Senior Engineering Manager, Quality & Annotations

Edtech.com's Summary

Handshake is hiring a Senior Engineering Manager, Quality & Annotations to lead two core engineering teams focused on AI quality evaluation and annotations platform infrastructure. The role involves managing around 15 engineers, driving technical strategy, improving AI output reliability, and scaling operator workflows and data delivery systems.

Highlights

Lead engineering teams focused on AI quality systems and annotations platform.
Manage a combined organization of approximately 15 engineers across different technical domains.
Develop senior individual contributors and managers, fostering leadership growth.
Prioritize and partner with stakeholders to enhance shared platform infrastructure.
Require 7+ years engineering experience, including 3+ years managing teams of 8 or more.
Experience in AI-centric companies with strong background in model quality, data pipelines, and evaluation.
Strong product engineering instincts to lead both user-facing systems and backend infrastructure.
Clear communication skills to translate technical complexity into business context.
Bonus for experience with LLM evaluation, AI tooling, and annotation or tasking platforms.
Compensation includes competitive salary, equity, 401(k) match, paid parental leave, medical and wellness benefits, learning stipends, and flexible PTO.

Senior Engineering Manager, Quality & Annotations Full 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. Weâve 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 worldâs 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 a Senior Engineering Manager to own two of HAI's core engineering teams, Quality and Annotations, leading a combined org of ~15 engineers. This role sits at a rare intersection: one team pushes the frontier of AI quality and evaluation tooling, while the other builds the extensible platform infrastructure that operators and fellows rely on every day.

Lead quality engineering systems that directly improve AI output reliability, evaluation accuracy, and benchmark performance for frontier lab partners
Own the annotations platform: operator workflows, tasking flows, and pipeline infrastructure that powers data delivery
Build and scale an organization across two distinct technical domains, developing senior ICs and driving cross-team technical strategy
Partner with internal stakeholders to prioritize platform investments that unlock other teams to move faster and build on top of shared infrastructure

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 weâre 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.

ð¯ Ownership: Equity in a fast-growing company

ð° Financial Wellness: 401(k) match, competitive compensation, financial coaching

ð¼ Family Support: Paid parental leave, fertility benefits, parental coaching

ð Wellbeing: Medical, dental, and vision, mental health support, $500 wellness stipend

ð Growth: $2,000 learning stipend, ongoing development

ð» Remote & Office: Internet, commuting, and free lunch/gym in our SF office

ð Time Off: Flexible PTO, 15 holidays + 2 flex days

ð¤ Connection: Team outings & referral bonuses

Explore our mission, values, and comprehensive US benefits at joinhandshake.com/careers .

Original Job Description