Remote Life Skills Teacher Jobs
Remote Life Skills Teacher jobs are open across the U.S. in special education, adult education, nonprofit services, and behavioral health, with positions from entry-level instructors to senior curriculum designers. Organizations hiring remotely right now include Terraboost Media, VC Lab, and ANTHROPOS. Scan the live roles below and apply to whichever ones fit.
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Showing 5 of 63+ Remote Life Skills Teacher jobs
For over 20 years, Smartsheet has empowered teams to manage work seamlessly and scale solutions smarter. Now, in our most ambitious chapter yet, we are uniting human teams with AI agents. By orchestrating the work agents do best, automating manual tasks and uncovering insights at scale, we create the space for people to focus on what truly matters: judgment, creativity, and big thinking. That is magic at work, and it's what we show up for every day.
The Revenue Enablement Director, Technical Skills Enablement leads the Technical Skills track of Role Excellence. You will build and run the strategy that gives Solution Engineers, Customer Success Managers, and Professional Services consultants the platform and solution competence to drive demonstrated customer outcomes. You will be a deeply technical, strategic leader and executive influencer who earns credibility with Product, Engineering, and field leaders alike.
Technical depth is critical to the customer engagement journey, and it is what turns a sold solution into realized outcomes. You will ensure customer-facing teams can competently use AI and FDE solutions and the Smartsheet platform to design, demonstrate, deploy, and optimize solutions with confidence.
This is a build-the-future role, not a maintain-the-program role. We are reshaping how customer-facing teams are prepared to win and retain customers as AI changes how customers buy, evaluate, and use execution management platforms. You will define the strategic, future capabilities of your Center of Enablement Excellence, moving from event-based enablement to always-on, data-driven, proficiency-aware skilling measured by revenue attainment, and lead a team and a set of cross-functional partners to make it real at scale.
In 2005, Smartsheet was founded on the idea that teams and millions of people worldwide deserve a better way to deliver their very best work. Today, we deliver a leading cloud-based platform for work execution, empowering organizations to plan, capture, track, automate, and report on work at scale, resulting in more efficient processes and better business outcomes.
Our mission in GTM Enablement: we build confidence and competence in customer-facing roles so they can deliver customer value and drive revenue and retention.
This Director role reports to the VP of Revenue Enablement.
You Will:
- Own the Technical enablement strategy, hands-on experiences, and reinforcement for customer-facing roles, graduated by role and proficiency: platform and solution competence, technical envisioning, demo and proof of concept, solution design/delivery, product and security narrative, and outcome realization.
- Build a technically authoritative enablement capability and scenario-based assessment, that keeps pace with a rapidly evolving platform and AI portfolio.
- Lead the technical content capability, and partner with Customer Education and Product so internal and customer-facing technical learning are consistent and non-duplicative.
- Drive predictable, role-specific technical skilling for prioritized GTM plays tied to product General Availability, covering pre-, at-, and post-GA moments.
- Collaborate deeply with the Consultative Skills CoE so technical and consultative capabilities are orchestrated seamlessly in customer conversations.
- Equip managers, through the Manager / Leader Enablement CoE, to assess and coach technical proficiency in their teams.
- Drive measurable proficiency outcomes tied to revenue (e.g., technical win rate, deal velocity, solution attach, time to first customer value, adoption, and net retention) and report them to senior leadership.
- Set the strategy and own the outcomes for your Center of Enablement Excellence, translating company OKRs and GTM priorities into a clear multi-quarter roadmap with defined behavior-change and business-impact metrics.
- Operate as a strategic leader and executive influencer: shape priorities with Directors, VPs, and SVPs across Sales, Customer Success, Professional Services, Product, and People, and secure alignment and investment through data and business cases.
- Build and lead a high-performing team; hire, coach, and develop leaders, set a high bar for execution, and foster an inclusive, accountable culture.
- Drive execution with rigor: run a predictable operating cadence, manage budget, headcount, vendors, and priorities, and deliver on commitments at scale across geographies.
- Apply AI and modern learning technology to scale: partner with the AI-Based Content Creation & Experiences CoE and the enablement tech stack to deliver just-in-time, proficiency-aware skilling experiences.
- Partner as one team with fellow CoE Directors to deliver a seamless, end-to-end capability journey, with clean hand-offs and no gaps or duplication for the roles we serve.
You Have:
- Technical credibility in SaaS, work management, automation, or enterprise platforms, ideally from experience leading or building solution engineering, customer success, or professional services teams.
- Experience designing hands-on technical learning, certification, and validation programs at scale.
- The ability to translate complex product and architecture concepts for a range of audiences, and to partner credibly with Engineering and Product leaders.
- 12+ years of experience in enablement, learning and development, sales or customer-facing operations, or a closely related discipline in a high-growth SaaS or technology company.
- 6+ years of experience leading managers and/or senior individual contributors, with a record of building, developing, and retaining high-performing teams.
- Demonstrated ability to influence and partner with senior and executive stakeholders, including VP and SVP leaders, and to align cross-functional teams without direct authority.
- Proven strategic thinking and execution: a history of turning an ambiguous vision into a scaled, measured program that changed behavior and moved business results.
- Experience building programs on a competency or proficiency framework, and using data to link enablement investment to business outcomes (required).
- Proven record of leading teams and working in environments strongly focused on sales and metric driven roles (e.g., ARR, Pipeline).
- Prior success building AI and FDE solution fluency across SE, CS, and PS roles to drive measurable business outcomes.
- A track record of improving field proficiency and customer outcomes with data.
- Strong command of adult learning principles, modern enablement technology, and AI-enabled content and delivery.
- Executive-level communication, storytelling, and presentation skills, with sound judgment and a bias to action in a fast-moving environment.
- Experience managing budgets, vendors, and global programs across time zones.
- BA/BS required; MBA or advanced degree preferred, or equivalent experience.
Get to Know Us:
At Smartsheet, your ideas are heard, your potential is supported, and your contributions have real impact. You'll have the freedom to explore, push boundaries, and grow beyond your role. We welcome diverse perspectives and nontraditional paths—because we know that impact comes from individuals who care deeply and challenge thoughtfully. When you're doing work that stretches you, excites you, and connects you to something bigger, that's magic at work. Let's build what's next, together.
Equal Opportunity Employer:
Smartsheet is an Equal Opportunity (EEO) employer committed to fostering an inclusive environment with the best employees. It is our policy to provide equal employment opportunities to all qualified applicants in accordance with applicable laws in the US, UK, Australia, Germany, Costa Rica, Japan, Bulgaria, India, and Singapore. All qualified applicants will receive consideration without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran or disabled status, or genetic information.
If there are preparations we can make to help ensure you have a comfortable and positive interview experience, please let us know.
#LI-Remote
For over 20 years, Smartsheet has empowered teams to manage work seamlessly and scale solutions smarter. Now, in our most ambitious chapter yet, we are uniting human teams with AI agents. By orchestrating the work agents do best, automating manual tasks and uncovering insights at scale, we create the space for people to focus on what truly matters: judgment, creativity, and big thinking. That is magic at work, and it's what we show up for every day.
The Revenue Enablement Director, Technical Skills Enablement leads the Technical Skills track of Role Excellence. You will build and run the strategy that gives Solution Engineers, Customer Success Managers, and Professional Services consultants the platform and solution competence to drive demonstrated customer outcomes. You will be a deeply technical, strategic leader and executive influencer who earns credibility with Product, Engineering, and field leaders alike.
Technical depth is critical to the customer engagement journey, and it is what turns a sold solution into realized outcomes. You will ensure customer-facing teams can competently use AI and FDE solutions and the Smartsheet platform to design, demonstrate, deploy, and optimize solutions with confidence.
This is a build-the-future role, not a maintain-the-program role. We are reshaping how customer-facing teams are prepared to win and retain customers as AI changes how customers buy, evaluate, and use execution management platforms. You will define the strategic, future capabilities of your Center of Enablement Excellence, moving from event-based enablement to always-on, data-driven, proficiency-aware skilling measured by revenue attainment, and lead a team and a set of cross-functional partners to make it real at scale.
In 2005, Smartsheet was founded on the idea that teams and millions of people worldwide deserve a better way to deliver their very best work. Today, we deliver a leading cloud-based platform for work execution, empowering organizations to plan, capture, track, automate, and report on work at scale, resulting in more efficient processes and better business outcomes.
Our mission in GTM Enablement: we build confidence and competence in customer-facing roles so they can deliver customer value and drive revenue and retention.
This Director role reports to the VP of Revenue Enablement.
You Will:
- Own the Technical enablement strategy, hands-on experiences, and reinforcement for customer-facing roles, graduated by role and proficiency: platform and solution competence, technical envisioning, demo and proof of concept, solution design/delivery, product and security narrative, and outcome realization.
- Build a technically authoritative enablement capability and scenario-based assessment, that keeps pace with a rapidly evolving platform and AI portfolio.
- Lead the technical content capability, and partner with Customer Education and Product so internal and customer-facing technical learning are consistent and non-duplicative.
- Drive predictable, role-specific technical skilling for prioritized GTM plays tied to product General Availability, covering pre-, at-, and post-GA moments.
- Collaborate deeply with the Consultative Skills CoE so technical and consultative capabilities are orchestrated seamlessly in customer conversations.
- Equip managers, through the Manager / Leader Enablement CoE, to assess and coach technical proficiency in their teams.
- Drive measurable proficiency outcomes tied to revenue (e.g., technical win rate, deal velocity, solution attach, time to first customer value, adoption, and net retention) and report them to senior leadership.
- Set the strategy and own the outcomes for your Center of Enablement Excellence, translating company OKRs and GTM priorities into a clear multi-quarter roadmap with defined behavior-change and business-impact metrics.
- Operate as a strategic leader and executive influencer: shape priorities with Directors, VPs, and SVPs across Sales, Customer Success, Professional Services, Product, and People, and secure alignment and investment through data and business cases.
- Build and lead a high-performing team; hire, coach, and develop leaders, set a high bar for execution, and foster an inclusive, accountable culture.
- Drive execution with rigor: run a predictable operating cadence, manage budget, headcount, vendors, and priorities, and deliver on commitments at scale across geographies.
- Apply AI and modern learning technology to scale: partner with the AI-Based Content Creation & Experiences CoE and the enablement tech stack to deliver just-in-time, proficiency-aware skilling experiences.
- Partner as one team with fellow CoE Directors to deliver a seamless, end-to-end capability journey, with clean hand-offs and no gaps or duplication for the roles we serve.
You Have:
- Technical credibility in SaaS, work management, automation, or enterprise platforms, ideally from experience leading or building solution engineering, customer success, or professional services teams.
- Experience designing hands-on technical learning, certification, and validation programs at scale.
- The ability to translate complex product and architecture concepts for a range of audiences, and to partner credibly with Engineering and Product leaders.
- 12+ years of experience in enablement, learning and development, sales or customer-facing operations, or a closely related discipline in a high-growth SaaS or technology company.
- 6+ years of experience leading managers and/or senior individual contributors, with a record of building, developing, and retaining high-performing teams.
- Demonstrated ability to influence and partner with senior and executive stakeholders, including VP and SVP leaders, and to align cross-functional teams without direct authority.
- Proven strategic thinking and execution: a history of turning an ambiguous vision into a scaled, measured program that changed behavior and moved business results.
- Experience building programs on a competency or proficiency framework, and using data to link enablement investment to business outcomes (required).
- Proven record of leading teams and working in environments strongly focused on sales and metric driven roles (e.g., ARR, Pipeline).
- Prior success building AI and FDE solution fluency across SE, CS, and PS roles to drive measurable business outcomes.
- A track record of improving field proficiency and customer outcomes with data.
- Strong command of adult learning principles, modern enablement technology, and AI-enabled content and delivery.
- Executive-level communication, storytelling, and presentation skills, with sound judgment and a bias to action in a fast-moving environment.
- Experience managing budgets, vendors, and global programs across time zones.
- BA/BS required; MBA or advanced degree preferred, or equivalent experience.
Get to Know Us:
At Smartsheet, your ideas are heard, your potential is supported, and your contributions have real impact. You'll have the freedom to explore, push boundaries, and grow beyond your role. We welcome diverse perspectives and nontraditional paths—because we know that impact comes from individuals who care deeply and challenge thoughtfully. When you're doing work that stretches you, excites you, and connects you to something bigger, that's magic at work. Let's build what's next, together.
Equal Opportunity Employer:
Smartsheet is an Equal Opportunity (EEO) employer committed to fostering an inclusive environment with the best employees. It is our policy to provide equal employment opportunities to all qualified applicants in accordance with applicable laws in the US, UK, Australia, Germany, Costa Rica, Japan, Bulgaria, India, and Singapore. All qualified applicants will receive consideration without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran or disabled status, or genetic information.
If there are preparations we can make to help ensure you have a comfortable and positive interview experience, please let us know.
#LI-Remote
See All 63 Remote Life Skills Teacher Jobs
Find roles that match your experience and apply in just a few clicks.
Find JobsRemote Life Skills Teacher Job Market
Who's Hiring
- Terraboost Media56
- VC Lab1
- ANTHROPOS1A
- Smartsheet1
- Robert Half1
What Employers Look For
The qualifications that appear most often in remote life skills teacher jobs.
- State-issued special education teaching license or certification for the grade band
- Experience writing and implementing Individualized Education Programs for students with disabilities
- Knowledge of functional life skills curriculum frameworks and community-based instruction
- Ability to collaborate with paraprofessionals, families, and transition service agencies
- Experience with assistive technology tools and augmentative communication devices
- Bachelor's degree in special education, human services, or a closely related field
Tips for Your Remote Life Skills Teacher Job Search
Show your virtual teaching toolkit upfront
Remote life skills employers want to see you can deliver structured instruction without in-person presence. Name the platforms you use, such as Zoom, Google Classroom, or Nearpod, and describe how you adapt hands-on activities for a virtual format in your resume summary.
Demonstrate async communication in every application
Remote life skills teachers communicate progress updates, behavior notes, and lesson feedback entirely through written channels. Write your cover letter and email responses with the same clarity and structure you would bring to a student IEP summary, because hiring managers read them as a sample of your daily work.
Apply early to remote roles that fit
Migrate Mate lists remote life skills teacher openings from across the U.S. in one place, so you can find roles that match your population focus and apply directly without sorting through unrelated postings.
Build a portfolio of remote-ready lesson artifacts
Collect lesson plans designed for virtual delivery, screenshots of digital student progress trackers, and any recorded session excerpts you have permission to share. Remote employers hiring life skills teachers are evaluating whether your materials translate outside a physical classroom.
Remote Life Skills Teacher Jobs: Frequently Asked Questions
How do I get a remote life skills teacher job?
Target organizations that already run distributed programs, such as remote charter schools, online adult education providers, and virtual behavioral health platforms. Remote employers screen for self-direction, clear written communication, and the ability to deliver engaging instruction through video tools like Zoom or Teams. A portfolio of lesson plans, student progress documentation, or recorded virtual sessions gives your application a concrete edge over candidates with similar credentials.
Which companies hire remote life skills teachers?
Remote life skills teacher roles are posted by Terraboost Media, VC Lab, and ANTHROPOS and others right now, based on current remote listings on Migrate Mate as of November 2026. Hiring tends to concentrate at remote-first education companies, distributed nonprofit service organizations, and virtual behavioral health and special education providers.
Can you get a remote life skills teacher job with no experience?
Yes, but remote entry-level roles are harder to land because employers expect you to work independently from day one with minimal oversight. Volunteer facilitation work, practicum hours with community organizations, or self-directed online tutoring all serve as substitutes for formal experience. Candidates who can demonstrate structured lesson planning, written student communication, and reliable async follow-through open the most doors at remote-first organizations hiring at the entry level.
Do you need a degree for remote life skills teacher jobs?
Not always, though many remote employers prefer a degree in education, social work, psychology, or a related field. What remote hiring managers weigh heavily alongside or instead of a degree includes relevant certifications, documented work with specific populations such as adults with disabilities or at-risk youth, and demonstrated ability to design and deliver structured curriculum in a virtual setting.
See All 63 Remote Life Skills Teacher Jobs
Find roles that match your experience and apply in just a few clicks.
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