Senior Director, Strategy & Planning

Translate Strategy into Execution. Drive Accountability. Accelerate Results.

New York, NY | Hybrid

$89,600

THE ROLE

This role will help transform strategic priorities into measurable outcomes across the organization. The Senior Director will partner closely with executive leadership to drive accountability, oversee enterprise-wide initiatives, strengthen organizational performance, and ensure strategic goals are translated into action. This position serves as a critical link between executive vision and operational execution through planning, performance management, reporting, and cross-functional collaboration.

WHAT YOU WILL DO

• Lead the execution of enterprise-wide strategic priorities and major organizational initiatives.
• Maintain organizational workplans, ensuring alignment on goals, milestones, metrics, risks, and accountability.
• Facilitate executive operating reviews and strategic planning sessions to monitor progress and results.
• Lead cross-functional projects that drive organizational effectiveness and operational improvement.
• Develop executive dashboards, KPI reporting, and performance analytics to support decision-making.
• Align departmental objectives and performance measures with Win's strategic goals.
• Monitor organizational risks, corrective action plans, and mitigation strategies.
• Prepare executive presentations, recommendations, and briefing materials while fostering collaboration across Operations, Finance, IT, Programs, and People & Culture.

WHO YOU WILL BE

• You will hold a bachelor’s degree in business administration, Public Administration, Organizational Leadership, Management, or a related field; a master’s degree is preferred.
• You will bring 8+ years of experience in strategy, operations, planning, consulting, project management, organizational effectiveness, or a related leadership function.
• You will have demonstrated success leading complex, enterprise-wide initiatives involving multiple stakeholders and departments.
• You will possess exceptional analytical, communication, facilitation, and stakeholder management skills.
• You will have experience creating executive dashboards, performance metrics, KPIs, and data-driven reports.
• You will be highly organized with the ability to manage competing priorities in a fast-paced environment.
• You will be a strategic thinker who can influence outcomes, build alignment, and drive accountability without direct authority.
• You will be comfortable partnering with senior leaders and presenting recommendations to executive audiences.