Senior Director, Chief of Staff & Head of Strategy & Operations

We are seeking a strategic, operationally savvy, innovative, results-driven Senior Director who will serve as Chief of Staff to the Chief People Officer (CPO) and lead our Strategy & Operations and Project Management Organization (PMO) teams. In this highly visible role, you will drive key initiatives within and outside of the People team, enable effective decision-making, and oversee the operational rhythm of our entire People organization.

Your mandate will be to set the People Team's operating and planning rhythms, align leaders across Pinterest, and prioritize initiatives that best drive our talent and culture strategy. As a trusted advisor to the CPO, you will foster collaborative partnerships, oversee critical initiatives, and shape the way we work together. Your role is not only to drive operational excellence but also to champion creative thinking, disrupt existing models constructively, and elevate Pinterest as a progressive, best-in-class company for talent and culture. Here, "innovation" means forward-looking, bold, and creative approaches to people, process, and organizational growth.

What you'll do:

Chief of Staff to the Chief People Officer "Office of the CPO"

• Act as trusted advisor and strategic thought partner to effectively establish and maintain the "Office of the CPO".
• In partnership with the Executive Administrative Business Partner, oversee and manage all of the People Team operating cadences to facilitate effective information sharing, knowledge transfer and change management.
• Partner with the CPO as an innovative advisor-applying creativity, data, and design thinking to strategic initiatives, and leveraging storytelling to develop new solutions, measure impact, and celebrate progress.
• Collaborate with colleagues across the People leadership team to define and advance key initiatives with effectiveness and speed.
• Lead and manage the People Team's strategic priorities, ensuring timely execution and alignment across the People team and other functional teams in Pinterest.
• Serve as liaison (point of contact) to other organizations, on behalf of CPO.
• Oversee and actively manage the People Team's annual operating budget.
• Partner with CPO and respective People Team leaders to prepare for board presentations, all company meetings, planning exercises and other functional engagements.
• Partner with internal communications team to manage CPO's internal and external speaking engagements in service to Pinterest and other key stakeholders
• Represent the CPO and People Team in key meetings as needed.

Leader, Strategy & Operations and Project Management

• Lead and oversee the People Strategy & Operations and Project Management teams, ensuring disciplined execution of strategic and operational priorities.
• Facilitate quarterly roadmap reviews and planning discussions on behalf of People organization
• Oversee key operational functions including workforce planning, international expansion, organizational health metrics, budgeting, and process improvement.
• Establish and monitor success metrics for organizational effectiveness, project delivery, and operational excellence.
• Identify and integrate industry-level best practices, continuous improvement and creative innovation in our global processes and operating models.

Strategic Initiatives & Business Partnership

• Lead and manage high-impact, cross-functional initiatives across the People Team and broader business.
• Identify opportunities to enhance organizational effectiveness and employee experience.
• Build strong relationships with People leaders and cross-functional partners to drive execution on strategic priorities.
• Foster a culture of experimentation-piloting new programs, processes, and technologies to advance employee engagement, performance, and belonging.

What Success Looks Like:

• The People Team and CPO's office operate smoothly and are recognized as solutions-oriented, forward-thinking enablers of change.
• Ability to navigate and align complex and ambiguous cross functional issues with peers
• Strong partnership with key stakeholder organizations - Communications, Business Affairs, PTLT, Finance, Legal, IT
• Proactive prioritization and delivery of high-impact work with clear outcomes and metrics for success.
• Effective team management - Building capability of the broader PMO & Strategy and Operations Team; effective capacity management of resources
• The Project Management and Strategy & Operations teams deliver projects on time, on budget, and with high quality.
• The People Team is equipped with operational insights and tools for measurable impact across Pinterest.
  
  

What we're looking for:

• 12+ years of progressive experience in strategy, operations, organizational transformation, or innovation- including time as a Chief of Staff or in a Strategy & Operations leadership role supporting executive leaders in high-growth, global, or tech environments
• Experience managing teams and managers.
• Demonstrated ability to handle confidential information, manage multiple priorities, and execute with a high degree of autonomy.
• Strong analytical, problem-solving, facilitation and communication skills; ability to influence at all levels.
• Creative and innovative mindset, with a strong orientation toward experimentation and growth.Demonstrated ability to connect business strategy to talent and culture priorities, leveraging data and fresh thinking to drive results.
• Passion for invention and improvement; entrepreneurial orientation with a bias toward taking smart risks.
• Strategic agility-proactive in identifying opportunities and mobilizing teams to move quickly and learn boldly.
• Exceptional organizational and program management skills.
• Collaborative, agile, empathetic, resourceful, and solutions-oriented.
  
  

Relocation Statement:

• This position is not eligible for relocation assistance. Visit our PinFlex page to learn more about our working model.
  
  

In-Office Requirement Statement:

• We let the type of work you do guide the collaboration style. That means we're not always working in an office, but we continue to gather for key moments of collaboration and connection.
• This role will need to be in the office for in-person collaboration 1-2 times/month, and therefore can be situated anywhere in the country.

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