Director, Learning and Training
Handshake · San Francisco, CA · onsite
USD 200,000 to 260,000 per year
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. Each learning designer leads a project pod, embedded with operations, and turns new lab specs into training within days: playbooks, courses, interactive tools, and targeted coaching on specific errors. About 80% of the team's time is in pods and 20% on team-wide systems like assessment, analytics, and rubrics. L&T is a platform pods use, not a team they wait for.
ABOUT THE ROLE
You'll lead the Learning & Training as it joins Central Ops alongside fellow experience and quality, reporting to the VP of Central Ops. You own the function's strategy, its team, and its results: how fast Fellows are trained and ramp up, and the quality of their work
This is a player-coach role. You'll lead four senior learning designers and also roll up your sleeves: step into a pod when a new lab spec lands, build a course or a coaching plan yourself, and set the bar by example as well as by review. As the team grows, the balance shifts toward leading, but you'll never be far from the work.
You'll inherit a working model and a strong team. The job is to lead them, scale the model across more pods and project types, and make L&T's impact clear to operations and leadership.
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.
IN THIS ROLE, YOU WILL:
- Lead and develop the team. Coach senior 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. Keep a written design standard 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 Central Ops. 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.
- Hire. Grow the team as demand grows, including hard-to-find technical and safety expertise.
YOU HAVE
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 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 a function that is still taking shape.
Nice-to-haves:
- Background in human data, data annotation, RLHF, or model evaluation.
- Experience training domain experts (PhDs, engineers, professionals) rather than general audiences.
- Familiarity with technical or coding training, or with AI safety evaluation.
- Experience building learning analytics or skills assessment systems.
- Hands-on comfort with SQL, scripting, or evaluation tooling.
What this role is not
- A traditional L&D or corporate training role. There's no LMS rollout or annual curriculum calendar.
- 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