[All remote jobs](https://jobicy.com/jobs.md)Open role[![Smartsheet logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/8b6103bd-221.jpg)](https://jobicy.com/company/smartsheet.md)Remote opportunity at[Smartsheet](https://jobicy.com/company/smartsheet.md) # Technical Support Specialist II – Core Apps (Costa Rica) Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/smartsheet.md)Share1 Aug 2026Published629Listing views68Application actions1 Sep 2026Apply before Opportunity details ## About this role. AI SummarySmartsheet is seeking a Technical Support Specialist II to join their global support team. This role involves troubleshooting customer issues, becoming product certified, and collaborating with team members across various channels. The ideal candidate has 1+ years of technical or customer support experience, excellent communication skills, and flexibility for non-standard hours. The position is remote within Costa Rica and offers comprehensive benefits including paid leave and professional development. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 3/5EasyHard ### Pace & Pressure 3/5RelaxedFast-paced ### Autonomy Level 3/5GuidedFull ownership ### Communication Load 4/5IndependentCollaborative AI insightThe role requires troubleshooting skills and product expertise, but is entry-level for technical support, making it moderately difficult. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job medianHighly competitive$50,000US market range$35k–$65k0$72k AI insightThe salary was not provided in the listing. Based on US market data for a Technical Support Specialist II, the median salary is estimated at $50,000. The role is remote in Costa Rica, which may adjust the local market rate. ## Core skills Skills and capabilities most closely associated with this opportunity. [Technical Support](https://jobicy.com/jobs?search_keywords=Technical%20Support.md)[Customer Service](https://jobicy.com/jobs?search_keywords=Customer%20Service.md)[Troubleshooting](https://jobicy.com/jobs?search_keywords=Troubleshooting.md)[Product Certification](https://jobicy.com/jobs?search_keywords=Product%20Certification.md)[Communication](https://jobicy.com/jobs?search_keywords=Communication.md)[Remote Work](https://jobicy.com/jobs?search_keywords=Remote%20Work.md)[Problem Solving](https://jobicy.com/jobs?search_keywords=Problem%20Solving.md)[Team Collaboration](https://jobicy.com/jobs?search_keywords=Team%20Collaboration.md)[CRM](https://jobicy.com/jobs?search_keywords=CRM.md)[Escalation Management](https://jobicy.com/jobs?search_keywords=Escalation%20Management.md) Cover letter sampleDear Hiring Manager, I am excited to apply for the Technical Support Specialist II position at Smartsheet. With over 2 years of experience in technical support, I have developed strong troubleshooting skills and a customer-first mindset. I am proficient in using various support tools and thrive in collaborative environments. I am particularly drawn to Smartsheet's mission of empowering teams through innovative work management solutions. My ability to empathize with users and resolve complex issues aligns well with the responsibilities of this role. I am eager to become product certified and contribute to your team's success. Thank you for considering my application. I look forward to the opportunity to discuss how my skills can benefit Smartsheet. Sincerely, Your Name Copy Sample interview questionsCan you describe a time when you had to troubleshoot a complex technical issue for a customer?In my previous role, a customer reported a recurring error with our software. I systematically reviewed logs, identified a configuration conflict, and provided a step-by-step solution. I also documented the issue for future reference. How do you handle a situation where you don't know the answer to a customer's question? I would first acknowledge the customer's concern, then research using available resources like documentation or escalate to a senior team member. I ensure to follow up with the customer promptly. Describe your experience with remote collaboration tools. I have used Slack, Zoom, and Jira for daily communication and project tracking. I am comfortable working asynchronously and maintaining clear documentation. How do you prioritize multiple support tickets with varying urgency? I assess each ticket based on impact and urgency, categorizing them using a priority matrix. I communicate with customers about expected resolution times and adjust as needed. Why do you want to work at Smartsheet specifically? I admire Smartsheet's innovative approach to work management and its focus on employee growth. The company's values align with my own, and I am excited to contribute to a product that helps teams achieve more. 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. Energized by solving problems and providing outstanding support? There’s never been a better time to join Smartsheet! As a Technical Support Specialist, you will report to one of our Support Team Managers and work with team members across the globe. Your responsibilities will include delivering support to our customers, maintaining high service standards, and contributing to team projects. At Smartsheet Support we empathize and empower others with expert engagements and are the first line of response for our customers to fix issues, share best practices, and advocate for users. Our teams of experts are aligned to various domains of knowledge, promoting the most effective and expedient customer resolution. This role is eligible for remote work within Costa Rica. You must reside in Costa Rica. You Will: * Troubleshoot customer issues using internal & external documentation, various tools, and other resources such as escalation resources to resolve customer issues and deliver great customer experiences * Become Smartsheet Product Certified and work with customers through a variety of channels including email, phone, and chat * Partner with leaders to meet or exceed performance goals in areas like customer satisfaction, quality assurance, and attendance * Become an expert in a specific product area * Contribute to team projects * Give and receive thoughtful feedback on team processes and leadership * Manage other responsibilities as assigned You Have: * Excellent written, verbal and interpersonal communication skills * 1+ years of Technical or Customer support experience, or equivalent * Ability to demonstrate empathetic and confident issue ownership, assuring customers that if you can’t solve their problem, you will ensure they are directed to the right resource * Working knowledge of assigned feature a plus * Flexibility in your working hours as this position will require work outside of standard business hours. 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 Show more [Apply now >](https://jobicy.com/jobs/144931-technical-support-specialist-ii-core-apps-remote-eligible-costa-rica.md) > Annual salary information is not provided for this position. 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