Senior Software Engineer, Operator Tooling

ABOUT HANDSHAKE
Keystone AI 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 Keystone AI 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 Keystone AI 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 Keystone AI 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. Keystone AI AI supports all of the frontier AI labs, working on their most complex data at the largest scale.
ABOUT THE ROLE
As a Senior Software Engineer on Operating Tooling, you’ll build internal products and automation that help Keystone AI’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 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.
In this role, you will:
– 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.
DESIRED CAPABILITIES
– 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.
EXTRA CREDIT
– 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).
PERKS
Keystone AI delivers benefits that help you feel supported—and thrive at work and in life.
The below benefits are for full-time US employees.
🎯 Ownership: Equity in a fast-growing company
💰 Financial Wellness: 401(k) match, competitive compensation, financial coaching
🍼 Family Support: Paid parental leave, fertility benefits, parental coaching
💝 Wellbeing: Medical, dental, and vision, mental health support, wellness stipend
📚 Growth: Learning stipend, ongoing development
💻 Remote & Office: Internet, commuting, and free lunch/gym in our SF office
🏝 Time Off: Flexible PTO, 15 holidays + 2 flex days
🤝 Connection: Team outings & referral bonuses
Explore our mission, values, and comprehensive US benefits at joinhandshake.com/careers http://joinhandshake.com/careers.