Director, Learning and Training

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

Must-haves

• 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

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