Director of AI Learning & Training (Hands-on)

Handshake; New York (NY); Hybrid; USD 200,000 - 260,000; Full time

Benefits offered by this job

Ownership equity

401(k) match

Parental leave

Medical, dental, and vision

Mental health support

Learning stipend

$500 wellness stipend

Growth and development funding

Remote & Office (SF)

Flexible PTO

Holidays + 2 flex days

Team outings & referral bonuses

Job summary

Handshake AI seeks a seasoned Learning & Training leader to own strategy and results. You will guide a team of learning design leads, step into pods as needed, and set the standard for training quality on frontier AI projects.

You’ll scale across diverse pods, raise data quality for model training, and partner with operations to close training gaps while shaping forward‑looking learning programs.

Qualifications

• 8+ years in enablement or learning design or training.
• 3+ years managing a team of ICs.
• Player-coach mindset with willingness to do hands-on work.
• Operations sense: capacity planning across multiple projects.
• Fluency with AI models and data; ability to reason about model failure.
• Ability to influence up and across leadership.
• Comfort with ambiguity and fast change.

Responsibilities

• Lead and develop the Learning & Training team; coach ICs and grow future leads.
• Stay hands-on by joining pods when needed and building training materials.
• Maintain a high quality standard across pods and systems.
• Plan capacity and decide where to embed, consult, or enable self-service.
• Make ramp time, quality, and project outcomes visible to leadership.
• Collaborate with operations to align training with delivery and gaps.
• Drive strategic L&T programs from vision to shipped implementations.

Job description

Handshake AI seeks a seasoned Learning & Training leader to own strategy and results. You will guide a team of learning design leads, step into pods as needed, and set the standard for training quality on frontier AI projects.

You’ll scale across diverse pods, raise data quality for model training, and partner with operations to close training gaps while shaping forward‑looking learning programs.