Head of Learning Jobs
Head of Learning jobs are open across corporate enterprises, healthcare, technology, and nonprofit sectors, from manager and director to VP and chief learning officer, with specializations in instructional design, leadership development, and learning technology. Find a role that fits below and apply directly.
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We’re building a world of health around every individual — shaping a more connected, convenient and compassionate health experience. At CVS Health®, you’ll be surrounded by passionate colleagues who care deeply, innovate with purpose, hold ourselves accountable and prioritize safety and quality in everything we do. Join us and be part of something bigger – helping to simplify health care one person, one family and one community at a time.
Position Summary
The Executive Director, Head of Learning Strategy, Design & Learner Experience is a member of the Learning & Development Leadership Team responsible for shaping and executing the enterprise learning strategy and creating modern, high-impact learning experiences that build workforce capability and support business performance.
This leader oversees learning strategy, enterprise learning design, curriculum and content, learner experience, learning technology strategy, AI-enabled learning, analytics, and the Learning Design Center of Excellence. In close partnership with DDAT/HR Technology, the role translates L&D priorities and learner needs into the technology capabilities and digital experiences required to enable them.
The role sets enterprise standards and drives innovation across the learning ecosystem, improving quality, speed, scalability, accessibility, learner experience, and business impact while simplifying how learning is designed and delivered.
Key Responsibilities
Enterprise Learning Strategy & Governance
- Define and execute the enterprise learning strategy and multi-year roadmap aligned with business, talent, skills, and workforce priorities.
- Establish enterprise standards and governance for learning design, curriculum architecture, content, accessibility, learner experience, and measurement.
- Translate business and workforce capability needs into scalable learning strategies and solutions.
- Serve as a strategic advisor to senior leaders on learning, skills, AI, and workforce capability trends.
Learning Design & Learner Experience
- Lead the Learning Design Center of Excellence and end-to-end design and development of enterprise learning experiences across digital, virtual, instructor-led, multimedia, performance support, immersive, and AI-enabled modalities.
- Establish modern learning design and learner experience principles grounded in learning science, accessibility, user experience, and measurable performance outcomes.
- Drive consistency, quality, reuse, modularity, and scalability across enterprise curricula and content.
- Lead the strategy and learner experience for Classroom of the Future, partnering with DDAT on enabling technology products and capabilities.
- Oversee learning demand, prioritization, capacity, and delivery to balance strategic initiatives with ongoing business and regulatory needs.
Learning Technology & Digital Enablement
- Serve as L&D's strategic partner to DDAT/HR Technology, translating learning and learner experience requirements into technology capabilities and roadmaps.
- Partner on the strategy, governance, selection, optimization, and evolution of the learning technology ecosystem, including LMS/LXP, skills platforms, authoring tools, AI, coaching, content, and analytics solutions.
- Represent L&D priorities in enterprise technology and talent ecosystem decisions.
- Drive adoption and continuous improvement of digital learning experiences while ensuring scalability, integration, security, and compliance.
AI, Innovation & Transformation
- Lead adoption of approved AI, automation, and emerging technologies to transform how learning is designed, developed, delivered, and experienced.
- Establish modern design and development practices that improve personalization, accessibility, speed, quality, and productivity.
- Create a culture of experimentation, rapid iteration, and data-driven continuous improvement.
- Evaluate emerging learning capabilities and partners and scale solutions that demonstrate measurable value.
Analytics & Business Impact
- Establish measurement frameworks and KPIs for learning effectiveness, learner experience, capability development, technology adoption, operational performance, and business impact.
- Use learner, skills, operational, and business data to guide investment, design decisions, and continuous improvement.
- Provide executive-level insights on the effectiveness and value of enterprise learning investments.
Enterprise & People Leadership
- Build strong partnerships across the business, HR, Talent, DDAT/HR Technology, Information Security, Procurement, and external partners.
- Lead and develop a high-performing multidisciplinary team across learning design, digital learning, content, technology, and learner experience.
- Build team capability in learning science, AI, analytics, experience design, and emerging technologies.
- Manage resources, vendors, budgets, and investments to deliver measurable business value and operational efficiency.
Leadership & Technical Capabilities
- Enterprise learning strategy and workforce capability development
- Learning science, instructional design, curriculum architecture, and learner experience design
- Learning technology ecosystems including LMS/LXP, content, skills, AI, and analytics platforms
- AI-enabled learning design, content development, and automation
- Learning analytics, measurement, and business-impact evaluation
- Accessibility, content governance, and digital learning standards
- Strategic thinking with strong execution and transformation leadership
- Executive influence, communication, and cross-functional leadership
- Data-driven decision making and financial acumen
- Ability to lead through ambiguity and translate strategy into measurable outcomes
Location
East Coast/Midwest (preferred); Remote (open)
Required Qualifications
- 10+ years of progressive experience in learning and development, talent/capability development, learning design, or learning technology, including significant enterprise leadership experience.
- Experience developing and executing enterprise learning strategies, operating models, and large-scale transformations.
- Experience leading learning design, curriculum, content development, learner experience, or Learning Design Center of Excellence functions.
- Experience partnering with technology/product organizations to shape enterprise learning platforms and digital experiences.
- experience applying AI, automation, analytics, and emerging technology to learning and development (preferred)
- Experience leading multidisciplinary teams and managing enterprise learning demand, resources, vendors, and delivery.
- Proven ability to influence senior executives and lead effectively across complex, cross-functional organizations. Travel - 1 week/month to and/or based on the needs of the business
Preferred Qualifications
Please replace this section with the Preferred Job Qualifications
Education
- Bachelor's degree (required)
- Master's degree in Learning, Organizational Development, Human Resources, Education, Instructional Design, Business, Technology, or related field (preferred)
Pay Range
The typical pay range for this role is:
$131,500.00 - $303,195.00
This pay range represents the base hourly rate or base annual full-time salary for all positions in the job grade within which this position falls. The actual base salary offer will depend on a variety of factors including experience, education, geography and other relevant factors. This position is eligible for a CVS Health bonus, commission or short-term incentive program in addition to the base pay range listed above. This position also includes an award target in the company’s equity award program.
Our people fuel our future. Our teams reflect the customers, patients, members and communities we serve and we are committed to fostering a workplace where every colleague feels valued and that they belong.
Great benefits for great people
We take pride in offering a comprehensive and competitive mix of pay and benefits that reflects our commitment to our colleagues and their families.
This full‑time position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial well‑being of colleagues and their families. The benefits for this position include medical, dental, and vision coverage, paid time off, retirement savings options, wellness programs, and other resources, based on eligibility.
Additional details about available benefits are provided during the application process and on Benefits Moments.
We anticipate the application window for this opening will close on: 12/18/2026
Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.
We’re building a world of health around every individual — shaping a more connected, convenient and compassionate health experience. At CVS Health®, you’ll be surrounded by passionate colleagues who care deeply, innovate with purpose, hold ourselves accountable and prioritize safety and quality in everything we do. Join us and be part of something bigger – helping to simplify health care one person, one family and one community at a time.
Position Summary
The Executive Director, Head of Learning Strategy, Design & Learner Experience is a member of the Learning & Development Leadership Team responsible for shaping and executing the enterprise learning strategy and creating modern, high-impact learning experiences that build workforce capability and support business performance.
This leader oversees learning strategy, enterprise learning design, curriculum and content, learner experience, learning technology strategy, AI-enabled learning, analytics, and the Learning Design Center of Excellence. In close partnership with DDAT/HR Technology, the role translates L&D priorities and learner needs into the technology capabilities and digital experiences required to enable them.
The role sets enterprise standards and drives innovation across the learning ecosystem, improving quality, speed, scalability, accessibility, learner experience, and business impact while simplifying how learning is designed and delivered.
Key Responsibilities
Enterprise Learning Strategy & Governance
- Define and execute the enterprise learning strategy and multi-year roadmap aligned with business, talent, skills, and workforce priorities.
- Establish enterprise standards and governance for learning design, curriculum architecture, content, accessibility, learner experience, and measurement.
- Translate business and workforce capability needs into scalable learning strategies and solutions.
- Serve as a strategic advisor to senior leaders on learning, skills, AI, and workforce capability trends.
Learning Design & Learner Experience
- Lead the Learning Design Center of Excellence and end-to-end design and development of enterprise learning experiences across digital, virtual, instructor-led, multimedia, performance support, immersive, and AI-enabled modalities.
- Establish modern learning design and learner experience principles grounded in learning science, accessibility, user experience, and measurable performance outcomes.
- Drive consistency, quality, reuse, modularity, and scalability across enterprise curricula and content.
- Lead the strategy and learner experience for Classroom of the Future, partnering with DDAT on enabling technology products and capabilities.
- Oversee learning demand, prioritization, capacity, and delivery to balance strategic initiatives with ongoing business and regulatory needs.
Learning Technology & Digital Enablement
- Serve as L&D's strategic partner to DDAT/HR Technology, translating learning and learner experience requirements into technology capabilities and roadmaps.
- Partner on the strategy, governance, selection, optimization, and evolution of the learning technology ecosystem, including LMS/LXP, skills platforms, authoring tools, AI, coaching, content, and analytics solutions.
- Represent L&D priorities in enterprise technology and talent ecosystem decisions.
- Drive adoption and continuous improvement of digital learning experiences while ensuring scalability, integration, security, and compliance.
AI, Innovation & Transformation
- Lead adoption of approved AI, automation, and emerging technologies to transform how learning is designed, developed, delivered, and experienced.
- Establish modern design and development practices that improve personalization, accessibility, speed, quality, and productivity.
- Create a culture of experimentation, rapid iteration, and data-driven continuous improvement.
- Evaluate emerging learning capabilities and partners and scale solutions that demonstrate measurable value.
Analytics & Business Impact
- Establish measurement frameworks and KPIs for learning effectiveness, learner experience, capability development, technology adoption, operational performance, and business impact.
- Use learner, skills, operational, and business data to guide investment, design decisions, and continuous improvement.
- Provide executive-level insights on the effectiveness and value of enterprise learning investments.
Enterprise & People Leadership
- Build strong partnerships across the business, HR, Talent, DDAT/HR Technology, Information Security, Procurement, and external partners.
- Lead and develop a high-performing multidisciplinary team across learning design, digital learning, content, technology, and learner experience.
- Build team capability in learning science, AI, analytics, experience design, and emerging technologies.
- Manage resources, vendors, budgets, and investments to deliver measurable business value and operational efficiency.
Leadership & Technical Capabilities
- Enterprise learning strategy and workforce capability development
- Learning science, instructional design, curriculum architecture, and learner experience design
- Learning technology ecosystems including LMS/LXP, content, skills, AI, and analytics platforms
- AI-enabled learning design, content development, and automation
- Learning analytics, measurement, and business-impact evaluation
- Accessibility, content governance, and digital learning standards
- Strategic thinking with strong execution and transformation leadership
- Executive influence, communication, and cross-functional leadership
- Data-driven decision making and financial acumen
- Ability to lead through ambiguity and translate strategy into measurable outcomes
Location
East Coast/Midwest (preferred); Remote (open)
Required Qualifications
- 10+ years of progressive experience in learning and development, talent/capability development, learning design, or learning technology, including significant enterprise leadership experience.
- Experience developing and executing enterprise learning strategies, operating models, and large-scale transformations.
- Experience leading learning design, curriculum, content development, learner experience, or Learning Design Center of Excellence functions.
- Experience partnering with technology/product organizations to shape enterprise learning platforms and digital experiences.
- experience applying AI, automation, analytics, and emerging technology to learning and development (preferred)
- Experience leading multidisciplinary teams and managing enterprise learning demand, resources, vendors, and delivery.
- Proven ability to influence senior executives and lead effectively across complex, cross-functional organizations. Travel - 1 week/month to and/or based on the needs of the business
Preferred Qualifications
Please replace this section with the Preferred Job Qualifications
Education
- Bachelor's degree (required)
- Master's degree in Learning, Organizational Development, Human Resources, Education, Instructional Design, Business, Technology, or related field (preferred)
Pay Range
The typical pay range for this role is:
$131,500.00 - $303,195.00
This pay range represents the base hourly rate or base annual full-time salary for all positions in the job grade within which this position falls. The actual base salary offer will depend on a variety of factors including experience, education, geography and other relevant factors. This position is eligible for a CVS Health bonus, commission or short-term incentive program in addition to the base pay range listed above. This position also includes an award target in the company’s equity award program.
Our people fuel our future. Our teams reflect the customers, patients, members and communities we serve and we are committed to fostering a workplace where every colleague feels valued and that they belong.
Great benefits for great people
We take pride in offering a comprehensive and competitive mix of pay and benefits that reflects our commitment to our colleagues and their families.
This full‑time position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial well‑being of colleagues and their families. The benefits for this position include medical, dental, and vision coverage, paid time off, retirement savings options, wellness programs, and other resources, based on eligibility.
Additional details about available benefits are provided during the application process and on Benefits Moments.
We anticipate the application window for this opening will close on: 12/18/2026
Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.
See All 21 Head of Learning Jobs
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Find Head of Learning JobsHead of Learning Job Market
Who's Hiring
Top Industries Hiring
- Technology & Software
What Employers Look For
The qualifications that appear most often in head of learning jobs.
- Bachelor's or master's degree in instructional design, education, or organizational development
- Proven experience designing and managing enterprise learning and development programs
- Proficiency with an LMS platform such as Cornerstone, Workday Learning, or similar
- Experience leading a team of instructional designers, trainers, or L&D specialists
- Ability to measure learning effectiveness using data and report results to senior leadership
- Familiarity with adult learning theory and modern instructional design methodologies
Tips for Your Head of Learning Job Search
Align your resume to business outcomes
Head of learning hiring managers want to see how your programs moved the needle on retention, productivity, or revenue. Rewrite your bullet points to show what changed after each initiative you led, not just what you built or launched.
Highlight your learning tech stack
Most postings list a specific LMS, authoring tool, or analytics platform. Name the tools you've used in your resume header or a dedicated skills section so your application clears initial filters before anyone reads your summary.
Target roles by organizational maturity
A startup head of learning builds the function from scratch, while an enterprise role inherits a large team and existing curriculum. Read each job description for language like 'build' versus 'scale' to match your experience to what the employer actually needs.
Apply early to roles that fit
Migrate Mate lists head of learning openings from across the United States in one place, so you can find roles that match and apply directly to each listing.
Prepare a portfolio of program impact
Bring two or three case studies to every interview: the business problem, your instructional approach, and the measurable result. Hiring committees for this role routinely ask you to walk through past work rather than answer hypothetical questions alone.
Negotiate scope before discussing compensation
Clarify reporting structure, headcount, and budget authority in a final-round conversation before salary comes up. The scope of a head of learning role varies enormously between organizations, and understanding it first gives you a stronger basis for whatever you negotiate next.
Head of Learning Jobs: Frequently Asked Questions
Which companies are hiring the most head of learnings?
The most active employers for head of learnings right now are CVS Health, Duolingo, and Dartmouth College, and the most openings are in Florida, New York, and Maryland, based on current listings on Migrate Mate as of November 2026. Healthcare systems, large technology companies, and financial services firms tend to post the highest volume of these roles year-round.
How many head of learning jobs are remote?
About 64% of head of learning openings are fully remote or hybrid as of November 2026, reflecting how much of the work centers on program design and virtual facilitation rather than in-person delivery. Roles focused on e-learning strategy and technology implementation tend to be the most remote-friendly, while positions tied to hands-on leadership development or culture change often require more on-site presence.
How do you become a head of learning?
Most people reach this role by moving through individual contributor positions in instructional design or facilitation, then into a manager or director of learning and development role where they oversee a team and own program strategy. Building a portfolio of programs that produced measurable business results, earning a credential such as a CPTD or a master's in organizational development, and gaining experience managing learning technology platforms all strengthen your candidacy for a head of learning title.
Can I get a head of learning role without direct L&D management experience?
Some organizations will hire a strong instructional design lead or a training manager into a head of learning role if the company is early in building its L&D function and needs someone to establish it rather than inherit a team. Your best path is to demonstrate that you have influenced learning strategy across a business unit, managed vendor or contractor relationships, and reported program outcomes to senior stakeholders, even if you haven't held a direct management title yet.
What does the head of learning interview process look like?
Most processes include an initial screening call with a recruiter, a competency interview with the CHRO or VP of people, and a panel conversation with cross-functional stakeholders such as business unit leaders or the IT team that owns the LMS. Many employers add a presentation round where you walk through a learning strategy you've built or propose one for a challenge they give you in advance. Reference checks typically follow the final panel before an offer is extended.
Where can I find and apply to head of learning jobs?
You can find and apply to head of learning jobs on Migrate Mate, which lists current openings from across the United States. Find the roles that fit your experience and seniority level, then apply directly to each listing from the page.
See All 21 Head of Learning Jobs
Find roles that match your experience and apply in just a few clicks.
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