Senior Software Engineer, Operator Tooling

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.

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.

As a Senior Software Engineer on Operating Tooling, you’ll build internal products and automation that help Handshake’s operators run the business at high quality and speed. This team functions like an embedded/consulting engineering group: you’ll partner directly with operators, learn their workflows deeply, and deliver pragmatic solutions that remove friction, improve quality, and enable new operational capabilities.

This role is highly collaborative and communication-heavy. Success requires strong technical fundamentals plus high EQ—someone who can translate ambiguous operational needs into reliable systems, and iteratively ship improvements that stick.

• Embed with operators to understand processes, pain points, and success metrics; translate them into clear technical requirements and deliverables.

• Architect and build internal tools, automations, and workflows that improve operational throughput, accuracy, and visibility.

• Lead projects end-to-end: discovery, scoping, technical design, implementation, rollout, and iteration.

• Balance speed and quality by making thoughtful tradeoffs, ensuring maintainability, and building with operational reliability in mind.

• Collaborate closely with cross-functional partners (operators, engineering, product) to drive adoption and measurable impact.

• Mentor other engineers and help establish strong engineering practices for an internal-tools environment.

• 5+ years of software engineering experience, with comfort owning systems end-to-end (from requirements through production support).

• Strong communication skills and stakeholder management; able to partner deeply with non-engineering teams and operate with high empathy/EQ.

• Experience building internal tools, workflow systems, or automation for operations-heavy teams (or analogous customer-embedded roles like FDE / solutions engineering).

• Strong engineering judgment: can design scalable systems, pick the right level of abstraction, and avoid over-building.

• Track record of delivering iterative, high-leverage improvements in ambiguous environments.

• Experience with workflow/backlog systems, intake processes, and operational analytics (instrumentation, dashboards, QA).

• Comfort operating in a “player-coach” environment (mix of hands-on building plus lightweight coordination/mentorship as the team grows).

• Background building tooling for knowledge-work operations (e.g., case management, review/approval flows, data quality tooling).