Senior Director, Strategy & Planning

Win; New York (NY); Hybrid; USD 81,000 - 99,000; Full time

Job summary

Win is seeking a Senior Director, Strategy & Planning in New York. Hybrid work model. You will translate strategic priorities into measurable outcomes and partner with executive leadership to drive accountability and enterprise-wide initiatives.

The role requires 8+ years in strategy, operations, planning or related leadership, with strong analytical and stakeholder management skills. You will develop executive dashboards and KPIs to support decision-making across functions.

Qualifications

• Bachelor's degree in business administration or related field.
• 8+ years in strategy, operations, planning, or related leadership.
• Proven track record leading enterprise-wide initiatives.
• Strong analytical, communication, facilitation, and stakeholder management skills.
• Experience creating executive dashboards, KPIs, and data-driven reports.
• Highly organized with the ability to manage competing priorities in a fast-paced environment.
• Strategic thinker who can influence outcomes and build alignment.

Responsibilities

• Lead execution of enterprise-wide strategic priorities and major initiatives.
• Maintain org workplans with goals, milestones, metrics, risks, and accountability.
• Facilitate executive reviews and strategic planning sessions to monitor progress.
• Lead cross-functional projects driving organizational effectiveness.
• Develop executive dashboards, KPI reporting, and performance analytics for decisions.
• Align departmental objectives with Win's strategic goals.
• Monitor risks, corrective actions, and mitigation strategies.
• Prepare executive presentations and briefing materials across departments.

Skills

Strategic planning

Executive communication

Cross-functional leadership

Performance analytics

Education

Bachelor's degree in business administration or related field

Master's degree preferred

Job description

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.