EdTech Jobs
Handshake

Engineering Manager, AI Evaluation

Handshake
🇺🇸In-Person - San Francisco, CA22h ago
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Role Snapshot

Senior Engineering Manager leading two core engineering teams (Quality and Annotations) with ~15 engineers at Handshake AI, responsible for building AI quality evaluation systems and annotation platform infrastructure that directly impacts frontier AI lab partners.

Key Responsibilities: Lead quality engineering systems for AI output reliability and evaluation accuracy; own annotations platform including operator workflows, tasking flows, and pipeline infrastructure; build and scale organization across two technical domains while partnering with internal stakeholders on platform investments.
Skills & Tools: Strong product engineering instincts for complex user-facing systems; ability to manage teams with diverse technical focuses; experience with AI quality pipelines, data evaluation rigor, and shipping in AI-first environments; bonus skills in LLM evaluation, annotation platforms, and workflow orchestration.
Qualifications: 7+ years of engineering experience including 3+ years managing engineering teams of 8+ people with experience managing managers; background at companies where AI is core product with demonstrated expertise in model quality, data pipelines, and evaluation rigor.
Location: In-Person - San Francisco, CA
Compensation: Not provided by employer. Typical compensation for this role is $280,000 – $380,000/year based on title, seniority, and location.

Job Description

About Handshake

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.

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

  • 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 Handshake 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. Handshake AI supports all of the frontier AI labs, working on their most complex data at the largest scale.

About the Role

We're hiring an Engineering Manager to own our Quality team. The team builds the systems that define, select, and enforce quality standards across the data and evaluations we deliver to leading AI labs.

This team works on infrastructure that evaluates complex outputs submitted by fellows, such as coding tasks designed to challenge advanced AI models. These quality checks run throughout the production process: providing real-time feedback to fellows, supporting internal operators, and validating outputs before they reach customers.

Location: San Francisco, CA. This is an in-office role, 5 days/week (no remote/hybrid)

You Have

Must-Haves:

  • 7+ years of engineering experience, including 3+ years managing engineering teams of 8 or more and experience manager managers.

  • 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

  • Strong product engineering instincts; you can lead teams building complex user-facing systems, not just backend infrastructure

  • Experience leading teams with meaningfully different technical focuses simultaneously

  • Track record of developing engineers; you've grown senior ICs, EMs, and leads, not just delivered projects

  • Strong prioritization and stakeholder management

  • Clear, direct communicator who can translate between technical complexity and business context

What we’re looking for

  • Engineering leader + builder: 3+ years managing teams, plus 5+ years hands-on engineering experience

  • Strong people leadership: experience leading senior engineers; managing an EM (or equivalent scope) is a plus

  • Execution in ambiguity: proven ability to align cross-functionally and deliver in fast-moving, unclear problem spaces

  • Systems + product mindset: strong platform/distributed systems background, and the ability to turn needs into a clear roadmap, ship iteratively, and measure outcomes

Bonus Points:

  • Familiarity with LLM evaluation, quality pipelines, or applied AI tooling

  • Experience with annotation or data labeling platforms, tasking systems, or workflow orchestration

We Offer

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, $500 wellness stipend

📚 Growth: $2,000 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.