Director, Learning and Training

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

About Handshake AI

Handshake AI is a human data business built on the largest early-career network in the world: about 18 million students and over a million employers. Frontier AI labs come to us when they need domain experts at scale, from PhD physicists evaluating reasoning to AI-native undergrads giving nuanced feedback on model outputs. Learning & Training (L&T) makes that expertise usable. We get fellows project-ready fast, then develop them into high-quality AI training talent. We teach them how models work, how to spot hallucinations, how to give structured feedback that improves a model, and how to think about alignment and safety. The team runs a forward-deployed model. Learning designers embed in project pods alongside operations and turn technical specs into training promptly: playbooks, courses, interactive tools, and targeted coaching on specific errors. They also build team-wide systems like assessment, analytics, and design agents.

The Role

You’ll lead the Learning & Training team, owning the function’s strateg and its results: how fast fellows ramp, and how good their work is once they do. This is a player-coach role. You’ll lead a team of learning design leads and also roll up your sleeves: step into a pod when a new lab spec lands, build a course or coaching plan yourself, and set the bar by example as well as by review. You’ll scale the forward-deployed model across more pods and project types, and deliver training that gets fellows ramped faster and raises the quality of the data we ship to labs. This role sits closer to model development than almost any learning job. The training you shape determines the quality of the data frontier labs use to make models smarter, safer, and better aligned.

What You’ll Do

• Lead and develop the team. Coach ICs who each go deeper than you in their own domain. Grow future leads from within.
• Stay hands-on. Jump into pods when demand spikes or a project is new. Build training, review fellow errors, and model the standard you expect.
• Hold the quality bar high. Keep design standard and systems in use across very different pods, so quality doesn't depend on any one person being in the room.
• Scale the forward-deployed model. Plan capacity so the team is on the most important projects while system work still gets time. Decide where to embed, where to consult, and where pods can self-serve.
• Make impact visible. Turn ramp time, fellow quality, and project outcomes into a story that operations and leadership trust.
• Partner across operations. Work with fellow experience, quality, and delivery so training gaps are caught before they become quality issues.
• Drive strategic programs. Turn a vision for L&T into programs that ship and get adopted.

What We’re Looking For

• 8+ years in enablement, learning design, or training, including 3+ years managing a team of experienced individual contributors.
• A player-coach mindset. You’re willing to hustle as an IC and still build things yourself when the work calls for it.
• Operations sense. You’ve managed capacity across many concurrent projects where training ships in days, not quarters.
• Fluency with AI models and data. You use models daily, can reason about how they fail, and understand how data quality shapes model behavior. Coding expertise is not required.
• A track record of defining and holding a quality bar through standards, review, and coaching.
• Skill at influencing up and across. You can make the case for a function to operations leaders who measure everything.
• Comfort with ambiguity and fast change.

Nice‑to‑haves

• Background in data annotation and model evaluation.
• Experience training domain experts (PhDs, engineers, professionals) in addition to general audiences.
• Experience building learning analytics or skills assessment systems.

What This Role Is Not

• A traditional L&D or corporate training role. There’s no LMS rollout or annual curriculum calendar. You build tools to break any blockers.
• A domain expert for every pod. Your designers hold the domain depth. You bring judgment, the standard, and a willingness to dig in wherever you’re needed.
• A hands-off executive. You’ll lead the team and still do some of the work yourself.

If you want to lead a sharp team, stay close to the craft, and shape how the next generation of AI models gets trained, we’d love to hear from you.

Perks

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

Compensation Range: $200K - $260K