Senior Learning Designer Lead, Handshake AI

Handshake • San Francisco, CA

4d

About The Position

As a Senior Learning Designer Lead you will be both the tactical and strategic expert who bridges the gap between our Operations teams and Fellow success. Tactically, you will 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. Strategically, you’ll partner with the team leader to build out a world-class Learning and Training team: Help develop a repeatable process for us to deliver high quality learning experiences with speed Help establish a strong design culture Act as a thought partner for more junior team members on specific projects and with the team leader on particularly thorny design challenges Coach junior team members and enable Operators to increase their learning design and training skills

Requirements

• 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

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

• 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

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
• Remote & Office: 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

What This Job Offers

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