Learning Design Lead, Handshake AI

Handshake • San Francisco, CA

1d

About The Position

This role is for someone who wants to 10x themselves.
As a Learning Design Lead, you'll be the tactical expert connecting our Operations teams to Fellow success. Operating in a fast-paced "forward deployed" model, you'll work directly with Operators to rapidly build, ship, and iterate on training solutions - ensuring our Fellows deliver the highest quality AI training data across diverse and evolving projects.
You'll embed with Operations teams launching new projects, scaling existing ones, or tackling quality challenges head-on. You'll need to grasp project requirements quickly, spot training gaps in real-time, and deploy targeted learning solutions within days—not weeks. Your mission: enable Operators to hit their Fellow quality and throughput goals through exceptional training design and rapid execution.

Requirements

• 3+ years of hands-on experience in instructional design and technical training content creation, with a track record of translating complex technical concepts into effective learning experiences
• Thrive in fast-paced, constantly evolving environments where requirements shift and projects launch on tight timelines
• Background in AI or other STEM fields with enough technical depth to understand AI training methodologies and their implications

Nice To Haves

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

Responsibilities

• Move fast on training requests: Turn around project-specific training collateral (playbooks, courses, assessments) within 24-48 hours, and build self-serve resources that help Operators become independent training creators
• Diagnose and fix learning gaps: Dig into learner mistakes, project quality issues, and Operator feedback to pinpoint training gaps—then develop targeted interventions and scalable solutions
• Iterate relentlessly on effectiveness: Track learner quality metrics, completion rates, and satisfaction scores to continuously refine both Fellow training and Operator enablement approaches
• Level up Operators: Train Operators on instructional design fundamentals, feedback techniques, and quality assessment methods so they can better support Fellow development
• Build reusable infrastructure: Create template libraries, content design systems, and frameworks that let Operators independently produce quality training materials while keeping consistency across projects

Benefits

• 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
• Time Off: Flexible PTO, 15 holidays + 2 flex days, winter #ShakeBreak where our whole office closes for a week!
• Connection: Team outings & referral bonuses

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 501-1,000 employees