Remote Head Instructor Jobs
Remote Head Instructor jobs are open across the U.S. at remote-first firms and distributed teams in education technology, corporate training, and professional development. Employers hiring remotely right now include Pavago, boi, and Respiris. See the openings below and apply to the ones that match your experience.
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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 336+ Remote Head Instructor Jobs
Find roles that match your experience and apply in just a few clicks.
Find Remote Head Instructor JobsRemote Head Instructor Job Market
Who's Hiring
Top Industries Hiring
- Staffing & Recruiting
- Technology & Software
- Science & Research
- Agriculture & Farming
- Banking & Financial Services
What Employers Look For
The qualifications that appear most often in remote head instructor jobs.
- Demonstrated experience leading or managing a team of instructors or coaches
- Current certification in the relevant discipline such as ACE, NASM, ATA, or equivalent
- Proven ability to design and implement curriculum or structured training programs
- CPR and first aid certification, current and from an accredited organization
- Strong classroom or floor management skills with groups of varying skill levels
- Bachelor's degree in education, kinesiology, physical education, or a related field
Tips for Your Remote Head Instructor Job Search
Show your async communication skills upfront
Remote head instructors direct teams and learners without in-person contact, so demonstrate written clarity early. Include a sample async update, instructor brief, or curriculum memo in your application materials to show you can lead through documentation.
Apply early to remote roles that fit
Migrate Mate lists remote head instructor openings from across the U.S. in one place, so you can find roles that match your background and apply directly without sorting through unrelated listings.
Build a portfolio of programs you have led
Remote employers want evidence of independent program leadership. Compile curriculum outlines, instructor onboarding materials, or completion and outcome data from programs you have run to give hiring managers something concrete to evaluate before the interview.
Prepare for a remote teaching demonstration
Many remote head instructor interviews include a live virtual teaching or coaching demo. Practice delivering instruction clearly over video, managing engagement without physical presence, and using screen sharing or collaborative tools to walk through curriculum structure.
Remote Head Instructor Jobs: Frequently Asked Questions
How do I get a remote head instructor job?
Target remote-first education technology companies, online learning platforms, and distributed corporate training teams, as these organizations hire head instructors remotely most consistently. Remote employers screen for strong written communication, the ability to manage curriculum and instructors without in-person oversight, and comfort with async collaboration tools. A portfolio of programs you have built or led gives you a clear edge over candidates with equivalent credentials.
Which companies hire remote head instructors?
Companies hiring remote head instructors right now include Pavago, boi, and Respiris, based on current remote listings on Migrate Mate as of November 2026. These tend to be remote-first edtech platforms, distributed professional training organizations, and online bootcamps that run instruction programs across multiple time zones.
Can you get a remote head instructor job with no experience?
Yes, but remote entry-level head instructor roles are harder to land because employers expect you to manage curriculum, instructors, or programs independently from day one. Online bootcamps and edtech startups are the most likely to hire candidates with limited formal experience. Showing a self-directed project, volunteer teaching leadership, or a structured curriculum you built yourself can open doors that a resume alone will not.
Do you need a degree for remote head instructor jobs?
Not always. Remote employers weigh demonstrated instructional leadership and program results heavily alongside formal credentials. A portfolio of curricula you have designed, measurable outcomes from programs you have led, and subject-matter depth in the relevant field often carry more weight than a specific degree. Some roles, particularly in K-12 or regulated professional training, do require specific credentials, so check each listing carefully.
Which industries hire the most remote head instructors?
Most remote head instructor openings sit in Staffing & Recruiting, Technology & Software, and Science & Research, per current remote listings on Migrate Mate as of November 2026. These sectors rely on distributed teams to deliver training and instruction at scale, making the head instructor role a natural fit for fully remote or hybrid structures.
See All 336+ Remote Head Instructor Jobs
Find roles that match your experience and apply in just a few clicks.
Find Remote Head Instructor Jobs