Full-Time
Senior Manager
AI and Leadership Enablement
Transcarent
501-1,000 employees
On-demand medical access and delivery
Compensation Overview
$145k/yr
Remote in USA
Remote
 Training |
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- Seven or more years of experience in Learning & Development, Organizational Development, or a related field, with progressive responsibility.
- Three or more years of experience designing and facilitating leadership development programs.
- Demonstrated experience with artificial intelligence enablement, digital transformation, or technology adoption initiatives.
- Strong artificial intelligence fluency, including 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: 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.
- 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.
- 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.
Transcarent runs a digital health platform for individuals, families, and employers, offering 24/7 access to doctors via chat, personalized care guidance from health concierges, and doorstep medication delivery. Members join through employer plans or directly, then use the app or website to chat with doctors within 60 seconds, receive tailored care help, and order medicines to be shipped to their home. It differentiates itself by pairing immediate medical access with concierge support and cost transparency, supported by subscription options for employers and premium plans for individuals. The goal is to make healthcare less confusing, simpler to navigate, and more affordable by delivering easy access to care, trusted guidance, and clear information.
Company Size
501-1,000
Company Stage
Series D
Total Funding
$424M
Headquarters
San Francisco, California
Founded
2020
Simplify's Take
What believers are saying
- Transcarent raised $126M Series D and prior $200M Series C, fueling growth.
- $621M Accolade acquisition serves 1,400+ employer clients with GenAI specialty care.
- FDA eases AI device regulations in 2026, boosting Transcarent's virtual care tech.
What critics are saying
- 98point6 integration fails, disrupting services and eroding trust within 6-12 months.
- Amazon Clinic free virtual care captures market share from Transcarent subscriptions in 3-6 months.
- Bluespine AI falsely flags claims, sparking lawsuits and client churn in 6-12 months.
What makes Transcarent unique
- Transcarent integrates AI-powered payment integrity via Bluespine partnership to combat $300B healthcare fraud.
- Transcarent acquires 98point6 for AI virtual care and Accolade for $621M health advocacy expansion.
- Transcarent delivers 24/7 doctor chats in 60 seconds plus medication delivery for self-insured employers.
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Benefits
Health Insurance
Dental Insurance
Vision Insurance
Life Insurance
Disability Insurance
401(k) Company Match
Unlimited Paid Time Off
Paid Vacation
Mental Health Support
Wellness Program
Growth & Insights and Company News
6 month growth
↓ -2%1 year growth
↓ -4%2 year growth
↓ -6%Transcarent has launched a payment integrity category in its Experience Store through a partnership with Bluespine, an AI-driven health technology company. The initiative aims to help self-insured employers detect overbilling and reduce waste in healthcare spending. Fraud, waste and abuse account for an estimated 3% to 10% of total US healthcare spending, representing over $300 billion annually. Unlike traditional audits that review limited claim samples, Bluespine analyses 100% of medical and pharmacy claims using AI to identify overpayments, policy violations and billing errors. The platform supports both prepayment review and post-payment recovery, validating claims against employers' specific plan documents, coverage exclusions and negotiated rates. Every identified issue is documented with clear evidence tied to plan language or billing guidelines, enabling streamlined recovery without disrupting member experience.
Transcarent, the One Place for Health and Care, and Accolade (NASDAQ:ACCD), a leader in health advocacy, expert medical opinions, and primary care, an
Transcarent, a San Francisco, CA-based healthcare platform provider, raised $126m in Series D funding
Transcarent, a health and care experience company that makes it easy for people to access high-quality, affordable care announced plans to acquire the
Transcarent, a Palo Alto, Calif.-based health and care experience company, raised $200m in Series C funding