Vice President, Strategy Advancement & Chief of Staff

The Vice President, Strategy Advancement & Chief of Staff serves as a trusted strategic advisor and partner to the President of Insurance and the Insurance Leadership Team.

This role is responsible for advancing the segment's strategic agenda by leading strategic planning, enabling executive decision-making, driving organisational alignment, and ensuring effective execution of the Insurance segment's highest-priority initiatives.

Strategic Planning and Advancement

• Partner with the President of Insurance and Insurance Leadership Team to develop, refine, and advance segment strategy.
• Lead annual and multi-year strategic planning processes.
• Translate strategic priorities into actionable plans, measurable objectives, and execution roadmaps.
• Conduct market, competitive, regulatory, and business analysis to identify opportunities and risks.
• Support strategic investment decisions and business planning activities.
• Ensure alignment between enterprise priorities, segment objectives, and functional strategies.

Strategy Execution and Performance Management

• Establish and oversee mechanisms that connect strategy to execution.
• Develop and monitor strategic objectives, key results, milestones, and performance indicators.
• Lead executive business reviews and strategic progress assessments.
• Identify execution risks, barriers, and dependencies and facilitate resolution.
• Provide visibility into strategic initiative performance and business outcomes.
• Drive accountability for execution across business and functional leaders.

Executive Advisor and Leadership Partner

• Serve as a trusted advisor and thought partner to the President of Insurance.
• Provide strategic counsel and recommendations on business priorities and opportunities.
• Prepare executive communications, business reviews, leadership updates, and board-level presentations.
• Support executive decision-making through analysis, synthesis, and business insights.
• Ensure alignment and follow-through on executive leadership decisions.

Chief of Staff and Governance Leadership

• Lead governance and operating mechanisms for the Insurance Leadership Team.
• Facilitate leadership meetings, strategic planning sessions, and executive forums.
• Drive decision tracking, accountability, and follow-up across key priorities.
• Establish governance processes that improve transparency, alignment, and execution effectiveness.
• Coordinate enterprise and segment initiatives that require executive oversight.

Organizational Effectiveness and Operating Model Leadership

• Partner with business leaders to improve organisational effectiveness and execution discipline.
• Support operating model evolution, governance design, and organisational alignment initiatives.
• Clarify decision rights, accountability structures, and leadership operating mechanisms.
• Identify opportunities to improve collaboration, simplify processes, and increase organisational agility.
• Ensure organisational structures and operating practices support strategic objectives.

Business Transformation and Change Leadership

• Lead high-priority strategic transformation initiatives on behalf of the President of Insurance.
• Partner with Human Resources, Finance, Technology, Operations, and business leaders to execute large-scale organisational and business change.
• Develop implementation plans and governance models that support successful adoption.
• Monitor progress, organisational readiness, and business impact.
• Drive sustainable change that improves business performance and organisational capability.

Stakeholder Management and Cross-Functional Leadership

• Build strong relationships across the Insurance organisation and enterprise functions.
• Influence and align senior leaders around key strategic priorities.
• Serve as a connector across teams to improve collaboration and execution.
• Foster a culture of accountability, partnership, and continuous improvement.

Required Qualifications

• Bachelor's degree.
• 10+ years of progressive leadership experience in strategy, business operations, consulting, healthcare, finance, or a related discipline.
• Experience leading enterprise-wide or business-critical strategic initiatives.
• Demonstrated success influencing executive leadership teams and driving organisational alignment.
• Experience facilitating strategic planning, governance processes, business reviews, and performance management.
• Strong financial, analytical, and problem-solving capabilities.
• Exceptional written, verbal, and executive communication skills.
• Proven ability to lead and influence in highly matrixed organisations.
• Strong executive presence, judgement, and relationship management skills.

Preferred Qualifications

• Master's degree (MBA, MHA, MPH, or related field).
• Health plan, Medicare Advantage, Medicaid, or broader healthcare industry experience.
• Management consulting experience with a leading strategy consulting firm.
• Experience supporting a business president, COO, CEO, or senior executive leadership team.
• Experience leading enterprise transformation, operating model redesign, or organisational effectiveness initiatives.
• Understanding of healthcare economics, insurance operations, provider strategy, clinical operations, and business performance management.
• Experience building strategic planning, governance, and execution management capabilities within large organisations.