Senior Software Engineer, Operator Tooling

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 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.

Responsibilities

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

Requirements

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

Nice to have

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)

Benefits

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