AI Learning & Development Manager

Chewy, Inc.; Bellevue (WA); On-site; USD 130,000 - 207,000; Full time

Benefits offered by this job

401k

Equity grant

Annual bonus

Unlimited PTO

Paid holidays

Pet insurance discount

Chewy discounts

Job summary

Chewy, Inc. is seeking a Senior AI Learning & Development Manager to lead the Culture & Development efforts within Human Resources.

This role will shape AI-enabled learning, build leadership capabilities for a workforce of humans and AI agents, and deliver personalized experiences aligned with business needs. The candidate will partner with executives to identify skill gaps, design scalable programs, and pilot innovative AI-powered learning tools, ensuring measurable outcomes and responsible AI

Qualifications

• 8+ years in Learning & Development, Leadership Development, Talent Development, Organizational Development, Learning Technology, or related fields with demonstrated experience designing innovative learning solutions.
• Strong understanding of generative AI and emerging AI technologies with application to learning and capability building.
• Proven experience building scalable learning and leadership development programs; knowledge of adult learning and modern learning experience design.
• Ability to challenge traditional approaches, experiment with new solutions, and translate complex concepts into practical, scalable programs.
• Experience evaluating or implementing learning technologies and responsible AI practices.

Responsibilities

• Translate enterprise AI priorities into an actionable learning roadmap building AI literacy and practical skills across populations.
• Partner with business leaders, Technology, and HR to identify skill needs and establish AI proficiency frameworks.
• Design scalable learning experiences that accelerate AI adoption and integrate into existing solutions.
• Reimagine leadership development to prepare leaders to manage teams with humans and AI agents, navigating AI-driven change.
• Lead pilots and experiments with stakeholders; use feedback and outcomes to inform scaling decisions.
• Advise leaders on emerging AI learning opportunities and address governance and data privacy.

Skills

AI literacy

Learning strategy

Stakeholder influence

Leadership development

Experimentation & measurement

Tools

AI-enabled tools

Adaptive learning platforms

Job description

Job Description

Chewy is seeking an Senior AI Learning & Development Manager to join our Culture & Development team within Human Resources. This individual contributor role will play a pivotal part in reimagining how Team Members learn, grow, and lead in an AI-enabled workplace. As AI transforms how work gets done, this individual will challenge traditional approaches to learning and development, introducing innovative, scalable solutions that build AI capabilities, prepare leaders to manage a workforce of humans and AI agents, and deliver personalized learning experiences aligned with evolving business needs. The ideal candidate is a builder, disruptor, and forward-thinking innovator who combines deep learning and development expertise with a strong understanding of emerging AI technologies. Through experimentation, cross-functional partnerships, and a focus on measurable outcomes, this role will help shape the future of learning at Chewy and enable Team Members and leaders to successfully navigate an AI-driven environment. This position reports to the Associate Director, Learning & Development and can be based in any of our main corporate offices in Plantation, FL, Bellevue, WA or Boston, MA.

What You’ll Do

• Translate enterprise AI priorities into an actionable learning roadmap that builds foundational AI literacy, practical application skills, and confidence across Team Member populations
• Partner with business leaders, Technology, and HR to identify emerging skill needs, assess capability gaps, and establish AI proficiency frameworks aligned with business priorities, roles, and leadership levels
• Design scalable learning experiences that accelerate AI adoption and proficiency through hands-on experimentation, real-world applications, peer learning, and self-service resources; integrating ongoing AI skill development into new and existing learning solutions
• Reimagine leadership development to prepare leaders to manage teams where people and AI agents work together, including navigating AI-driven change, redesigning work, making informed decisions, and balancing automation with human judgment and accountability
• Build leaders’ ability to delegate work to AI agents, evaluate AI-generated outputs, establish appropriate human oversight, and guide teams through adoption using immersive learning, simulations, and real-world applications
• Partner with functional leaders to identify critical skills and create personalized, role-based learning pathways that adapt to changing business priorities, roles, and emerging technologies
• Explore and pilot AI-powered learning assistants, coaching tools, and other development experiences that provide relevant guidance, feedback, and resources in the flow of work
• Use AI to accelerate content development, automate learning administration, and improve the accessibility, scalability, and effectiveness of learning; challenging traditional approaches and identifying opportunities to simplify or redesign how learning is developed and delivered
• Lead rapid experiments and pilots with Technology, Learning Technology, and other stakeholders; use Team Member feedback, adoption data, and business outcomes to assess effectiveness and inform decisions about implementation and scale
• Advise HR and business leaders on emerging AI learning opportunities, monitor relevant trends and practices, and establish responsible approaches that address governance and data privacy; measure proficiency, adoption, leadership readiness, productivity, and business impact to improve solutions and scale proven practices

What You’ll Need

• 8+ years of progressive experience in Learning & Development, Leadership Development, Talent Development, Organizational Development, Learning Technology, or related fields, with demonstrated experience designing innovative learning solutions
• Strong understanding of generative AI, AI agents, and emerging AI technologies, with experience applying AI to learning, capability building, workforce transformation, or related business solutions
• Proven experience building, designing, and implementing scalable learning and leadership development programs, with knowledge of adult learning, skills-based development, and modern learning experience design
• Demonstrated ability to challenge traditional approaches, identify emerging opportunities, experiment with new solutions, and translate complex concepts into practical, scalable programs
• Experience evaluating or implementing learning technologies, AI-enabled tools, adaptive learning platforms, or workflow-based learning solutions, with an understanding of responsible AI practices
• Strong ability to influence senior stakeholders, navigate ambiguity, lead complex cross-functional initiatives, and translate strategy into measurable outcomes without direct authority
• Exceptional communication, facilitation, and storytelling skills, with the ability to make emerging AI concepts accessible and actionable for diverse audiences

The base salary range for this role is $129,500 - $207,000.00.

• The specific salary offered to a candidate may be influenced by a variety of factors including but not limited to the candidate’s relevant experience, education, and work location. In addition, this position is eligible for 401k and a new hire and annual equity grant. C08+ positions may also be eligible for annual bonus.

We offer different types of insurance and benefits, such as medical/Rx, vision, dental, life, disability, hospital indemnity, critical illness, and accident. We offer parental leave, family services benefits, backup dependent care, flexible spending accounts, telemedicine, pet adoption reimbursement, employee assistance program, and many discounts including 10% off pet insurance and 20% off at Chewy.com.

Exempt salary team members have unlimited PTO, subject to manager approval. Team members will receive six paid holidays per year. Team members may be eligible for paid sick and family leave in compliance with applicable state and local regulations.

Chewy is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, ancestry, national origin, gender, citizenship, marital status, religion, age, disability, gender identity, results of genetic testing, veteran status, as well as any other legally-protected characteristic. If you have a disability under the Americans with Disabilities Act or similar law, and you need an accommodation during the application process or to perform these job requirements, or if you need a religious accommodation, please contact [e-mail].

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