Staff Software Engineer, TwoTwenty

We're looking for a Staff Software Engineer to lead the technical direction of the backend systems powering Pinterest's AI-driven product experiences — Pinterest Assistant, visual editing and content creation tools and future LLM-based products. You'll design and ship backend systems while architecting the broader platform strategy that enables these experiences to scale across surfaces and teams. This is a hands-on leadership role where you'll move between deep technical execution, system-level architecture and cross-team technical leadership.

What you'll do:

• Define the backend and platform architecture for AI-driven product experiences — visual-chat, AI image generation and editing, and agentic or LLM-based products — partnering with Engineering, Product, ML and UX leaders to shape the technical vision and roadmap.
• Architect end-to-end systems spanning API layers, orchestration, logging, evaluation, storage and safety controls, ensuring solutions scale across multiple products and teams.
• Lead resolution of complex technical challenges — e.g., scaling LLM inference for real-time features, balancing latency vs. quality in AI-generated content, and standardizing backend capabilities for reuse.
• Design and implement production backend systems including API endpoints, orchestration layers, data models, caching strategies and integrations with Pinterest's LLM infrastructure.
• Use AI to accelerate prototyping, evaluation design and code generation, while applying judgment and verification to ensure correctness and quality.
• Create and evolve shared tooling and evaluation frameworks for LLM-based experiences, including offline eval pipelines, A/B testing hooks, quality metrics and observability.
• Guide the design of projects with significant complexity and ambiguity spanning multiple teams — setting technical direction, reviewing critical design docs and driving alignment across cross-functional partners.
• Raise the bar on operational excellence by improving monitoring, alerting, incident response, capacity planning and service health — and mentor engineers to develop stronger ownership habits and grow into technical leaders.

What we’re looking for:

• Bachelor's degree in Computer Science, Engineering or a related field, or equivalent experience.
• Minimum of 6 years of backend software engineering experience with a track record of leading and shipping projects with substantial impact on team-level or org-level goals.
• Experience operating as a technical leader for large, ambiguous, cross-functional initiatives spanning one or more teams.
• Strong Python development skills — you write idiomatic, well-structured, maintainable Python and can confidently navigate and improve large codebases.
• Experience building on top of distributed systems — you've designed, built and operated services at scale, with strong judgment around caching, async processing, data storage tradeoffs, choosing existing database, indexing, and queueing solutions.
• Experience building LLM-powered or ML-backed products in production — you understand model integration, prompt and orchestration strategies, evaluation, latency/cost tradeoffs and operational challenges of AI-backed services.
• Demonstrated ability to use AI to improve speed and quality in your day-to-day workflow, with a clear approach to validating accuracy and quality of AI-assisted work.
• High integrity and ownership: you protect sensitive data, avoid over-reliance on AI and remain accountable for final decisions and deliverables.

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/quarter and therefore can be situated anywhere in the country. 

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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