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Senior Software Engineer, Annotations

Handshake - San Francisco, CA, United States - In-office - posted 2026-10-02

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Handshake powers 25 million job seekers, 1 million+ employers, and 1,600 educational institutions. The company's AI division (Handshake AI) supports frontier AI labs with high-quality human data for model training and post-training techniques, operating at scale across complex data annotation projects. You will join the Annotations team to build systems that power human data infrastructure for frontier AI companies. This is a high-ownership role working at the intersection of product engineering, distributed systems, and AI data operations. You'll design and build operator tooling that enables teams to create, manage, prioritize, and audit annotation projects at scale. Key responsibilities include: - Building and scaling operator tooling for annotation project lifecycle management (creation, management, prioritization, auditing) - Designing workflows and quality-control systems to improve task accuracy, throughput, and customer outcomes - Developing full-stack features using Python, Node.js/TypeScript, React, PostgreSQL, and backend APIs - Establishing technical direction for complex projects, balancing speed, maintainability, reliability, and operational needs - Partnering with product, design, operations, and data teams to define requirements and ship solutions - Leading projects from concept through production delivery, including rollout, monitoring, and iteration - Mentoring engineers, improving code review quality and architecture discussions, and unblocking the team - Improving engineering processes, testing practices, observability, and operational health You'll work in a fast-moving environment with evolving priorities, partnering closely with cross-functional teams including product, design, data, operations, and engineering. REQUIREMENTS: - 6+ years of software engineering experience building and operating production systems - Strong proficiency in Python, Node.js, TypeScript, React, PostgreSQL, and backend APIs - Experience designing scalable, reliable software and making sound architectural tradeoffs - Track record of owning complex projects from ambiguity through delivery - Strong product judgment and ability to connect technical decisions to customer and business outcomes - Excellent communication skills and ability to work effectively with technical and non-technical partners - Quality mindset: write maintainable code, test thoughtfully, debug deeply, address root causes - Collaborative leadership style with experience mentoring engineers and elevating team practices - Comfort working in high-velocity environments with evolving priorities BONUS: - Experience building workflow, marketplace, operations, or internal-platform software - Familiarity with AI/ML data pipelines, annotation systems, evaluation workflows, or human-in-the-loop products - Experience with distributed teams, expert networks, or high-volume operational processes - Open source contributions or strong record of self-directed technical projects

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