Senior Engineering Manager (Quality & Annotations)

Join Handshake, a leading AI company, as a Senior Engineering Manager. In this role, you will lead two core engineering teams, Quality and Annotations, and drive cross-team technical strategy. You will have a direct impact on AI output reliability, evaluation accuracy, and benchmark performance. The position offers a comprehensive benefits package, including health insurance, fertility and family forming support, mental health resources, life and disability insurance, a 401k match, equity, financial management services, learning and development opportunities, parental leave, flexible time off, a sabbatical, and volunteer time off.

• Lead and manage two core engineering teams focused on quality engineering systems and annotations platform.
• Develop and implement strategies to improve AI output reliability, evaluation accuracy, and benchmark performance.
• Build and scale the organization across two distinct technical domains, developing senior individual contributors and driving cross-team technical strategy.
• Track record of developing engineers; you've grown senior ICs, EMs, and leads, not just delivered projects
• Strong product engineering instincts; you can lead teams building complex user-facing systems, not just backend infrastructure
• Strong prioritization and stakeholder management
• 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
• 7+ years of engineering experience, including 3+ years managing engineering teams of 8 or more and experience manager managers
• Experience leading teams with meaningfully different technical focuses simultaneously
• Clear, direct communicator who can translate between technical complexity and business context
• Strong people leadership: experience leading senior engineers; managing an EM (or equivalent scope) is a plus
• Systems + product mindset: strong platform/distributed systems background, and the ability to turn needs into a clear roadmap, ship iteratively, and measure outcomes
• Engineering leader + builder: 3+ years managing teams, plus 5+ years hands-on engineering experience
• Execution in ambiguity: proven ability to align cross-functionally and deliver in fast-moving, unclear problem spaces
• Experience with annotation or data labeling platforms, tasking systems, or workflow orchestration
• Familiarity with LLM evaluation, quality pipelines, or applied AI tooling