Senior Manager, AI and Leadership Enablement

Role Overview

• Design and execute the enterprise AI enablement strategy, ensuring employees have the skills and confidence to leverage AI tools for productivity, efficiency, and innovation
• Lead the rollout and adoption of enterprise AI tools, partnering with IT, Communications, and business leaders to drive engagement and measurable impact
• Create learning pathways, resources, and just-in-time training that meet employees where they are—from AI-curious to power users
• Develop AI fluency programs that help employees understand when and how to use AI effectively, including prompt engineering, workflow integration, and critical evaluation of AI outputs
• Establish metrics and feedback loops to measure AI adoption, productivity gains, and employee confidence
• Stay current on emerging AI capabilities and continuously iterate on enablement strategies to keep Transcarent at the forefront
• Design, build, and facilitate leadership development programs that meet leaders where they are in their leadership journey—from first-time managers stepping into leadership for the first time to senior leaders driving enterprise strategy
• Upskill leaders on the high-value human work of leadership: building trust, developing talent, having courageous conversations, coaching for performance, and creating environments where people do their best work
• Enable leaders to leverage AI tools effectively so they can spend less time on administrative tasks and more time on the work that matters—leading, developing, and connecting with their teams
• Partner with People Business Partners to identify leadership capability gaps and design targeted interventions
• Facilitate workshops, cohort programs, and experiential learning, and build scalable resources—toolkits, guides, self-directed learning—that support leaders in the moments that matter
• Rethink and transform the Learning & Development function through an AI-first lens
• Leverage AI to create more personalized, efficient, and impactful learning experiences
• Build systems that enable continuous learning, just-in-time support, and knowledge sharing across the organization
• Partner cross-functionally to embed learning and development into the employee journey

Requirements

• 7+ years of experience in Learning & Development, Organizational Development, or a related field, with progressive responsibility
• 3+ years of experience designing and facilitating leadership development programs
• Demonstrated experience with AI enablement, digital transformation, or technology adoption initiatives
• Strong AI fluency—not just understanding what AI can do, but hands-on experience using AI tools to enhance your own work and helping others do the same
• Track record of designing and delivering training programs that drive measurable behavior change
• Experience working in fast-paced, high-growth, or transformation environments

Benefits

• Competitive medical, dental, and vision coverage
• Competitive 401(k) Plan with a generous company match
• Flexible Time Off/Paid Time Off, 13 paid holidays
• Protection Plans including Life Insurance, Disability Insurance, and Supplemental Insurance
• Mental Health and Wellness benefits