Senior Software Engineer, Operator Tooling

Cacheflow; San Francisco (CA); Hybrid; USD 170,000 - 260,000; Full time

Benefits offered by this job

Equity in a fast-growing company

401(k) match

Paid parental leave

Medical, dental, and vision

Learning stipend

Flexible PTO

Flexible PTO

Team outings

Job summary

A leading career network company seeks a Senior Software Engineer to build internal products and automations for operational excellence. You will collaborate with operators to understand workflows, lead impactful projects from ideation to deployment, and mentor other engineers. This role demands strong technical fundamentals, excellent communication skills, and a desire to improve operational capabilities. Join a team with strong leadership from renowned tech organizations and enjoy competitive benefits in a thriving work environment.

Qualifications

• Comfort owning systems end-to-end from requirements through production support.
• Able to partner deeply with non-engineering teams and operate with high empathy.
• Experience in operations-heavy environments or customer-embedded roles.

Responsibilities

• Embed with operators to understand processes, pain points, and metrics.
• Architect and build internal tools, automations, and workflows.
• Lead projects end-to-end from discovery to rollout.
• Balance speed and quality with thoughtful tradeoffs.
• Collaborate with cross-functional partners to drive adoption.
• Mentor engineers and help establish engineering practices.

Skills

5+ years of software engineering experience

Strong communication skills

Experience building internal tools

Strong engineering judgment

Track record of delivering iterative improvements

Job description

About Handshake

Handshake is the career network for the AI economy. 20 million knowledge workers, 1,600 educational institutions, 1 million employers (including 100% of the Fortune 50), and every foundational AI lab trust Handshake to power career discovery, hiring, and upskilling, from freelance AI training gigs to first internships to full‑time careers and beyond. This unique value is leading to unparalleled growth; in 2025, we tripled our ARR at scale.

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
• Work hand‑in‑hand with world‑class AI labs, Fortune 500 partners and the world's top educational institutions
• Join a team with leadership from Scale AI, Meta, xAI, Notion, Coinbase, and Palantir, among others
• Build a massive, fast‑growing business with billions in revenue

About the Role

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.

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

Handshake 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.