Senior Learning Designer - Handshake AI

About Handshake AI

Handshake is building the career network for the AI economy. Our three-sided marketplace connects 18 million students and alumni, 1,500+ academic institutions across the U.S. and Europe, and 1 million employers to power how the next generation explores careers, builds skills, and gets hired.

Handshake AI is a human data labeling business that leverages the scale of the largest early career network.We work directly with the world’s leading AI research labs to build a new generation of human data products. From PhDs in physics to undergrads fluent in LLMs, Handshake AI is the trusted partner for domain-specific data and evaluation at scale.

This is a unique opportunity to join a fast-growing team shaping the future of AI through better data, better tools, and better systems—for experts, by experts.

Now’s a great time to join Handshake. Here’s why :

Leading the AI Career Revolution : Be part of the team redefining work in the AI economy for millions worldwide.

Proven Market Demand : Deep employer partnerships across Fortune 500s and the world’s leading AI research labs.

World-Class Team : Leadership from Scale AI, Meta, xAI, Notion, Coinbase, and Palantir, just to name a few.

Capitalized & Scaling : $3.5B valuation from top investors including Kleiner Perkins, True Ventures, Notable Capital, and more.

About the Role

As a Learning Designer - Forward Deployed , you will be the tactical expert who bridges the gap between our Operations teams and Fellow success. You'll operate in a fast-paced "forward deployed" model, working directly with Operators to rapidly create, deploy, and iterate on training solutions that ensure our Fellows can deliver the highest quality AI training data across diverse and evolving projects.

You'll work shoulder-to-shoulder with Operations teams who are launching new projects, scaling existing ones, or troubleshooting quality issues. You'll need to understand project requirements deeply, identify training gaps instantly, and deploy targeted learning solutions within days. Your mission is to enable Operators to achieve their Fellow quality and throughput goals through exceptional training design and rapid deployment.

What you will do

Respond to urgent training requests within 24-48 hours by creating project-specific training collateral (playbooks, courses, assessments) and building self-serve resources that transition Operators from dependency to independent training creation

Analyze learning needs and common errors to identify training gaps through investigation of Fellow mistakes, project quality issues, and Operator feedback to develop targeted interventions and scalable solutions

Analyze performance data and iterate on training effectiveness by tracking Fellow quality metrics, completion rates, and satisfaction scores to continuously refine both Fellow training and Operator enablement strategies

Enable Operators to develop coaching and learning capabilities by training them on instructional design principles, feedback techniques, and quality assessment methods that enhance their ability to support Fellow development

Build scalable training infrastructure including template libraries, content design systems, and reusable frameworks that enable Operators to independently create quality training materials while maintaining consistency across projects

Desired Capabilities

5+ years of deep experience in instructional design and technical training content creation , with demonstrated ability to translate complex technical concepts into effective learning experiences

Proven ability to work in fast-paced, rapidly evolving environments where requirements may change frequently and projects launch with tight deadlines

Background in AI or other STEM disciplines with the technical depth to understand AI training methodologies and their implications

Extra Credit

Enablement experience strongly preferred —experience in customer success, sales enablement, or technical consulting where you've had to rapidly upskill diverse audiences

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 : Stipends for home office setup, internet, commuting, and free lunch / gym in our SF office

Time Off : Flexible PTO, 15 holidays + 2 flex days, winter #ShakeBreak where our whole office closes for a week!

Connection : Team outings & referral bonuses

Explore our mission, values, and comprehensive US benefits at joinhandshake.com / careers .

#LI-MB3

#J-18808-Ljbffr