program leaders to ensure plans are practical, actionable, and aligned to business objectives.

Planning & Operating Rhythm

• Design and run portfolio planning events, including agendas, inputs, outputs, decision points, and follow-up actions.
• Maintain a clear planning and delivery calendar across the TDO, including milestone reviews, roadmap updates, dependency reviews, and execution check-ins.
• Create repeatable planning routines that improve alignment across business and technology teams.
• Ensure planning events results in clear decisions, documented commitments, and actionable next steps.

Delivery Practices & Standards

• Define, implement, and maintain delivery practices that improve consistency across programs, including planning methods, execution controls, status reporting, and dependency management.
• Support agile, waterfall, and hybrid approaches while promoting common standards and language across the portfolio.
• Lead the implementation of AI SDLC approaches, partnering with IT.
• Develop templates, playbooks, and guidance that help teams execute work in a structured and consistent way.

Tools, Reporting & Data Discipline

• Lead adoption of planning and delivery tools, including JIRA and other portfolio management tools used across the TDO.
• Define standards for maintaining plans, milestones, dependencies, and execution data in core systems and reporting tools.
• Improve visibility into roadmap progress, delivery health, and planning quality through dashboards, reporting, and data standards.
• Partner with governance and program teams to ensure management reporting is timely, accurate, and decision useful.

Dependency & Execution Management

• Establish processes for identifying, tracking, and managing cross-program dependencies, key milestones, and execution risks.
• Support teams in surfacing planning issues early and resolving conflicts that could affect delivery timing or outcomes.
• Maintain an integrated portfolio view of delivery commitments, sequencing, and readiness.
• Promote proactive planning practices that improve coordination across multiple work streams and stakeholder groups.

Continuous Improvement & Enablement

• Coach teams on planning standards, delivery practices, and effective use of tools.
• Assess planning effectiveness and identify opportunities to simplify, standardize, and improve ways of working.
• Capture lessons learned from planning cycles and major delivery efforts to continuously strengthen the TDO operating model.
• Support onboarding and enablement for teams adopting TDO planning practices and standards.

Stakeholder Engagement

• Partner closely with leaders across the TDO and key business and technology functions to align planning approaches and improve execution outcomes.
• Communicate planning assumptions, risks, trade-offs, and delivery implications clearly to senior stakeholders.
• Serve as a trusted advisor to the SVP, Governance, Planning & Delivery Practices on planning effectiveness and execution discipline.
• Reinforce a culture of accountability, transparency, and operational excellence across the portfolio.

• Bachelor's degree required, advanced degree preferred.
• Significant experience in program management, portfolio planning, PMO leadership, delivery excellence, or related disciplines.
• Experience in insurance, financial services, or another complex operating environment preferred.
• Demonstrated success leading planning and delivery practices across complex, cross-functional initiatives.
• Strong understanding of program and portfolio management methods, including agile, waterfall, and hybrid approaches.
• Experience with planning standards, governance…