AI Enablement Manager

Docusign • San Francisco, CA

4d • Hybrid

About The Position

Be part of a dynamic team shaping the future of talent at Docusign. As a member of the Tech Learning organization, you’ll help drive a comprehensive strategy to attract, develop, and retain top talent in an AI-forward Docusign. From cultivating future AI champions and leaders to designing engaging AI enablement experiences and strengthening programs that support our people, your work will directly empower individuals and accelerate Docusign’s growth in an AI-Forward world. At the core of this mission is building an AI-forward culture—one that ensures inclusive, equitable access to AI enablement and enables Docusign’s workforce to develop meaningful, real-world AI capabilities. As an AI Enablement Manager, you will play a critical role in scaling Docusign's first AI Academy across functions, sparking curiosity and building applied, ethical AI fluency across the enterprise. This role blends creativity, strategy, and experimentation to design bold, human-centered learning experiences that bring the promise of AI to life in practical and responsible ways. We’re looking for someone who is passionate about learning emerging technologies, can translate complex concepts into compelling experiences, and is comfortable rolling up their sleeves to turn ambitious ideas into reality. This position is an individual contributor role reporting to the Technical Learning Director.

Requirements

• Bachelor’s degree in Technology, Business, Education, or a related field
• 8+ years of experience in Technical Enablement, Talent Strategy, Skill-Based Workforce Transformation, Digital Skills Enablement, or similar roles
• Experience with Human-in-the-Loop (HITL) principles and their application in enterprise environments
• Experience leading complex, cross-functional change and transformation initiatives
• Proven ability to translate technical concepts into measurable business outcomes and communicate effectively with executive, technical, and non-technical stakeholders

Nice To Haves

• Foundational understanding of agentic systems, Artificial Intelligence / Machine Learning (AI/ML), and the Software Development Life Cycle (SDLC)
• Prosci Change Management certification or equivalent
• Experience collaborating with academic institutions, research labs, or external innovation partners

Responsibilities

• Shape the strategic vision for enterprise AI learning, aligning it with Docusign’s principles, priorities, and business objectives
• Translate AI strategy into clear, compelling learning journeys and experiences that drive real-world application
• Design, build, and curate high-impact, role-based AI enablement tracks and content catalogs aligned to business workflows, learner personas, and desired AI capabilities
• Set the vision, design standards, and execution approach for AI enablement—blending creativity, storytelling, and data-driven insights
• Drive AI usage and adoption through structured programs, targeted enablement interventions, and hands-on support
• Design and embed practical, role-based learning into day-to-day workflows grounded in Human-in-the-Loop (HITL) frameworks and proven change management principles
• Partner closely with HR Business Partners and functional leaders to promote AI fluency and sustained adoption across the organization
• Build strong cross-functional relationships with a growing network of AI Champions and AI Multipliers to scale enablement and accelerate AI adoption at both company and functional levels
• Identify and engage strategic partners, curate high-impact content, and translate future-skills strategy into tangible learning outcomes
• Collaborate with cross-functional teams to define, develop, and deploy impact measurement frameworks that assess AI and GenAI contributions to productivity and clearly articulate “what success looks like”
• Serve as a trusted thought partner and advisor to senior leaders driving enterprise AI transformation
• Leverage data, analytics, and continuous feedback to assess learning effectiveness, track adoption, learner outcomes, and capability growth across functions
• Communicate impact and insights clearly, using results to continuously iterate, improve, and scale AI enablement programs

Benefits

• Bonus: Sales personnel are eligible for variable incentive pay dependent on their achievement of pre-established sales goals. Non-Sales roles are eligible for a company bonus plan, which is calculated as a percentage of eligible wages and dependent on company performance.
• Stock: This role is eligible to receive Restricted Stock Units (RSUs).
• Global benefits provide options for the following:
• Paid Time Off: earned time off, as well as paid company holidays based on region
• Paid Parental Leave: take up to six months off with your child after birth, adoption or foster care placement
• Full Health Benefits Plans: options for 100% employer paid and minimum employee contribution health plans from day one of employment
• Retirement Plans: select retirement and pension programs with potential for employer contributions
• Learning and Development: options for coaching, online courses and education reimbursements
• Compassionate Care Leave: paid time off following the loss of a loved one and other life-changing events

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Number of Employees: 5,001-10,000 employees