Senior Engineering Manager, Quality & Annotations

Handshake; San Francisco (CA); On-site; USD 180,000 - 240,000; Full time

Benefits offered by this job

Equity

401(k) match

Parental leave

Wellness stipend

Learning stipend

Free lunch

Job summary

Handshake seeks a Senior Engineering Manager to own two core teams—Quality and Annotations—leading a combined organization of about 15 engineers. The role sits at the intersection of AI quality tooling and extensible platform infrastructure used daily by operators and fellows.

Based in San Francisco, this in-office position requires a strong track record of growing engineers, strategic planning across teams, and hands-on leadership of senior ICs while guiding cross-team priorities.

Qualifications

• 7+ years engineering experience, including 3+ years managing teams of 8+ and managing managers.
• Background at AI-focused product companies with experience in model quality, data pipelines, and evaluation.
• Strong product engineering instincts for building complex user-facing systems.

Responsibilities

• Lead quality engineering systems to improve AI output reliability, evaluation accuracy, and benchmark performance.
• Own the annotations platform: operator workflows, tasking flows, and data delivery pipelines.
• Build and scale an organization across two domains, developing senior ICs and driving cross-team strategy.

Skills

Engineering leadership

Team management

Product engineering

Prioritization

Stakeholder management

Communication

Job description

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 organization 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).

Requirements

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

Additional Qualifications

• 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

• 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