Senior Learning Designer Lead

• 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
• Collaborate with senior stakeholders (including leaders of Handshake AI) to understand their needs, build trust, and navigate difficulties

• 7+ 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

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

• Equity in a fast-growing company
• 401(k) match, competitive compensation, financial coaching
• Paid parental leave, fertility benefits, parental coaching
• Medical, dental, and vision, mental health support, $500 wellness stipend
• $2,000 learning stipend, ongoing development
• Internet, commuting, and free lunch/gym in our SF office
• Flexible PTO, 15 holidays + 2 flex days, winter #ShakeBreak where our whole office closes for a week
• Team outings & referral bonuses