Sr. Director, Engineering - TwoTwenty (Innovation Lab)

What you'll do: Drive execution of TwoTwenty's 1–3 year technical strategy across visual AI assistants, gen-AI creation tools, and visual editing experiences Own the investment portfolio across time horizons — balance near-term shipping velocity against longer-term bets on emerging AI capability Set bold OKRs tied to Pinner engagement and adoption; adjust quarterly based on experiment results and market shifts Make the final call on technical trade-offs when speed and rigor are in tension Serve as the single engineering leader accountable for TwoTwenty's integrated output — aligning mobile, backend, design, and LLM engineering under one product vision Build strategic partnerships with core Pinterest teams (Closeup, Search, Assistant) to ship AI features at Pinterest scale on shared infrastructure Communicate roadmap and results to senior leadership and executives; secure resources and buy-in for new bets Resolve cross-org prioritization conflicts so TwoTwenty's rapid iteration cadence doesn't create friction with platform teams Scale TwoTwenty from a small, scrappy team to a high-performing org while preserving its speed and culture — hire senior technical leaders (Staff/Principal) across mobile, backend, and ML Structure the org and build succession plans that support multiple concurrent product bets with no single point of failure Create an environment that attracts and retains top product-engineering and AI talent, with equitable growth paths across disciplines Set and uphold the technical bar for reliability, safety, and scale of agentic AI systems across Pinterest's multi-billion-Pin ecosystem What we're looking for: Proven track record leading engineering orgs (manager-of-managers) that shipped consumer-facing AI/ML products at scale Deep technical fluency in at least one of: LLM/generative AI systems, mobile product engineering, or AI-driven experiences — enough to make strategic technical calls and earn credibility with Staff+ engineers Experience operating in high-ambiguity, greenfield environments — comfortable making bets without perfect data and pivoting fast on results Demonstrated ability to align design, product, and engineering around a shared vision and ship integrated experiences Experience scaling a team while protecting speed — knows when to add process and when to guard scrappiness Relevant domain experience within visual discovery, search, recommendation systems, and/or taste graphs preferred Hands-on experience with agentic AI architectures (tool-use, multi-step reasoning loops) Prior experience in a startup environment highly preferred Bachelor’s Degree in Computer Science, Engineering, or related field In-Office Requirement Statement: We recognize that the ideal environment for work is situational and may differ across departments. What this looks like day-to-day can vary based on the needs of each organization or role. This role will need to be in the office for in-person collaboration 1-2 times per month and therefore needs to be in a commutable distance from one of the following offices: Palo Alto, San Francisco, or Seattle offices. Relocation Statement: This position is not eligible for relocation assistance. Visit our PinFlex page to learn more about our working model. #LI-HYBRID #LI-RR4 At Pinterest we believe the workplace should be equitable, inclusive, and inspiring for every employee. In an effort to provide greater transparency, we are sharing the base salary range for this position. The position is also eligible for equity. Final salary is based on a number of factors including location, travel, relevant prior experience, or particular skills and expertise. Information regarding the culture at Pinterest and benefits available for this position can be found here . US based applicants only $329,585 — $576,774 USD Our Commitment to Inclusion: Pinterest is an equal opportunity employer and makes employment decisions on the basis of merit. We want to have the best qualified people in every job. All qualified applicants will receive consideration for employment without regard to race, color, ancestry, national origin, religion or religious creed, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender, gender identity, gender expression, age, marital status, status as a protected veteran, physical or mental disability, medical condition, genetic information or characteristics (or those of a family member) or any other consideration made unlawful by applicable federal, state or local laws. We also consider qualified applicants regardless of criminal histories, consistent with legal