Transcarent - Senior Manager, AI and Leadership Enablement
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 • Strategic thinking: Ability to connect workforce development initiatives to business outcomes • Strategic thinking • Facilitation excellence: Skilled at designing and leading engaging workshops, training sessions, and cohort experiences for diverse audiences, including senior leaders • Facilitation excellence • AI-native mindset: Comfortable experimenting with AI tools, staying current on capabilities, and translating technology into practical applications for non-technical audiences • AI-native mindset • Human-centered approach: Deep belief that technology should amplify human potential, not replace human connection • Human-centered approach • Strong communication: Ability to make complex topics accessible and inspire action across all levels of the organization • Strong communication • Data-driven: Comfort with measuring impact and using data to iterate on programs • Data-driven • Collaboration: Proven ability to partner across functions (IT, Communications, HR, business leaders) to drive enterprise initiatives • Collaboration • 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 • As a remote position, the salary range for this role is: • $145,000—$145,000 USD
Responsibilities
• AI Enablement & Workforce Upskilling • 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 • Leadership Development • 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 • L&D Transformation • L&D Transformation • 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
Benefits
• Individual compensation packages are based on a few different factors unique to each candidate, including primary work location and an evaluation of a candidate’s skills, experience, market demands, and internal equity. • Salary is just one component of Transcarent's total package. All regular employees are also eligible for the corporate bonus program or a sales incentive (target included in OTE) as well as stock options. • Our benefits and perks programs include, but are not limited to: • 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
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