Senior Manager, AI and Leadership Enablement

About This Role:

The Senior Manager, AI and Leadership Enablement is responsible for enabling and developing our employees to succeed, grow, and lead. This role will ensure our workforce has the skills and tools to do their best work—equipping them with AI fluency to drive productivity and efficiency, while building leadership capabilities that help our people thrive and advance in their careers.

You will lead our enterprise AI enablement efforts, helping employees work smarter and focus on what matters most. You will also design and deliver leadership development programs that grow our next generation of leaders and strengthen the capabilities of those already leading teams.

This is an opportunity to shape how Transcarent invests in its people—building a culture of continuous learning where employees feel empowered, supported, and ready to deliver exceptional outcomes for our Members.

What You'll Do:

• 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

What We're Looking For:

• 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

• Strategic thinking: Ability to connect workforce development initiatives to business outcomes
• Facilitation excellence: Skilled at designing and leading engaging workshops, training sessions, and cohort experiences for diverse audiences, including senior leaders
• AI-native mindset: Comfortable experimenting with AI tools, staying current on capabilities, and translating technology into practical applications for non-technical audiences
• Human-centered approach: Deep belief that technology should amplify human potential, not replace human connection
• Strong communication: Ability to make complex topics accessible and inspire action across all levels of the organization
• Data-driven: Comfort with measuring impact and using data to iterate on programs
• Collaboration: Proven ability to partner across functions (IT, Communications, HR, business leaders) to drive enterprise initiatives

• Experience in healthcare, technology, or high-growth startup environments
• Familiarity with enterprise AI tools (e.g., Microsoft Copilot or similar)
• Coaching certification or executive coaching experience
• Experience with instructional design and adult learning principles
• Background in change management methodologies