Senior Director, Program Management

The Role: 

The Senior Director of Program Management is responsible for driving strategic execution, visibility, and operational alignment across the company’s most critical initiatives. This leader owns the company-wide roadmap process, ensuring objectives are well-defined, progress is transparent, and execution risks are proactively managed. The ideal candidate is an experienced program manager with strong execution skills and an exceptional ability to lead cross-functional teams while providing strategic insights to the executive team.

Above & Beyond: The Impact You'll Make:

Strategic Roadmap Development & Alignment

• Own the company-wide strategic roadmap process, ensuring clear company objectives, defined outcomes, and accountability.
• Identify gaps between execution plans and strategic priorities, ensuring alignment at all levels.
• Balance delivery commitments with team-led discovery initiatives to drive innovation alongside execution.
• Establish a structured governance model for roadmap prioritization and iteration based on business needs.

Execution of High-Priority Initiatives

• Act as the direct program lead for the company’s most critical initiative, ensuring structured execution, risk mitigation, and real-time adaptation.
• Work cross-functionally to align stakeholders, remove roadblocks, and ensure clear accountability.
• Develop real-time tracking of progress, outcomes, and risks to keep leadership and teams aligned.

Executive-Level Reporting & Insights

• Lead weekly strategic updates with the CEO and executive team, providing concise progress reports, learnings, and blockers.
• Use data-driven insights to highlight execution risks and necessary adjustments to accelerate key initiatives.
• Ensure company-wide visibility into strategic progress through regular reporting, dashboards, and communication channels.

Execution, Risk Management & Change Leadership

• Identify and resolve execution risks before they impact the roadmap, proactively escalating when necessary.
• Challenge teams if roadmaps aren’t addressing strategic objectives or if execution needs adjustment.
• Lead change management efforts, ensuring smooth transitions when new insights impact priorities or new strategic initiatives arise.
• Implement post-mortem reviews and continuous improvement processes to refine execution strategies over time.

Cross-Functional Collaboration & Delivery Enablement

• Ensure all cross-team dependencies are identified and proactively managed to support smooth execution.
• Act as a central orchestrator for high-priority initiatives, aligning product, engineering, marketing, operations, and other key teams.
• Foster a culture of collaborative problem-solving to resolve bottlenecks and accelerate execution.

Best-in-Class Program Leadership and Development

• Build a best-in-class program management function, defining best practices and execution frameworks for company-wide initiatives.
• Partner with finance to align strategic roadmaps with financial planning.
• Mentor and develop a high-performing program management team, fostering a culture of accountability and excellence.
• Leverage tools like Jira and evaluate other program management software to provide real-time visibility into execution, dependencies, and risks.
• Establish standardized reporting and analytics to measure program impact and optimize decision-making.

Always Be Curious: Skills You've Learned Along The Way:

Technical Skills

• Expertise in program management methodologies, risk mitigation, and execution oversight for complex, high-priority initiatives.
• Proficiency with roadmap management and project tracking tools (e.g., Jira, Asana, Monday.com).
• Data-driven mindset with experience tracking program success, identifying risks, and iterating for improvement.

Interpersonal Skills

• Strong collaboration and stakeholder management skills, with the ability to align cross-functional teams.
• Excellent written and verbal communication skills, with a track record of driving alignment across teams.
• Ability to influence executive teams and senior leaders.

Leadership Competencies

• Demonstrated ability to mentor, coach, and develop team members.
• Experience leading through change and driving organizational initiatives.

Problem-Solving and Decision-Making

• Proactive in identifying challenges and implementing solutions.
• Strong critical thinking and decision-making abilities, especially under pressure.

One Team One Dream: What We Need to Work Together:

Minimum Qualifications

• 10+ years of experience in program management or strategic operations in a growth-stage eCommerce or marketplace company.
• Experience in planning across product and engineering organizations.
• Strong background in driving high-impact, cross-functional programs, especially in a fast-paced environment.
• Proven ability to balance structured execution with flexibility, adapting roadmaps based on insights and market shifts.

Preferred Qualifications

• Experience in the marketplace or live events industries.
• Passion for creating structure in fast-moving, dynamic environments.

What Makes You a Gamechanger: 

• Roadmap Execution: Achieving on-time delivery of high-priority initiatives.
• Risk Mitigation: Reduction in execution risks and implementation of proactive solutions.
• Cross-Functional Alignment: Measured through stakeholder satisfaction and alignment scorecards.
• Process Improvements: Implementation of program management best practices leading to increased efficiency.