Learning Experience Trainer (Remote Eligible Costa Rica)

Company: Smartsheet
Location: San Jose
Posted on: April 1, 2026

Job Description:

For over 20 years, Smartsheet has helped people and teams achieve–well, anything. From seamless work management to smart, scalable solutions, we’ve always worked with flow. We’re building tools that empower teams to automate the manual, uncover insights, and scale smarter. But more than that, we’re creating space– space to think big, take action, and unlock the kind of work that truly matters. Because when challenge meets purpose, and passion turns into progress, that’s magic at work, and it’s what we show up for everyday. Smartsheet is looking for an enthusiastic Learning Experience Trainer who will develop, prepare, deliver, and evaluate technical training curricula and programs for our Customer Excellence Teams. This role outlines and coordinates documentation and materials for programs, designs exercises to enhance lectures, and conducts classes with hands-on exercises. This role also develops, maintains, and improves exams and quizzes utilized in all training courses. You will develop technical training programs and help others develop skills that will make them better professionals and customer advocates. Learning Experience trainers must be extremely knowledgeable in their field and possess strong technical aptitude. Additionally, we expect you to be an excellent communicator, able to explain complex subjects clearly and engagingly, and to help develop people’s technical skills to meet organizational needs. This role will report directly to the Manager, CE Learning. This role is eligible for remote work within Costa Rica. You must reside in Costa Rica. You will: Devising technical training programs according to organizational requirements Producing training schedules and classroom agendas Determining course content according to objectives Building ad-hoc training materials to ensure the learner has the tools to be successful Delivering technical training to Smartsheet’s technical customer-facing teams Attending product release training, testing new product functionality, and staying up-to-date on product enhancements and releases Creating/delivering technical training materials for new products, product releases, and feature updates. Execute training sessions, webinars, workshops, etc., in groups or individually. Arrange for and conduct on-site training when needed Keep and report data on completed courses, absences, issues, and related details. Observe and evaluate the results of training programs Determine the overall effectiveness of programs and make improvements Assess training needs and certification requirements for technical resources at various levels. Other job duties as assigned. You have: Proven experience as a technical trainer Knowledge of modern training techniques and tools in technical subjects Experience in designing technical course content Ability to address training needs with complete courses Outstanding communication skills and comfortable speaking to crowds Strong Command of the English language, both oral and written (C1 and above) Excellent organizational and time-management abilities Degree in a relevant technical field Experience using Articulate 360 and/or Vyond is a strong asset Strong working knowledge of Smartsheet is preferred but not required (Smartsheet product certification is a plus). Bonus points for: Certified Technical Training credential (CTT), ATD Adult Learning Certificate, or equivalent Project and process management skills. PMP is an added benefit. Perks & Benefits: Fully paid Health & Life insurance for full-time employees and family members Monthly stipend to support your work and productivity 12 days paid Vacation Flexible Time Away Program 20 weeks fully paid Maternity Leave 12 weeks fully paid Paternity/Adoption Leave Personal paid Volunteer Day to support our community Opportunities for professional growth and development including access to LinkedIn Learning online courses Company Funded Perks including a counseling membership and your own personal Smartsheet account Teleworking options from any registered location in Costa Rica (role specific) 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, and India. 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

Keywords: Smartsheet, Sunnyvale , Learning Experience Trainer (Remote Eligible Costa Rica), IT / Software / Systems , San Jose, California