Remote Head of Strategy and Operations Jobs
Remote Head of Strategy and Operations jobs are open across the U.S. at remote-first firms, distributed tech companies, and venture-backed startups that run on async workflows. Demand is active in sectors like SaaS, fintech, healthcare, and professional services, with employers including CVS Health, Directive, and Advantage HQ hiring now. Scan the live roles below and apply to whichever ones fit.
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Showing 5 of 25+ Remote Head of Strategy and Operations jobs
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.
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Find JobsRemote Head of Strategy and Operations Job Market
Who's Hiring
Top Industries Hiring
- Technology & Software
What Employers Look For
The qualifications that appear most often in remote head of strategy and operations jobs.
- 7-12 years of experience in strategy, operations, consulting, or a related field
- Demonstrated ability to lead cross-functional initiatives without direct authority
- Strong financial modeling and data analysis skills, often including SQL or advanced Excel
- Experience building or improving operational processes and internal reporting systems
- MBA or equivalent graduate degree, particularly from a business or public policy program
- Comfort presenting to and influencing senior executives and board-level stakeholders
Tips for Your Remote Head of Strategy and Operations Job Search
Apply early to remote roles that fit
Migrate Mate lists remote head of strategy and operations openings from across the U.S. in one place. Search for roles that match your background and apply directly, without sifting through listings that require on-site work.
Show async leadership in your application materials
Remote employers want proof you can align stakeholders without meetings. Include writing samples, strategic memos, or documented process changes in your application to show you lead through clear, structured communication rather than presence.
Build a results portfolio before you apply
Compile two or three concise case studies covering OKR cycles you ran, operating models you built, or cross-functional initiatives you owned. Remote hiring managers read these instead of calling references, so concrete artifacts close the credibility gap fast.
Prepare for remote-specific interview questions
Remote panels for this role almost always ask how you maintain alignment across distributed functions and how you handle ambiguity without escalating. Practice answers that name specific tools you've used, like Notion or Loom, and walk through a real async decision you drove.
Remote Head of Strategy and Operations Jobs: Frequently Asked Questions
How do I get a remote head of strategy and operations job?
Remote employers hiring for this role screen hard for self-direction, structured written communication, and the ability to drive cross-functional initiatives without in-person oversight. Candidates who stand out show concrete examples of building operating cadences, running strategic planning cycles, and communicating decisions asynchronously. Familiarity with tools like Notion, Confluence, or Loom signals you can lead distributed teams effectively from day one.
Which companies hire remote head of strategy and operationss?
Employers currently hiring remote head of strategy and operationss include CVS Health, Directive, and Advantage HQ, per current remote listings on Migrate Mate as of November 2026. Remote-first SaaS companies, distributed fintech firms, and venture-backed startups with globally distributed teams are among the most consistent employers of this role.
Can you get a remote head of strategy and operations job with no experience?
Yes, but remote roles at this level are competitive because companies expect you to operate independently with minimal onboarding support. Entry paths include chief of staff roles at remote-first startups, ops lead positions at early-stage companies, or consulting projects you can document as results. Showing a portfolio of process improvements, strategic memos, or cross-functional projects you owned goes further than credentials alone.
Do you need a degree for remote head of strategy and operations jobs?
Not always. Remote employers in this category weigh demonstrated results over formal credentials, especially at growth-stage companies where outcomes matter more than pedigree. A history of owning OKR cycles, building operating models, or scaling team processes remotely can outweigh an MBA, particularly if you can show the work in a portfolio or case study format.
Which industries hire the most remote head of strategy and operationss?
Most remote head of strategy and operations openings sit in Technology & Software, per current remote listings on Migrate Mate as of November 2026. These sectors rely on distributed leadership teams that need someone coordinating strategy and execution across time zones without a central office.
See All 25 Remote Head of Strategy and Operations Jobs
Find roles that match your experience and apply in just a few clicks.
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