---
title: 'Director, Learning and Training at Handshake'
canonical: 'https://feeny.ai/job/director-learning-and-training-handshake-san-francisco-j07ra51qgz54'
type: 'job'
last_seen: '2026-11-04'
---

# Director, Learning and Training at Handshake

- **Company:** [Handshake](https://feeny.ai/companies/handshake)
- **Location:** San Francisco, CA
- **Employment:** full-time
- **Work type:** onsite
- **Posted:** 2026-11-02
- **Last confirmed live:** 2026-11-04
- **Apply:** https://jobs.ashbyhq.com/handshake/26ff0af9-54a2-4f94-92f9-351a5a9178dc

## 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

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

## About Handshake

## Company Overview
- **One-liner**: Handshake is the career network for the AI economy, connecting job seekers with internships, full-time roles, freelance gigs, and AI training work through a three-sided marketplace.
- **Entity Type**: Private (Series F; total funding $434M across 6 rounds)
- **Headquarters**: San Francisco, California, USA
- **Founded**: 2014
- **Founders**: Garrett Lord (CEO), Ben Christensen, Scott Ringwelski

## Core Business
- **Primary industry**: Career platform / Job marketplace / AI workforce infrastructure
- **Target customers**: B2C (job seekers, from students to experienced professionals) and B2B (employers including 100% of Fortune 500 and all foundational AI labs; also educational institutions)
- **Mission**: Expand access and improve outcomes for job seekers, helping the workforce stay ahead in the AI economy.

## Products & Services
- **Handshake Core Platform**: A three-sided marketplace connecting 25 million knowledge workers, 1,600+ schools, and 1 million employers. Features dynamic profiles, intelligent job matching, and interactive skill-building.
- **Handshake AI Enterprise**: AI-powered tools for employers and job seekers, including AI-driven matching, safety features, and pay management.
- **AI Trainer Gigs**: Paid, flexible, remote work for individuals to train and evaluate AI models (e.g., AI Evaluation Specialist, up to $40/hr) – no prior AI experience required.
- **Handshake Network**: Community events, career advice, and networking for students, experts, and professionals in AI and other fields.

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed
- **Key Metric**: Total funding $434M (6 rounds); annual revenue $56.5M (LinkedIn estimate)
- **Notable Investors/Partners**: Board includes representatives from General Catalyst, Kleiner Perkins, EQT Ventures, True Ventures, and Niantic. Strategic partners include 100% of the Fortune 500 and foundational AI labs.
- **Growth Signals**: Headcount at 5,272 employees (+708.8% YoY per LinkedIn); 1M+ companies on platform; 25M users; expansion into AI trainer gig economy; new roles in HAI (Handshake AI Enterprise) such as Applied AI Engineer, AI Platform Engineer, and Forward Deployed Engineer.

## Competitive Advantages
- **Network effects**: The only three-sided marketplace linking students, employers, and educational institutions at scale.
- **AI-first positioning**: Deep integration of AI into job matching, skill-building, and new freelance training roles – creating a unique ecosystem for the AI economy.
- **Trusted by elite institutions**: 1,600+ partner schools and every Fortune 500 company provides unparalleled reach into early-career talent.

## Strategic Focus
- **AI economy expansion**: Building the “career network for the AI economy” – expanding beyond college students to all knowledge workers, and adding AI training gigs as a new revenue and engagement stream.
- **Product innovation**: Heavy investment in Handshake AI Enterprise (HAI), including AI matching, safety, and pay infrastructure.
- **Global scaling**: Offices in San Francisco, New York, UK, and Bangalore; operating in 32 countries.

## Why Work Here
- **Culture**: Values include “Students first,” “Leave nothing to chance,” “Own the outcome,” “Invent and reinvent,” and “Olympic pace.” Emphasis on ownership, urgency, and constant evolution.
- **Remote/Hybrid policy**: Many roles are based in San Francisco or New York, but some positions (e.g., Trust & Safety Specialist, Support Specialist) are remote in the US. Recent openings show both office and remote options.
- **Benefits**: Health & wellness support, financial support, time off, modern offices with meals, snacks, and social activities. Strong focus on career growth and learning.
- **Career growth**: Rapid headcount growth suggests ample internal mobility; roles range from engineering (ML, AI, data) to customer success, partnerships, and product management.

## Sources
1. [joinhandshake.com/about](https://joinhandshake.com/about/)
2. [joinhandshake.com/careers](https://joinhandshake.com/careers/)
3. [linkedin.com/company/team-handshake](https://www.linkedin.com/company/team-handshake)
4. [joinhandshake.com](https://joinhandshake.com/)

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