Sr. Director, Engineering - TwoTwenty (Innovation Lab)

TwoTwenty is Pinterest's innovation lab, building visual-first AI products — assistants, Gen-AI creation tools, and editing experiences — with startup speed at Pinterest scale. We're looking for a Senior Director of Engineering to lead a team of 10 (7 direct reports across ML engineering, software engineering, data science, and product management), own the technical strategy for TwoTwenty's AI product portfolio, and scale the org from scrappy to enduring without losing what makes it fast.

This role reports to the VP of Product Management, Core, and partners closely with Pinterest's Core Product & Engineering, Advanced Technologies Group, and Trust & Safety teams to ship AI features that reach hundreds of millions of Pinners.

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.

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