Strategic Planning Director Jobs in Springfield, MA

Enterprise Strategy (part of Enterprise Strategy, Ventures & Innovation)

The Strategic Planning Senior Director is a senior leadership role responsible for driving enterprise strategic planning and ensuring alignment of strategic priorities across businesses, functions, and enterprise initiatives. This individual will work at the intersection of strategy, finance, governance, and transformation, partnering with executive leadership to shape long-term priorities, align investments, and translate strategy into measurable business outcomes.

The role requires exceptional stakeholder management, executive influence, and the ability to navigate a complex, matrixed organization. In addition to leading the enterprise strategic planning function, this individual will serve as a leader across the enterprise strategy function, helping connect strategy, planning, and execution through strong partnership, governance, and organizational alignment.

Beyond strategy formulation, the leader plays a critical role in ensuring enterprise priorities are translated into action by working across business segments, functions, and leadership teams. In partnership with leaders responsible for strategy execution and transformation, this role helps operationalize enterprise strategic priorities by strengthening alignment, driving cross-functional collaboration, and connecting strategy to execution, investment decisions, and measurable outcomes.

The Senior Director serves as a trusted advisor to executive leadership and champions an enterprise-wide perspective that enables the organization to deliver differentiated value for customers, clients, providers, and shareholders.

• Drive the annual enterprise strategic planning process, ensuring alignment across business, functional, financial, and portfolio planning processes.
• Coordinate development of multi-year strategic plans and strategy-linked financials across growth platforms, businesses, and enabling functions.
• Partner with Finance to integrate strategic priorities, financial scenarios, capital allocation considerations, and funding decisions.
• Facilitate planning forums, financial assumption reviews, cross-functional alignment sessions, and executive governance meetings.
• Synthesize business inputs into enterprise-level strategic insights, planning materials, executive presentations, and Board-ready communications.
• Identify, frame, and address critical strategic questions facing the enterprise through rigorous analysis and executive-level recommendations.
• Monitor emerging opportunities, risks, dependencies, and enterprise tradeoffs to support strategic decision-making and portfolio prioritization.
• Lead continuous improvement of the strategic planning process, operating model, and stakeholder engagement approach.

• Partner closely with transformation and execution leaders to translate enterprise strategy into actionable priorities, measurable outcomes, and enterprise-wide initiatives.
• Help operationalize strategic objectives by aligning priorities across business segments, functions, and key enterprise initiatives.
• Ensure strategic priorities are effectively cascaded throughout the organization and connected to execution, accountability, and value creation.
• Support governance processes that connect strategy, resource allocation, portfolio management, and transformational investments.

• Serve as a central connector across business units, functions, and enterprise teams to drive strategic alignment and coordinated action.
• Build strong partnerships with leaders across business segments, corporate functions, and shared services organizations to advance shared priorities.
• Champion an enterprise-first mindset by identifying opportunities for leverage, integration, and collaboration across organizational boundaries.
• Facilitate alignment on enterprise decisions that require coordinated action across multiple stakeholder groups.

• Serve as a key leader across the enterprise strategy function, fostering strong connections among strategy leaders and practitioners throughout the organization.
• Foster strategic capability building, best-practice sharing, and collaboration across business and functional strategy teams.
• Strengthen the organization's overall strategic capacity by developing tools, frameworks, and forums that support enterprise thinking and decision-making.
• Manage a pool of senior advisors supporting the enterprise strategy function, including resource planning, project deployment, talent development, and prioritization of strategic initiatives.

• Advise senior executives on strategic opportunities, risks, tradeoffs, and investment decisions.
• Develop compelling executive-level presentations, strategic narratives, and communications that drive understanding and alignment.
• Influence key decisions through a combination of analytical rigor, business judgment, and strong stakeholder engagement.
• Represent Enterprise Strategy in leadership forums and cross-functional governance bodies.

• Bachelor's degree required; MBA or other advanced degree strongly preferred.
• 10+ years of experience in corporate strategy, management consulting, investment banking, private equity, business development, or related strategic leadership roles.
• Demonstrated experience leading enterprise-wide strategy development and strategic planning processes within complex organizations.
• Proven ability to influence senior executives and lead through ambiguity without direct authority.
• Exceptional strategic thinking, problem-solving, and executive communication skills.
• Strong analytical capabilities, including business case development, financial analysis, and strategic evaluation.
• Experience leading large cross-functional initiatives involving multiple stakeholder groups.
• Proven ability to build relationships and drive alignment across matrixed organizations.

• Experience in healthcare, health services, insurance, pharmacy, or adjacent industries.
• Experience involving enterprise transformation, portfolio strategy, growth strategy, or operating model evolution.
• Demonstrated success translating strategy into execution and driving measurable business outcomes.
• Experience developing and leading enterprise-wide communities, councils, or cross-functional networks.

• Enterprise strategy is clear, actionable, and aligned across the organization.
• Strategic priorities are effectively connected to execution, accountability, and measurable value creation.
• Strong partnership exists between strategy, transformation, and business leaders to drive enterprise outcomes.
• Strategic decisions are informed by rigorous insight, market intelligence, financial discipline, and enterprise perspective.
• Cross-functional collaboration and alignment become a competitive advantage for the organization.
• The enterprise strategy function serves as a catalyst for strategic capability, consistency, and partnership across the business.