Senior Manager, AI and Leadership Enablement

Transcarent is Hiring for a Full Time Senior Manager, AI & Leadership Enablement. This position is Remote. Applicants with experience in strong leadership development programs, led large group of trainings on leadership skills, passionate about AI, high fluency in AI, and taking AI forward approach & perspective to help us become more efficient in our work, this position is for you! 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: 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 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: Required Experience: 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 Skills & Competencies 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 Preferred Qualifications: 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 Who we are Transcarent is the One Place for Health and Careᵀᴹ, bringing medical, pharmacy, and point solutions together with the WayFinding ᵀᴹ experience, the first and only generative AI-powered health and care platform for health consumers. Our WayFinding experience, paired with transparent and consumer-driven pharmacy care, 2nd.MD expert medical opinions, and virtual primary care, works seamlessly with comprehensive Care Experiences – Cancer Care, Surgery Care, and Weight Health – to support people with all of their health needs, simple or serious. More than 1,700 employers and health plans rely on us to provide information, guidance, and care, empowering health consumers with more choice, an experience they love, access to higher-quality care, and lower costs for 21 million Members. For more information, visit transcarent.com , and follow us on LinkedIn . At Transcarent, our values guide everything we do: People First: We prioritize our Members, clients, and each other in every decision Care: Every decision starts with improving health and care for our Members Resilience: We push boundaries and take the uncharted path to change an industry Results: We take ownership, solve with speed, and deliver for our people and each other Humble and Human: We lead with humility, bring fun to tough moments, and go further together Total Rewards 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 Transcarent is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. If you are a person with a disability and require assistance during the application process, please don’t hesitate to reach out! Research shows that candidates from underrepresented backgrounds often don’t apply unless they meet 100% of the job criteria. While we have worked to consolidate the minimum qualifications for each role, we aren’t looking for someone who checks each box on a page; we’re looking for active learners and people who care about disrupting the current health and care with their unique experiences.