Senior Director, Engineering - TwoTwenty
Leads the TwoTwenty innovation lab’s engineering organization and technical strategy for visual AI assistants, generative creation tools, and editing experiences. The role requires manager-of-managers experience, strong AI or product engineering fluency, and the ability to scale high-performing teams in ambiguous environments.
About the job
Responsibilities
- Drive execution of TwoTwenty’s 1–3 year technical strategy across visual AI assistants, generative AI creation tools, and visual editing experiences.
- Own the investment portfolio across time horizons, balancing near-term shipping velocity with longer-term bets on emerging AI capabilities.
- Set bold OKRs tied to user engagement and adoption; adjust quarterly based on experiment results and market shifts.
- Make final calls on technical trade-offs when speed and rigor are in tension.
- Lead integrated engineering output across mobile, backend, design, and LLM engineering.
- Build partnerships with core Pinterest teams to ship AI features on shared infrastructure at scale.
- Communicate roadmaps and results to senior leadership; secure resources and buy-in for new initiatives.
- Resolve cross-organizational prioritization conflicts.
- Scale the organization by hiring senior technical leaders across mobile, backend, and ML engineering.
- Structure the organization and build succession plans for concurrent product bets.
- Create an environment that attracts and retains product-engineering and AI talent.
- Uphold technical standards for reliability, safety, and scale of agentic AI systems.
Requirements
- Proven experience leading engineering organizations as a manager of managers.
- Track record shipping 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.
- Experience operating in high-ambiguity, greenfield environments and making data-informed pivots.
- Ability to align design, product, and engineering around a shared vision.
- Experience scaling teams while preserving speed and effective culture.
- Hands-on experience with agentic AI architectures, including tool use and multi-step reasoning loops.
- Bachelor’s degree in Computer Science, Engineering, or a related field.
Nice-to-haves
- Experience in visual discovery, search, recommendation systems, or taste graphs.
- Prior startup experience.
Compensation
- Base salary: $329,585–$576,774 USD.
- Eligible for equity.
Skills
Generative AI, LLMs, Machine Learning, Agentic AI, Mobile Engineering, Backend Engineering, Llm Engineering, Recommendation Systems, Search, Okrs
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