About Pinterest: Millions of people around the world come to our platform to find creative ideas, dream about new possibilities and plan for memories that will last a lifetime. At Pinterest, we’re on a mission to bring everyone the inspiration to create a life they love, and that starts with the people behind the product. Discover a career where you ignite innovation for millions, transform passion into growth opportunities, celebrate each other’s unique experiences and embrace the flexibility to do your best work. Creating a career you love? It’s Possible. At Pinterest, AI isn't just a feature, it's a powerful partner that augments our creativity and amplifies our impact, and we’re looking for candidates who are excited to be a part of that. To get a complete picture of your experience and abilities, we’ll explore your foundational skills and how you collaborate with AI. Through our interview process, what matters most is that you can always explain your approach, showing us not just what you know, but how you think. You can read more about our AI interview philosophy and how we use AI in our recruiting process here. Pinterest is where hundreds of millions of people around the world discover ideas and turn inspiration into action. Our mission is to bring everyone the inspiration to create a life they love, and our values guide how we build, operate, and lead: Put Pinners First, Aim for Extraordinary, Create Belonging, Act as One, and Win or Learn.   Ads brings together Product and Engineering to build the products and systems that power Pinterest’s advertising platform across advertiser and Pinner experiences, enabling sustainable growth while protecting the quality and integrity of the product experience. This organization sits at the intersection of business strategy, scaled engineering systems, and product innovation, making it one of Pinterest’s most business-critical teams. About the Role We are hiring a Chief of Staff to the GM, Ads (Product, Engineering, Data Science) to help scale the organization, sharpen executive decision-making, and drive the operating agenda for this high-impact team. This Chief of Staff (CoS) will act as a senior strategic operator and trusted advisor who connects big-picture priorities with day-to-day execution, serving as a force multiplier for the GM and the broader leadership team.   The role is designed for a leader who can: • Operate as a thought partner to senior executives, with strong business and technical intuition • Build and run scalable operating mechanisms that drive clarity, accountability, and outcomes • Translate complex, ambiguous challenges into structured decisions, owners, and execution plans • Represent the organization in critical cross-functional forums with confidence and credibility across senior technical and business leaders What You’ll Do • Serve as a strategic partner and force multiplier to the GM, Ads and the broader Ads leadership team, helping them stay focused on the most important company and organizational priorities. • Own and continuously refine the executive operating agenda in partnership with leaders and TPMs, including strategic planning, goal setting, quarterly and annual business reviews, leadership offsites, and decision forums. • Lead high-priority, cross-functional initiatives that improve Ad’s execution across Product and Engineering, operating effectiveness, and business impact, stepping in to drive structure, alignment, and momentum where ambiguity is highest. • Translate ambiguous business, technical, and organizational problems into clear frameworks, options, recommendations, and decisions for the VP and leadership team. • Use data, qualitative insight, and organizational “listening” to identify risks, diagnose operating gaps, and proactively surface tradeoffs and implications to leadership. • Build alignment across Engineering, Product, Design, Data Science, Finance, Recruiting, People, and GTM partners, ensuring the Ads organization’s priorities, risks, and resource needs are well understood and integrated into company planning. • Design, implement, and evolve operating mechanisms that improve prioritization, decision quality, communication, and follow-through (for example, leadership cadences, decision logs, roadmap and investment reviews, and accountability trackers). • Support organizational planning and growth, including team structure, headcount and investment tradeoffs, leadership effectiveness, and operating-model evolution as the business and technology landscape changes. • Develop executive-level communications and narratives (for example, decision memos, business reviews, strategy updates, board and ET prep) that clarify strategy, progress, tradeoffs, and decisions for varied audiences. • Represent the Ads organization in critical forums with the Office of the CEO, other functional Chiefs of Staff, and cross-functional leadership groups, modeling the high standards of quality, efficiency, and operational rigor expected of the Office of the CEO and broader executive community. • Act as a culture carrier for Pinterest’s values, helping the organization Put Pinners First, Aim for Extraordinary, Create Belonging, Act as One, and Win or Learn in how it plans, executes, and communicates. • Collaborate with finance teams to manage budgets, optimize spending, and identify opportunities for efficiency and/or investment. • Understand, interface and work closely with recruiting and people orgs to evaluate and nurture healthy, cooperative engineering teams. What We’re Looking For • Minimum 8 years of experience in strategic operations, business operations, program leadership, product operations, technical program management, consulting, finance, or a related role in complex, fast-moving organizations. • Experience operating as a trusted partner to senior executives or leadership teams, with a track record of shaping priorities, driving decisions, and landing complex, cross-functional programs. • Strong strategic judgment and systems thinking, with the ability to connect company and Ads priorities, organizational dynamics, technical realities, and execution constraints into a coherent plan. • Proven ability to lead high-impact initiatives from ambiguous problem definition through measurable outcomes, including establishing clear success metrics, governance, and accountability mechanisms. • Exceptional analytical skills; able to use both quantitative and qualitative data to diagnose issues, frame options, and influence decisions with clear, structured recommendations. • Outstanding executive communication skills, including the ability to craft concise narratives, decision memos, business reviews, and leadership communications for technical and non-technical audiences. • Demonstrated ability to influence without formal authority, build trust quickly, and drive alignment across senior stakeholders with competing priorities and perspectives. • Experience designing and scaling operating mechanisms, planning processes, or organizational systems that improve focus, execution, and cross-functional alignment. • High integrity, discretion, and judgment; comfortable operating with access to sensitive information and navigating nuanced people, organizational, and business situations. • Comfort working at the intersection of technical, product, and business environments; you do not need to be the deepest technical expert, but you must be able to engage credibly with senior engineering and product leaders. • Bachelor's degree or equivalent work experience Preferred Qualifications • Experience partnering directly with Engineering, Product, or other technical executive teams as a Chief of Staff, strategic advisor, or senior TPM/strategic operations leader. • Experience in advertising, marketplace, platform, infrastructure, or other scaled technology environments where monetization, reliability, and user experience must be…