Senior Learning Design Lead

About Handshake

Handshake is the career network for the AI economy. 20 million knowledge workers, 1,600 educational institutions, 1 million employers (including 100% of the Fortune 50), and every foundational AI lab trust Handshake to power career discovery, hiring, and upskilling - from freelance AI training gigs to first internships to full-time careers and beyond. This unique value is leading to unparalleled growth; in 2025, we tripled our ARR at scale.

Why join Handshake now:

• Shape how every career evolves in the AI economy, at global scale, with impact your friends, family, and peers can see and feel
• Work hand-in-hand with world-class AI labs, Fortune 500 partners, and the world's top educational institutions
• Join a team with leadership from Scale AI, Meta, xAI, Notion, Coinbase, and Palantir, among others
• Build a massive, fast-growing business with billions in revenue

The Role

As a Senior Learning Design Lead , you'll make quality compound across Handshake AI's portfolio of data projects. Reporting to the Head of Learning & Training, you'll work in two modes: embedded directly with Operations teams on fast launch cycles, and building the systems that carry quality judgment from one project to the next.

Beyond individual projects, you'll bring a strong point of view to our design culture - pressure testing work, raising the bar, and acting as a thought partner to teammates on thorny design challenges and to the team lead on how our systems and standards should evolve. You'll also coach designers and Operators to grow their learning design and training craft, helping the whole team get better over time. This role is central to how the world's leading AI labs get the high-quality data they depend on.

• Forward Deploy: Embed with Operations teams launching or scaling live projects, shipping targeted training materials within 24-48 hours to hit Fellow quality and throughput goals
• Learning Design: Design and deploy playbooks, courses, and assessments that translate complex data annotation requirements into learner-ready experiences
• Knowledge Transfer: Work with research and project teams to apply insights from individual projects across similar data types at scale
• Design Review: Strengthen team quality through structured critique that holds a consistent bar across all learning deliverables
• Operator Enablement: Train Operators on instructional design principles, feedback techniques, and quality assessment methods to build lasting coaching capabilities
• Cross-Functional Alignment: Drive quality initiatives that align data science, operations, and product partners around a shared quality bar - without formal authority

You Have

• 7+ years in instructional design or technical training, with a track record of translating complex technical concepts into effective learning
• Practical AI fluency - you use these tools daily and can diagnose and redirect AI-generated content with pedagogical precision
• Proven ability to ship training materials on tight deadlines in fast-paced environments where requirements change frequently
• Experience driving quality standards across cross-functional teams without formal authority
• Strong analytical instincts - you track quality metrics and completion rates to identify gaps and iterate on programs

Bonus Points:

• Background in sales enablement or technical consulting, where you've rapidly upskilled diverse audiences on complex subject matter
• Experience in AI/ML data operations or human data labeling workflows
• Track record of building design review systems or quality rubrics that scale across teams

We Offer

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

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