Senior Engineering Manager, Quality & Annotations

About Handshake Handshake was founded on a simple belief that everyone deserves a path to a great career, regardless of where they went to school or who they know. Today, we power 25 million job seekers, 1 million+ employers, and 1,600 educational institutions. In 2025, we started Handshake AI and built the fastest-growing AI data business in history. We work directly with frontier AI lab researchers to create evaluations, publish benchmarks, and push the boundary of data. We’ve grown from $0 to ~$1B run rate and pay ~$60M to over 30K individuals every month. Why join Handshake now: - Shape how every career evolves in the AI economy, at global scale, with impact your friends, family and peers can see and feel - Partner hand-in-hand with world-class AI labs, Fortune 500 partners and the world’s top educational institutions - Work together with engineers, scientists, operators, and more from Palantir, Meta, Scale AI, and former YC founders - Build a massive, fast-growing business with billions in revenue About Handshake AI Human data is the core infrastructure to AI advancement. Frontier AI labs currently improve model capabilities with various data-intensive post-training techniques. We believe that data spend for AI training will increase by 3-5x in the next few years and continue for much longer as models take on new domains. Handshake AI supports all of the frontier AI labs, working on their most complex data at the largest scale. ABOUT THE ROLE We're hiring a Senior Engineering Manager to own two of HAI's core engineering teams, Quality and Annotations, leading a combined org of ~15 engineers. This role sits at a rare intersection: one team pushes the frontier of AI quality and evaluation tooling, while the other builds the extensible platform infrastructure that operators and fellows rely on every day. - Lead quality engineering systems that directly improve AI output reliability, evaluation accuracy, and benchmark performance for frontier lab partners - Own the annotations platform: operator workflows, tasking flows, and pipeline infrastructure that powers data delivery - Build and scale an organization across two distinct technical domains, developing senior ICs and driving cross-team technical strategy - Partner with internal stakeholders to prioritize platform investments that unlock other teams to move faster and build on top of shared infrastructure Location: San Francisco, CA. This is an in-office role, 5 days/week (no remote/hybrid) YOU HAVE Must-Haves: - 7+ years of engineering experience, including 3+ years managing engineering teams of 8 or more and experience manager managers. - Background at companies where AI is the core product; you've shipped in environments where model quality, data pipelines, and evaluation rigor are table stakes - Strong product engineering instincts; you can lead teams building complex user-facing systems, not just backend infrastructure - Experience leading teams with meaningfully different technical focuses simultaneously - Track record of developing engineers; you've grown senior ICs, EMs, and leads, not just delivered projects - Strong prioritization and stakeholder management - Clear, direct communicator who can translate between technical complexity and business context What we’re looking for - Engineering leader + builder: 3+ years managing teams, plus 5+ years hands-on engineering experience - Strong people leadership: experience leading senior engineers; managing an EM (or equivalent scope) is a plus - Execution in ambiguity: proven ability to align cross-functionally and deliver in fast-moving, unclear problem spaces - Systems + product mindset: strong platform/distributed systems background, and the ability to turn needs into a clear roadmap, ship iteratively, and measure outcomes Bonus Points: - Familiarity with LLM evaluation, quality pipelines, or applied AI tooling - Experience with annotation or data labeling platforms, tasking systems, or workflow orchestration WE OFFE…