Senior Manager, AI and Leadership Enablement

🕒 February 14

🇺🇸 United States – Remote

💵 $145k / year

⏰ Full Time

🟠 Senior

🤖 Artificial Intelligence

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Transcarent

WebsiteLinkedInAll Job Openings

201 - 500 employees

Founded 2020

⚕️ Healthcare Insurance

🤖 Artificial Intelligence

💰 $200M Series C on 2022-01

Healthcare Insurance • Health • Artificial Intelligence

Transcarent is a healthcare solutions company that simplifies access to high-quality, affordable health and care for individuals and employers. They provide comprehensive support across the healthcare journey, including navigation, clinical guidance, and on-demand care delivery through their dedicated team of Health Guides and local providers. Utilizing advanced technology and generative AI, Transcarent enhances member experiences while striving to improve health outcomes and reduce costs associated with care.

📋 Description

• 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