Remote Life Skills Trainer Jobs
Remote Life Skills Trainer jobs are open across education, human services, behavioral health, and workforce development at remote-first organizations, nonprofits, and distributed service providers nationwide. Employers currently hiring include Terraboost Media, Robert Half, and VC Lab, with openings from entry-level trainers to senior program leads. Scan the live roles below and apply to whichever ones fit.
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Showing 5 of 64+ Remote Life Skills Trainer 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 64 Remote Life Skills Trainer Jobs
Find roles that match your experience and apply in just a few clicks.
Find JobsRemote Life Skills Trainer Job Market
Who's Hiring
- Terraboost Media56
- Robert Half2
- VC Lab1
- ANTHROPOS1A
- Smartsheet1
What Employers Look For
The qualifications that appear most often in remote life skills trainer jobs.
- High school diploma or associate degree, with a bachelor's degree preferred for senior roles
- Experience supporting individuals with developmental disabilities, mental health diagnoses, or similar populations
- Valid driver's license and reliable transportation to transport or accompany clients
- CPR, First Aid, and crisis intervention certification such as CPI or Mandt
- Ability to document service delivery, progress notes, and goal tracking in electronic health records
- Knowledge of independent living skills curriculum covering budgeting, cooking, hygiene, and community navigation
Tips for Your Remote Life Skills Trainer Job Search
Apply early to remote roles that fit
Migrate Mate lists remote life skills trainer openings from across the U.S. in one place, so you can find roles that match your background and apply directly without sorting through location-based listings that don't apply to you.
Show your virtual facilitation experience clearly
Remote employers want proof you can run sessions without an in-person room. Call out specific video platforms you've used, the populations you've trained virtually, and any async tools like digital workbooks or recorded modules you've built or delivered.
Demonstrate strong written communication skills
Remote life skills trainer roles depend heavily on written handoffs, case notes, and client communication. Your cover letter and any work samples are your first proof of this, so write in plain, direct language and make every sentence count.
Prepare for competency-based remote interviews
Remote hiring teams often run video interviews focused on specific scenarios, such as how you'd handle a disengaged virtual client or coordinate with a distributed case management team. Practice answering in concrete terms with specific examples from past work.
Remote Life Skills Trainer Jobs: Frequently Asked Questions
How do I get a remote life skills trainer job?
Target organizations that already run distributed service delivery, such as virtual behavioral health platforms, online education providers, and remote workforce development programs, because they have established systems for remote life skills work. Remote employers screen heavily for self-direction, clear written communication, and the ability to engage clients effectively through video tools. Demonstrating that you've run virtual sessions, documented client progress independently, or trained across digital platforms gives you a concrete edge over candidates without that remote experience.
Which companies hire remote life skills trainers?
Employers currently hiring remote life skills trainers include Terraboost Media, Robert Half, and VC Lab, per current remote listings on Migrate Mate as of November 2026. These tend to be remote-first behavioral health companies, distributed education nonprofits, and virtual workforce development programs that deliver services entirely online.
Can you get a remote life skills trainer 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 supervision. Nonprofits, online tutoring platforms, and community outreach organizations sometimes hire entry-level remote life skills trainers. You can strengthen your candidacy by showing volunteer facilitation, documented client outcomes from coursework or practicum hours, and comfort with video conferencing and case management tools.
Do you need a degree for remote life skills trainer jobs?
Not always. Many remote employers prioritize demonstrated facilitation skills, relevant certifications, and a history of working with specific populations over a formal degree. Human services certificates, peer specialist credentials, or documented experience supporting individuals with disabilities, youth, or reentry populations can carry real weight. That said, roles within behavioral health systems or government-funded programs often require at minimum an associate or bachelor's degree in a related field.
See All 64 Remote Life Skills Trainer Jobs
Find roles that match your experience and apply in just a few clicks.
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